0:01

She basically told me all the reasons why it wouldn't

0:03

work with me. Singular talk

0:05

show host don't typically do well,

0:08

and you know they want younger, And

0:11

I said, but I am a comic like I

0:13

can make magic where there is none.

0:16

Welcome to off the cup my personal

0:19

anti anxiety antidote. As

0:22

many of you know, I've had a varied media

0:24

career where I've been able to play in a number

0:26

of sandboxes, and one of them was The

0:28

View. I

0:31

have a relationship with a View that is mixed,

0:34

mixed, we'll say mixed. I

0:36

have some wonderful memories of guest hosting the View

0:38

and in fact auditioning to be a

0:41

permanent host on the View. And I have some terrible

0:43

memories of guest hosting the View and auditioning

0:45

to be on the View.

0:47

It's not always a fun place to be.

0:49

But I have to say today's guest is

0:51

one of the bright spots for

0:53

me over the many times that I did it. She was

0:55

always so kind, so genuine, so warm,

0:58

so embracing lifting She's

1:01

also one of the funniest people I know. She

1:03

can make me laugh when I least expect it,

1:06

and in a way that I'm not expecting it,

1:08

and I know that's why people love watching her every

1:10

day now, and I'm so glad they get to.

1:13

She's an actress, a comedian, and author, a podcaster,

1:16

the Emmy Award winning future Hollywood

1:19

Walk of Fame Star winner for the Class of twenty

1:21

twenty five Daytime's Funniest host

1:24

Sherry Shephard, Welcome to Off the Cup.

1:26

Oh, I'm so glad to be here. We've been

1:28

trying to get this hook this up for the longest.

1:30

It's a it's been a busy year, but

1:33

I'm so glad we finally got this. Got

1:35

me on the books. I just adore you.

1:37

And you know what I mean about the view.

1:39

You know what I'm talking about.

1:40

Oh, absolutely, I understand. You know, you

1:42

come on there and.

1:43

As a guest host, it's

1:45

a whole different vibe and you're you know, you

1:48

got these women who have their own they

1:50

get the thing, and you're coming in with a different opinion.

1:53

Yeah, and trying to be heard. Yeah,

1:55

it's it's you know, it's a lot.

1:57

It's a lot, and I don't want to tell horror

1:59

story is I have them. But

2:02

I also just I just love

2:04

getting to work with nice women like you.

2:06

I'll focus on the positive you. Jenny

2:08

McCarthy was always so great.

2:10

I had organ too.

2:11

But can I just say, I'm so glad you

2:13

got out and got your

2:15

own spot because you deserve it.

2:18

Thank you, and you are so at

2:20

home on the Scherry

2:22

Show. It's for me.

2:24

It feels like it's one hundred percent you

2:26

were meant to do. Yeah, do you feel that way right now?

2:28

Like I am where I.

2:29

Need to be. I am where I need to

2:32

be, and this is what for me.

2:34

I've always wanted my own talk show, so this

2:36

is what I envision what I am

2:38

doing right now now.

2:39

The View was a great.

2:40

Platform for me. Barbara

2:43

Walters was a wonderful mentor who

2:45

helped me find my voice so that I could,

2:48

you know, take that over here to my show and

2:51

you know, they all the ladies were great

2:53

and that was a great experience.

2:55

But this is for Sherry.

2:58

That was I was just I was one of

3:00

many posts, you

3:02

know, for that season.

3:04

That's seven years all you. This is

3:06

all me you, and what I love is it's

3:10

all of you.

3:10

It's your funny side,

3:13

which obviously you lead with because you're so

3:15

funny you, but it's your

3:17

heart.

3:18

It's your family.

3:19

It's all the things about you

3:21

that you get to do on this show.

3:23

It's so funny because when I do the

3:25

view, I would always have a story about.

3:27

My son Jeffrey.

3:28

I did it from the time he was two years old

3:30

up until he was about ten, I

3:33

think, and I always.

3:34

Had a story.

3:35

And I remember Barbara Walter said

3:37

to me one day when another

3:39

Jeffrey story, and

3:42

I said, Barbara, he's two years

3:44

old, Like, I will always have a story

3:47

about Jeffrey. And she would say

3:50

her thing was who cares in Wyoming

3:52

or something like that, and I

3:55

was and I would say, Barbara, anybody

3:57

who's a single mom, who is a child cares

4:00

about. Like if I could get

4:02

pregnant right now, See, my ratings would

4:04

go through the roofs. Not to

4:07

mention because I'm at this age where I don't

4:09

even have my uterus anymore, but

4:12

you want to see the goodness of God.

4:14

If I got pregnant now and my ratings,

4:17

I would have jokes for days

4:19

about me. I would love to have a baby right

4:21

now. For this show, they asked me all

4:23

the time, Sherry, are you thinking about fertility

4:26

adoption?

4:27

Oh my god, no, no, but

4:30

it would be great. People love to hear about

4:32

kids. Let me tell you, I'd beat every talk show.

4:34

I'd beat number one having

4:36

kids at this dag on age, I want to be Holder

4:39

take where holda left off? I'm

4:43

older than Holder. I think give

4:46

me a baby girl,

4:49

so or not a divorce?

4:53

Well, listen, I don't think you need much help. The

4:56

show is going so well. You're into three seasons

4:58

now, I feel like just getting

5:00

started.

5:01

Do you do you hope this goes on forever? I

5:04

do.

5:04

I love what I do so much, and I love

5:07

that I'm able to give people a platform,

5:10

you know, to come and talk like I'm going

5:12

through heavy menopause,

5:14

and I think that, you know, I know that that's

5:16

something my audience can relate to.

5:19

I love being able to say to a doctor that

5:21

I follow on social media. Can you please

5:23

come and talk to my audience

5:25

like that, you know, being able to do

5:28

that kind of thing. And I think

5:30

now more than ever, people need laughter.

5:32

Yeah, for sure, for sure.

5:34

I'm so glad you brought that up, though, because I'm

5:37

in whatever is before menopause.

5:39

Premenopause, Harry, menopause, Harry,

5:41

whatever it is, I'm in it. I'm in it. I'm in it.

5:44

Yeah, and I'm

5:46

mad because my girlfriends

5:48

did not prepare me.

5:50

Nobody talks about it. And

5:52

finally one.

5:53

Of them did say something that was

5:55

like, oh, you know, I have this whatever

5:57

it was, and I was like, oh my god, me too, and she goes,

5:59

yeah, this is what it is, and I was like, oh my god, like

6:02

yeah, I wish people talked

6:04

more openly about it, because

6:07

I don't know why we go through this as women, totally

6:09

in the dark, and I have to go on like TikTok to find

6:11

out what's happening to my body exactly.

6:14

I'm ordering everything on Instagram, you

6:16

know, to help the hot flashes.

6:19

And we've had two people on to talk

6:21

about, you're not crazy. This is

6:23

there's seventy signs of

6:26

menopause and perimenopause, and this is what

6:28

you can do.

6:29

I found out from one of the doctors.

6:30

If I eat too much sugar, it like

6:32

I explode with heat. We showed

6:35

a video of a woman who had a hot flash.

6:37

She was bald, steam was coming out

6:39

of her head. Oh it was the

6:41

cold.

6:42

It was cold and you can see the steam and it's

6:44

like our audience appreciates that, and

6:46

I like, girl, my

6:48

tooth came out.

6:50

My tooth came out, it cracked and came.

6:51

I lost my side tooth, and

6:53

I was just like, how the heck dim I lose my side tooth?

6:56

I fly, I brush, And I found out

6:58

that when as we go through menopause and

7:00

lose bone density, so your teeth

7:02

can get loose. All my

7:04

hopes, my dreams, everything my desires

7:07

have went through my side to the air.

7:12

Girl so well.

7:14

I mean, there's so many weird little things, like apparently

7:17

your fingers itching is a sign

7:19

of this perimenopause, and I have very

7:21

itchy fingers, And yes, weird

7:24

stuff with your skin and with

7:27

your hair and your nails, Like we

7:29

should really normalize these conversations.

7:31

I'm so glad you're talking about them.

7:32

Yeah, it's like I love being able to have a show. You know, your

7:34

fingers itch like the palm of my hand. I

7:36

said, either it's an old wife's self. Either

7:38

I'm getting money or I got a rash.

7:40

I don't know.

7:41

What's going on behind

7:44

my knees is itching the back of my arms.

7:46

There is not enough jurgins I can put

7:48

on my body. Oh for whatever

7:50

itchiness is happening. And

7:53

I even asked the lady she came to my show, I

7:55

said, when is the Sex Drive gonna come back?

7:57

That's what I need to know. Yes,

8:00

because this is ridiculous. I'm single.

8:02

This is ridiculous

8:05

because my calling card is I can't get pregnant.

8:08

So hey, I'm gone. I'm

8:10

the one as you won't. I'm the one that you won't.

8:15

Perfection. But it's really

8:17

it's really great to have a talk show

8:19

and.

8:19

See where I can do that and I can have

8:22

fun, and I can have a Linny Kravitz

8:24

come on and I've crushing on him and

8:26

he wants to play with me, so I broke up with him

8:29

on TV.

8:29

I always wanted to do that kind of thing. Yeah,

8:32

it's really fun.

8:33

And I'll tell you I worked at

8:35

a local Fox station in Philadelphia

8:37

this year to shoot an election show, and

8:40

so your show was always on in my office,

8:42

and even though I.

8:43

Know you, it was so fun to

8:46

watch you in your element.

8:47

One of the things I noticed is that you

8:49

don't always go for the obvious joke.

8:51

I can tell you work on your jokes. You'll

8:53

bring up a topic. I think I know where you're going to go

8:56

with it. I think I know where the punchline's going to be,

8:58

but it's you work around you

9:00

go somewhere else, Like how important

9:03

is the joke to you in this talk show?

9:05

Well, it's really important. I want to bring a different kind

9:08

of perspective to it. I'm the only person

9:10

in the talk show space that does a monologue.

9:12

Ellen used to do it, and I loved when

9:14

Ellen did it, and I kind

9:16

of took up that mantle and continued it. So

9:19

I like to go different places where you might

9:21

not think I'm going to go because I think that it's

9:23

boring.

9:24

So I'd like to take it. But that's how it is, you

9:26

know, doing stand up.

9:27

You know, to have a successful stand

9:30

up career, you got to go where you a person doesn't

9:32

think you're going to go. Sure,

9:35

and you know I applied that on

9:37

my show also. I finally, you

9:39

know, we got the budget. They gave me a comedy

9:41

producer who I can say, Okay,

9:44

this is where I'm going. But I've talked about this before.

9:47

Can you think of another way around this that

9:50

we can? You know that we can get to this joke?

9:52

So helpful.

9:53

So it helps to have other wo and their women

9:56

who you know, help me in there. So we

9:58

work an hour.

9:59

Well, I just think in the talk format sometimes

10:02

even if you're coming from comedy, you

10:04

can sort of have this idea that, well, I'm

10:07

just going to go and talk and it's just

10:09

going to be a conversation, and that's part of

10:11

it. But for it to really sing

10:13

and really work and really connect, it has

10:15

to be produced.

10:16

It has to be well.

10:16

Thought out, and you your

10:19

joke construction. It's so obvious

10:22

that you think about it and you're not just sitting

10:24

down and contemplating something for the first time

10:26

in front of your audience.

10:28

You can see.

10:29

I don't mean you can see it like you can see how

10:31

hard you're working, but you can just tell because

10:33

the payoff is so good.

10:34

You know, It's like it takes us an hour

10:37

to come up with fourteen minutes of

10:40

topics. So I absolutely get

10:42

what you're saying. You can see it because I make

10:44

it look effortless, totally very hard

10:46

work.

10:46

I think I worked on something.

10:48

Zoe Kravitz broke up with Channing

10:50

Tatum, and you know, everybody

10:53

knows I like Lenny, so they knew I was going to go there.

10:55

But one of my comedy producers

10:57

said, why.

10:58

Do not you know you called Zoe

11:00

and all you could hear were cries of why

11:03

why that was me? Zoeay's

11:05

fine, that was me, you know and

11:07

I she gave me that joke and I said

11:10

that nobody's gonna expect

11:12

that, you know it, zoeways.

11:13

Fine, that was me. And so it's

11:15

things like that.

11:16

Yeah, I said, throw that, throw that punchline

11:19

in there, because it's great. And

11:21

then I want to talk about what you know, Lenny that

11:23

I wanted to go And so I love

11:25

the I love the art of putting

11:27

it together. Yeah, putting it together. Yeah,

11:30

because I know that the audience if I'm on the floor

11:32

cracking up, I'm like my audience at

11:34

home, who's ironing clothes, are

11:36

cooking, They're gonna love it.

11:38

Totally. No, yeah, totally.

11:40

This this space is not for everyone. I

11:42

don't have to tell you a lot of people have tried it and

11:45

failed. A lot of very smart, talented

11:47

people, yeah, have tried it and failed. So I

11:49

mean you were you were for sure born for this. I want

11:51

to talk about your whole career, but first I

11:53

always like to ask what kind of kid were

11:55

you?

11:56

Wow?

11:57

I was the kid who always got the report

11:59

card that said Sherry is so sweet,

12:02

but she just talks too much. She

12:05

is the class clown. Except

12:07

that was not That was not celebrated

12:10

in my home. You don't come home with a report

12:12

card that said you had a class clown, that you

12:14

talk too much. That was I knew

12:17

I was gonna get a whooping for that. And

12:19

it's so funny because I said to my dad, did

12:22

you ever think I was gonna be making money? He goes, no,

12:24

not at all. But I

12:26

was that girl. I love making people

12:28

happy. I love we had.

12:31

It, and so I was, but I was shy. I

12:33

would.

12:33

I just I love you know, talking at school.

12:36

I love we were put on like variety shows

12:38

for my family and I love making

12:40

them laugh, to see my grandmother smile

12:43

or you know, it just made me happy.

12:46

So I was, you know, I just I like

12:48

people. Yeah.

12:49

And so you grew up in Chicago. You

12:51

have siblings, right, two sisters?

12:54

Were you? Did you feel like you were competing

12:57

for attention of her? Now I got in

12:59

trouble all the time.

13:00

Like my whole family's like, we can't believe that

13:02

this the Sherry is a

13:04

success like this because we thought she would be

13:06

the They thought I would be the one in jail, girl,

13:10

because as I got into my teenage years.

13:11

I was hot too trot.

13:13

Yeah, but uh, you know,

13:15

I did not think it would be What did

13:17

you ask me, girl? When to another menopause

13:19

staying at Foggy Brother, What did you ask

13:21

me?

13:23

Did you feel like you had to compete for attention?

13:26

No, because because I was always I never,

13:29

as a matter of fact, attention found you. Attention

13:31

just found me. Why did you do that? Why?

13:34

I don't know. It just happened.

13:35

Yeah, I have no idea. You have no idea.

13:38

I have no idea.

13:39

Mama, Well

13:42

were you funny? Did you make people laugh? I

13:45

did? I used to my family.

13:47

We used to have, like the Shepherd family would

13:49

have variety shows, and I always won the

13:51

little contest they you

13:53

know, there's they all have stories about

13:55

how it would make them laugh.

13:57

But I just also always I get in trouble

13:59

a lot because I would attention at school.

14:01

I was good, I had good grades, but

14:03

I just wanted to have fun.

14:05

Yeah.

14:06

Yeah, Well, and then your first TV

14:08

gag was a blessing

14:10

and a curse. You you star

14:12

in a sitcom Claig Hornet, Yes,

14:15

and your agent tells you quit your day job

14:17

as a legal secretary because presumablade,

14:20

you're you're gonna be a big star, but the

14:22

show gets canceled and you lose everything.

14:25

Girl, I had no idea how this Hollywood

14:28

thing worked. I auditioned for this show.

14:31

I got it. This is how bad it was.

14:33

The show would send you the check and then you

14:35

cut the commission checks. They sent me

14:37

my first check because I think the first sitcom

14:39

you it was seventy five hundred dollars a week.

14:42

They gave me that check. I taped it to the wall.

14:46

My family didn't teach me nothing about investing

14:48

in stocks and real estate. Like

14:50

I wanted to open up a lemonade stand and my mother

14:53

said it had a whole like thinking we pour,

14:55

oh no, no, you're not gonna no, no,

14:57

no, sir, you're not selling lemonade.

14:59

Half people think we I can't take care of our children.

15:01

Yes, you know, they didn't teach

15:03

me about entrepreneurialship and

15:06

so I didn't know. I'll taped the check up

15:08

to the wall, and my agents

15:10

called and said, did.

15:11

You get paid? And I go, yeah, I keep I'm taping

15:13

the checks up to the wall. That's

15:18

what I did.

15:19

So it was yeah, it was when

15:21

it got canceled. I

15:24

was devastated. I had to move out of my apartment.

15:26

And it wasn't like I had a penan house. I had an apartment. I had a studio

15:28

for three fifty. I was able to move into a one

15:31

bedroom for five fifty a month.

15:33

That same apartment.

15:33

Now, if you go through in Hollywood, it's twenty five

15:36

hundred dollars. I paid five fifty

15:38

and I moved into the Jungle, which is

15:40

the area of La.

15:43

You remember training day with Denzel Washington.

15:45

Yeah, right in there, that's called the Jungle,

15:47

and it was a very bad part of LA

15:50

and I lived over there on my girlfriend's

15:52

couch for almost three years. I

15:54

stayed on the couch and she was a phone sex operator

15:57

and a psychic, so

16:00

that I was okay being

16:02

a psychic because she tell everybody what she wanted to hear. But

16:04

that phone sex operator that messed

16:06

with that.

16:07

I never got sleep. She never she didn't

16:09

try to pull you into either of those businesses.

16:11

No, she didn't, And I couldn't have done it anyway.

16:13

I was like, I came from a real strict

16:15

religion. I was so shy. I couldn't

16:17

do phone sex operating. I

16:19

was gone at nighttime because I was doing stand up,

16:22

But she made her most money at like six in

16:24

the morning and the longing.

16:25

You keep these people on the phone with.

16:27

The wildest fetishes, the great, the nasty

16:29

stuff. That's how you made your money. You had to keep

16:31

them on the phone. You remember all the phone you could get on

16:33

the back of the magazines.

16:34

And she made so much money.

16:37

Well, I always tell people coming up in the news,

16:40

never settle in. Always have a

16:42

few irons in the fire. I have four jobs

16:44

at this moment, because you just never know when

16:47

you know you're gonna lose it, and there

16:49

are lean years in a

16:51

media career. You just have to prepare for them.

16:54

Yeah.

16:55

Absolutely, that is the thing. I've always

16:57

had more than one job. Even with the talk show. People

16:59

think that the talk show ends and I just go home.

17:01

No, I just did a commercial. I represent

17:05

the people. I have my glucose

17:08

monitor on my arm, you know, and

17:10

I represent them. So we had to go film a commercial

17:12

and then I do stand up. I have a comedy tour,

17:15

so I do stand up. I'm working on a children's book,

17:17

you know I do. I come from my family. We're

17:19

hustlers, Like, we don't just sit and

17:22

wait for stuff to come. And I've always

17:25

I've even got on my people. I said,

17:27

you know, this is great that I have this talk show and it's successful.

17:30

But I operate like they could come to me any

17:32

day and go, you know what, right, you

17:35

know we got we got somebody, just somebody.

17:37

Laverne Cox is gonna take your place.

17:39

It just anybody.

17:41

So I always I'm always like, I

17:43

keep up my acting skills. I did a movie over

17:45

the summer with Taraji

17:47

p Henson and Tianna Taylor,

17:50

So I'm like you, and see I always

17:53

have a job.

17:53

It's like you, yeah, because.

17:57

I always have the fear because I've

17:59

worked really hard to get work. Yeah I

18:01

am, you know, And I always have a fear that

18:03

it's going to fall out from under me. And sometimes sometimes

18:05

it has shows come and go, and yeah,

18:08

the environment changes. So I'm always

18:10

paranoid and therefore keeping things

18:13

going. But I find like most successful people

18:15

are hustlers, and even when they get

18:17

to a place where some people would decide to be

18:19

comfortable, the

18:21

hustler does not ever get comfortable.

18:23

Yeah, I never get comfortable even as an actress.

18:26

Do you know me.

18:26

Do you know how many pilots I've

18:29

done, which is they make the first episode

18:31

and try to see if the network will pick it

18:33

up. I've done so many pilots I've

18:35

been.

18:35

On you know.

18:36

I did Suddenly Susan Back with Brickshields

18:38

and Kathy Griffin and the whole

18:40

season.

18:41

I bought a house Girl. It was my very first

18:43

house.

18:44

I said, I'm not sleeping on nobody's couch

18:46

no more. Yeah,

18:48

And I bought a house. I close on

18:50

my house and Brickshields

18:52

came and she goes, yeah, I need to

18:54

talk to you. They're canceling the show. And I

18:57

go, how am I supposed to pay my mortgage? And

18:59

she's like, I don't no, but let me

19:01

tell you. I didn't lose my house. My

19:03

residuals, which is why the actors

19:06

went on strike. My residuals helped

19:08

pay the mortgage. And I started

19:10

doing stand up. I started doing

19:12

guest stars. I went back to work. For

19:14

a moment, I had done Friends.

19:17

I'm Randa, these aren't real. That was my

19:19

biggest line on Friend. The next

19:21

week, I worked at a law firm as

19:24

a legal secretary for I

19:27

was gonna say who's the white guy's wife. They were all white

19:29

on Friends.

19:33

The one who was who had the dark

19:35

hair, he was tall.

19:36

What was his ross? Yeah

19:39

him? His dad is a lawyer,

19:42

okay, and I work with him. And they had a big

19:44

old sign with the friends. You know. They was all

19:46

like hugging each other.

19:47

Yes, And he would bring people by and go, this

19:49

is my secretary. She was on Friends

19:51

and I was miserable. Oh my god, I

19:55

had my bag, lunch and everything.

19:58

I want to talk about that role. I

20:01

love that cameo.

20:03

Ronda, Peta, Peta.

20:06

Hey, Peta, it's

20:08

me Ronza from PS One twenty

20:11

nine.

20:12

I sharedn't my pudding with you, man, I

20:17

gave you my sn't pick man, and you

20:19

act like you don't even know me. I'm

20:21

sure my pudding with you. I share

20:23

my pudding with you, Cherry, Cherry.

20:26

I love that so much.

20:28

When I was watching Friends in

20:30

real time, in real time in the

20:32

nineties, I was like, this is the best cameo

20:34

ever, And now

20:37

watching it back a thousand more times, I'm

20:39

like, it still is.

20:40

It's a Peta Peta and

20:43

thirty Rock my thirty rock stuff.

20:45

Ham Ham Ham,

20:48

You're just oh god, oh

20:52

my God, Ronda,

21:04

there's these lean years.

21:06

They're on the couch. How does the Jamie

21:08

Fox show come along?

21:10

That came at the time I was

21:12

doing Suddenly Susan, and

21:15

they called me in.

21:16

For like just a little

21:18

role to play Garcell

21:21

Bouvet. Who were you know? I

21:23

just make these friends from shows. We're

21:25

dear friends to this day.

21:26

She's now in Real Housewives of Beverly Hills

21:28

and amazing.

21:31

She's so awesome. We still talk.

21:34

She played Jamie's girlfriend and

21:36

she had like a sister circle. I

21:38

was only supposed to come in for one

21:40

or two lines, but I was

21:42

always taking chances, and Jamie

21:45

happened. I knew him from doing stand up, Like Jamie

21:48

stayed with me for a hot

21:50

minute when he had any money.

21:51

But now he had this big show, and.

21:54

I knew that if I

21:56

did something different, because they weren't

21:58

going to ask me back. I put my hand on

22:00

Jamie sty and acted like it

22:02

was the best thing since since

22:05

you know bread, and he took

22:07

my hand off, and I kept doing

22:09

it while he was talking. Then I leaned

22:11

into him and I sniffed his neck and

22:14

it made Jamie laugh. And they kept

22:16

bringing me back to do

22:18

these episodes on the Jamie Fox

22:21

Show. And that's how people would

22:23

bring me back because I would always do something a

22:25

little bit different to catch people's

22:27

attention.

22:28

Yeah, and they liked it.

22:30

Well, that's because I mean, you think about these

22:32

things, you know, and you put

22:34

all of yourself into your work.

22:36

I just I know that about you.

22:38

Tell me about Wendy Williams and

22:40

you going on that show A.

22:41

Light right right?

22:42

Oh gosh, I

22:45

was working on I left,

22:47

I e fired from the View and

22:51

I was doing a Christmas movie and they

22:53

called and they said, we want you

22:55

to because when people were feeling it for Wendy, that's

22:57

when she was in rehab, they were having

22:59

like comedy panels, like a bunch of

23:01

comedians filling in for her, and

23:04

they said, we want you to come and

23:06

be on the comedy panel. And that's

23:08

why I took a chance. And I believed in myself

23:10

and I said, I just came from doing the View like

23:13

that's got a cachet like none

23:15

other. And I said, I don't want

23:17

to be competing with other comics for

23:19

the biggest joke. And I

23:21

said no, And I thought, oh my gosh,

23:23

should I make a mistake, Should I have done

23:25

it, and I said no and stuck

23:27

to my guns, and they said, well, fine,

23:30

we can't use you. But they called me two

23:32

weeks later and they said, okay,

23:34

we'll let you host the show by

23:36

yourself, because that's what I told him. I said, I'm

23:38

not going to do it if I can't host it by myself. After

23:41

coming off the view from it for eight

23:43

years, I don't want to do it. So they said we'll let you host,

23:46

and I said, not only do I want to host by myself,

23:48

I want.

23:48

Two days to fill in for Wendy.

23:51

And I wanted to be Monday and Tuesday

23:53

because all of the big stuff happens over the weekend,

23:56

so the ratings are bigger on a Monday,

23:58

so that you can talk it because

24:01

people try to.

24:01

Bury news over the weekend. You

24:03

know this, of course. So they let

24:06

me do it and it was absolutely

24:09

amazing. It was amazing.

24:11

It was I did it for two days

24:13

and they wanted me to come back, and

24:16

then all of a sudden they called and said, no, you don't have to come

24:18

back. We're going to do reruns. So you know, I

24:20

didn't come back, and that was it.

24:22

They offered me back then a

24:25

talk show deal, but it went

24:27

away, it didn't happen, and I was just.

24:29

Like, oh man, cause I loved it so much.

24:31

So then I went out and tried to pitch my

24:33

own talk show, and that's when everybody

24:36

told me no.

24:37

I mean, I had made

24:39

like a little sizzle reel yep.

24:41

And I said to one lady at a network

24:44

I won't name, Oh my gosh. She was like, I don't

24:46

need to see it, and I said, well, it's only

24:48

like literally three minutes, but it kind

24:50

of will show you what I did when

24:52

I filled in for Wendy and kind of.

24:54

What I envisioned it. She goes, I don't need to see that.

24:57

And at the time, I think Kelly

24:59

Clarkson had her show, and it was another

25:01

woman that had a show and don't remember her name.

25:03

She's like a motivational speaker.

25:05

And they're like, well, maybe we can put you on a show

25:08

with a bunch of chefs.

25:09

And you don't know how to cook, but you learn

25:11

to cook with America.

25:15

That's how you doing these meetings.

25:17

I know, you learn to cook, like

25:19

it's the brightest damn idea,

25:22

right, And I'm looking at this lady going

25:24

I don't cook. I like order door dash or

25:27

like, I don't know how to cook and I don't

25:29

like and she's like, but.

25:31

America would love it. Uh.

25:33

And she basically told me all the reasons why it wouldn't

25:35

work with me. Singular talk

25:37

show host don't typically do well,

25:40

and you know they want younger. And

25:42

I said, but I am a comic, like I

25:45

can make magic where there is none,

25:47

and the silence is where I excel

25:50

at being funny, and I have it on a sizzle

25:52

room and she goes, I don't need to

25:54

see it.

25:55

I think I left that meeting crying.

25:57

Then another person told

25:59

me, you know your

26:01

little how they could tell me I weighed

26:04

too much your little you know, maybe

26:06

slimming down and this.

26:07

Is kind someone said

26:09

that to you within the past couple of years.

26:13

Yeah, so it had to be it was right after

26:15

I left you. So it was around two

26:17

thousand fourteen.

26:19

Oh my god.

26:21

So it wasn't like you're too fat. It

26:23

was cause you have to do they have to colde it.

26:25

It was just like, this is kind of what people

26:27

are looking for a talk

26:29

show and it was no, and

26:32

it was I was devastated. And

26:34

then I went to a network where they were like this.

26:37

This is why I don't I don't believe anybody tell

26:39

us signed to check. The lady was

26:41

like, I don't even need to go to

26:44

anyone.

26:44

You are what America wants.

26:46

I have chills running down

26:48

my arm. I saw you fill in for

26:50

Wendy. We you're gonna

26:52

hear from us. Six weeks later, I

26:55

was like, well, what what's going on? They

26:57

have picked another host that was on the air now. She's

27:00

absolutely amazing, and it

27:02

was devastating. I couldn't stop

27:04

crying because I was like, I've wanted

27:06

this dream for so long and

27:09

everybody's saying no, but it

27:11

comes back around, like you don't let your dream

27:14

die. I put it on the shelf with

27:16

the Fine China, and I hosted

27:18

a game show. I think I might have hosted a It

27:20

was like a littal short lived game show. I did

27:22

more acting, I went on the road and did

27:25

stand up. All of that made it made me

27:27

that much stronger for when they

27:29

offered it to me again and again, so with

27:31

you bring it back to Wendy. They

27:34

wanted me to come in and fill in for her, and

27:37

my ratings were great

27:39

because I was the only one that loved

27:41

doing pop culture like I guess,

27:44

and that was a format that worked

27:46

for her. So I came in and sat in for her,

27:48

and I kept sitting in for her. I

27:51

think even there was a conflict because

27:53

Ellen wanted me to come on her show and

27:55

I hadn't been on her show in twelve years,

27:57

and so it was a big conflict. But it

27:59

worked out, and I

28:02

was an audition nation and they were saying, no, you

28:04

can't go because you're supposed to be here, but they let

28:06

me do it, and so I litterly

28:09

was on there and I said, I know they're going to offer me.

28:11

They're going to offer me.

28:12

So her time was ending, her contract

28:14

was up, so they offered me

28:16

a deal, and her time slot

28:19

was still there. You know when networks, they don't ever

28:21

want to lose the time slot, right because

28:23

if you lose your time slot, you don't get it back.

28:25

They filled it with local programming.

28:28

So her contract was ending and

28:30

I just stepped into that time slot. So

28:33

typically talk shows take a year or two

28:35

to develop. I developed mine in thirty

28:38

days.

28:38

Okay, there's so much I want to get into here. Because you

28:40

just said so many great things.

28:42

I can relate completely

28:44

because I'm in this business too, and I develop as

28:46

well, and I've shopped one thousand

28:49

shows, gotten a thousand

28:51

no's, yeah, also gotten. We love

28:53

this, we can't wait for this, let's do it,

28:56

let's sign a development deal, and then another

28:58

executive comes in and it poof,

29:00

it's gone.

29:01

And it's so exhausting and

29:04

emotional. Yes, and you

29:06

just.

29:07

Got to get used to a lot of rejection. But

29:09

it's hard when you put something, as

29:11

you said, I put it on the shelf. When

29:13

you put it on the shelf, that is agonizing,

29:16

absolutely, because you don't know if it's going to

29:18

come back around. I mean, you just said it comes

29:20

back around, and you hope that it does,

29:24

and it did for you. But

29:26

it's so hard to get through that and keep

29:28

going, Just keep.

29:30

Going, Essie.

29:31

Let me tell you how devastated I was because

29:33

when I say I had to put it on the shelf.

29:35

Yeah, I didn't want to put.

29:36

It on the shelf, but I said, I said, mentally

29:39

and emotionally, heart, my heart

29:42

can't take another no, because

29:44

I knew how I would be different

29:46

from other hosts, and I knew all

29:49

I need is a shot if you can just

29:51

see what I can do, and

29:53

nobody would give me that shot and that was it.

29:55

So I said, I'm just gonna I can't think

29:57

about it anymore because it hurts too

30:00

much. And when I went the show

30:02

Dish Nation, which it takes it's

30:05

a little pop culture show, they called

30:07

and they wanted me to move to Atlanta, and I said,

30:09

I can't move to Atlanta.

30:10

I'm in LA this is where I got to be.

30:12

But I had a meeting with them, the people who do it,

30:14

and in the meeting, this is what I was our

30:17

girl.

30:17

In the meeting.

30:18

My managers they know whenever I'm having

30:20

a meeting, talk to them about a talk

30:23

show for me.

30:23

So they say, we had a great meeting.

30:26

They were like, you know, we're going to do it in LA

30:28

in Atlanta at the same time. And

30:31

so my manager says, well, Sherry's really what she's

30:33

really interested in is a talk

30:35

show. So what can we look

30:37

at in the talk show space girl. They

30:40

said to me, well, you know we already

30:42

have.

30:43

We already have Nick Cannon.

30:45

And when I tell you, I burst into tears,

30:47

not because I was upset at Nick, but when we

30:49

filled in for Wendy the people who had

30:51

who they had a comedy panel, but the

30:53

people who were singular hosts were

30:56

Kiki Palmer, Michael

30:59

Rappaport, Jerry

31:01

O'Connell, Nick Cannon.

31:04

Me. Everybody had

31:06

gotten a deal.

31:06

Jerry O'Connell had a six week test deal,

31:09

Michael Rappaport had like a test deal. Keky

31:12

Palmer went to g M A three with Michael

31:14

Strahan and Sarah Haynes. Everybody

31:17

got a talk show deal except

31:20

me.

31:20

Yeah, like, no, no,

31:23

Jerry had nothing.

31:24

And so when they said they said, well we're doing

31:26

Nick Cannon, his show is supposed to start this

31:29

fall, I burst into tears,

31:31

like and I had to wipe my eyes,

31:33

and I said, oh, I'm sorry I didn't meet

31:35

you know, so happy for Nick. And we came

31:38

downstairs in the parking lot and I started crying

31:40

again and my manager starts

31:42

crying.

31:43

And I go, what are you crying for? But

31:46

what are you crying for? You you get commissioned?

31:49

Why are you?

31:49

And he's like, but I've been with him so long, we're attached

31:52

at the hip, And I said,

31:54

everybody who filled

31:56

in got a chance to

31:58

do it except me. Then

32:01

you start feeling like, well, what is it about me

32:05

that everybody is saying no to? I

32:07

got a great idea, but

32:10

it's sometimes it's a timing thing. See,

32:12

somebody said, I was in church

32:15

and they said, sometimes your dream doesn't

32:17

happen because you got to mature into

32:20

the reality of it. And because

32:22

that if if something happens it's a crash

32:24

and burn, you have to have enough

32:26

up under you said that when you can get

32:28

back up and have the fortitude

32:30

to keep going in the strength. A

32:32

lot of these people on TikTok and social media,

32:34

they get this overnight success, right.

32:37

Unfortunately you're hearing about people.

32:39

Committing suicide, yes, TikTokers,

32:41

and it's overwhelming.

32:43

They don't know how to handle it. They don't know what happens

32:46

when it's too much pressure and or

32:48

when it goes away, or when it goes away.

32:51

We know you and I, Oh, when

32:53

stuff goes away, we know what to do.

32:55

We know exactly how to pivot and go. Okay,

32:57

what we cry or whatever? However we do it?

32:59

What's next? Yeah? Where do I need

33:01

to pivot? Yeah?

33:03

And I think that it

33:06

was a timing thing that you know, and I'm

33:08

very spiritual. God knew

33:10

I couldn't handle this dream in my thirties

33:13

because I'd be out in the street, I'd be a whole.

33:15

I'd be a hole. Who

33:20

want to go out with me? Girl?

33:23

We gonna be sniffing?

33:24

What? Because

33:26

I was out in the streets, Girl, I

33:28

was insecure.

33:30

I'm just telling the truth. Girl.

33:32

You know, my self esteem wasn't

33:34

high. So in my I wanted people

33:37

to like me. I'd have been at parties

33:39

I wasn't supposed to.

33:40

Girl. The FBI would have been like, what party

33:42

was Sherry? Not yet?

33:45

Every time we turn on the damn tape, Cherry

33:47

in the you know. So it

33:50

had to happen at fifty four, where

33:52

I'm more grounded where I want

33:54

to go. You know, I stay at home, but

33:56

I have a lot of life underneath me. Yeah,

33:59

that's when it happened because I've

34:01

had the dream for over twenty years and.

34:03

I get that.

34:04

And I feel the same way looking back at my career

34:06

because I have the opposite of imposter syndrome.

34:09

I think you probably do too.

34:10

Where I don't feel like I'm a fraud,

34:12

I feel like, why aren't you giving me more opportunities?

34:14

Like I know what I can do, and

34:16

I know what I can't do, But I know what I can do. I

34:19

want it always more opportunities, and

34:21

looking back, I'm glad there were things I

34:23

wasn't.

34:23

Ready for ye when I thought I was.

34:26

And I'm glad I'm you know,

34:28

at a point in my career where you

34:30

know, I worked super hard in my twenties so that

34:32

when I got to thirty, I could have a family

34:34

and I could relax a little bit because I had

34:36

done so much. Yeah, and then I'm ramping it up

34:38

again as my son gets older. Like it all worked

34:40

out, But in the middle of it, when you're not

34:43

getting the thing that you know you

34:45

can do, that you know will work,

34:48

it's hard to tell yourself, Oh, the

34:50

timing is just not right.

34:51

It'll come. It's just hard. But I think the biggest

34:53

thing is what we do.

34:55

You got to know how to pivot, Yeah,

34:57

exactly, just kind of keep working

35:00

and pivot and where can I be relevant and

35:02

where can I put my skills to use and look

35:04

for these open doors?

35:05

Can I say one more thing about that?

35:08

A girlfriend told me when I was going

35:10

through the mass devastation of the nose

35:12

for the talk show. She said, Sherry, instead

35:14

of asking for permission

35:17

from them to give you a talk show, why

35:19

don't you start your own. That's

35:21

when I started my podcast Two Funny

35:23

Mamas with my best friend Kim

35:25

Whitley. I said, because this is something

35:27

that we can control, Kim, because she was

35:29

going through her no season. We can

35:32

control it. It was only and then I

35:34

researched it. I got our LLC everything,

35:38

and.

35:38

Then the pandemic hit. I was supposed we supposed to shoot

35:40

it.

35:40

At Kevin Hart, Kevin Hart's

35:42

podcast studio. Jamie Fox wanted

35:44

to produce it.

35:46

COVID hit.

35:46

Oh my god, we had to stay at home, but we put

35:48

it on the air anyway. Yea two

35:51

NAACP Image Awards later.

35:54

Like our fan base is so loyal

35:56

when we have a business we sponsor

35:59

they literally by thousands of

36:01

dollars of whatever because they trust us.

36:04

And that podcast got

36:06

me a development deal with a company.

36:09

They wanted to do a sitcom with me because they went on

36:11

It was one of my rants during COVID of My

36:14

Vagina's Lonely, and I went on a whole

36:16

ramp by like I was sick of

36:18

my son, I'm sick of my dog, I'm

36:21

scared, I'm in this house, my Vagina's

36:23

lonely, and this

36:26

company, the.

36:26

Studio heard it and they gave me a development

36:29

deal.

36:29

It didn't happen because I just the conflict of

36:31

time with my talk show. But I pivoted

36:34

and did something else, and I think that kind

36:37

of opened it up because I wasn't thinking about that talk show.

36:39

I think, no, you're right.

36:41

And I had been asked

36:43

to consult on Aaron

36:46

Sorkin's HBO show

36:48

The Newsroom, and I

36:50

loved that, but that was a very serious

36:52

show about the news. And

36:55

then I got asked to consult on Apple

36:57

TV's The Morning Show, and

37:00

I see all these comedians are going to be in it, you know,

37:02

Reese and Steve Carell and Jennifer Aniston.

37:04

And I'm like, oh, good, this is going to be a comedy about

37:06

my business.

37:07

Great.

37:08

I go to consult writer's room all

37:10

that stuff. It turns into a drama.

37:13

They turn it into a drama.

37:14

So then I'm thinking, gosh, I can't.

37:16

Wait till someone writes

37:18

a comedy about my business and then asks

37:20

me to consult on it. And I'm lying

37:22

in bed one night and I said, well, why don't I just

37:24

write it?

37:25

Why am I.

37:26

Waiting for someone to ask me to consult

37:28

on something they've done?

37:30

I can write it. So I did.

37:31

I wrote the pilot. This is the show that,

37:35

like your talk show, I just really

37:37

really believe in and I still

37:39

do and got all the nose,

37:41

but I wrote it. I got really positive

37:43

feedback, and doing it

37:46

myself, whatever happened

37:48

to it just felt really good because now

37:50

I'm in charge, I'm in control, and we're

37:52

in a business, you and I where everyone

37:54

else is in control of our fate. It feels

37:57

like at all times

38:01

that's hard.

38:02

That is a tough space to live in.

38:03

And when you finally get the agency, like

38:06

you did to say, I don't want to.

38:08

Fill in on the comedy panel. Yeah,

38:10

I want to do two days.

38:11

I want them to be these days and I wanted to When

38:14

you finally get that agency, it's just

38:16

such it's so empowering.

38:18

Yeah, it was. I'm

38:20

thankful. I have a you know, people of

38:22

my team who believe in me. My team.

38:26

I've been together with them ten years, you

38:28

know, and normally you're with agents

38:30

who if you're not bringing in anything, they drop.

38:33

You might have always believed in me,

38:35

and everywhere they went. Talk

38:37

show hosts was on there, yes, you know,

38:40

pushing I got a publish everywhere I go,

38:42

she's going, can we push for chery

38:44

to get a star on the Hollywood Walk of Fame.

38:46

This is what she's like.

38:47

She's never stopped. So I got those

38:49

kind of people, and I'm very very glad, right.

38:52

Can I read your script? Yes?

38:54

What would you mind?

38:56

Because because I love

38:59

that and I love sitcoms, I said,

39:01

I really would love to do a comedy, a single

39:04

camera Yes, comedy different

39:06

from the sitcom of

39:08

a talk show, because the dattlings

39:12

behind the scenes that nobody knows

39:15

about, the the

39:17

things that Barbara Walters used to go

39:19

through with Diane Sawyer because

39:21

there was always everybody knew that, there was

39:24

always that that thing right here because

39:26

they were both trying to get the same guests, the

39:28

stuff that I go through being a

39:30

talk show host, and my other

39:33

compatriots colleagues.

39:35

Yeah, girl, if only

39:37

people knew I feel the same way.

39:38

I just when I get done with this, I want

39:40

to do something like that. Because I used to watch Larry

39:43

the Larry Sanders Larry.

39:45

Sanders Did you

39:48

and I?

39:49

He could only he could only have sex

39:51

when he watched himself on the show. That

39:55

was my favorite episode. I

39:57

just would I would love to read

39:59

it. Well, that's connection,

40:01

That's that's networking.

40:03

Well, I love that absolutely. You can read this absolutely.

40:20

You and I have talked about our sons and

40:22

mental health a bunch.

40:24

Yeah, it's important to both of us.

40:27

And I know Jeffrey is the

40:29

love of your life so much

40:32

like my son is the love of my life.

40:35

And talking about him for me too is important.

40:37

Like you know, he is a huge

40:40

part of me, and I love talking about him. What

40:42

parts of you as a mom

40:45

wanted to explode

40:48

publicly with your love and what parts

40:50

of you as a mom really wanted to protect him

40:52

and keep him, you know private.

40:55

You know. So for me, I've

40:59

always talked about you, Jeffrey.

41:00

I've always talked about from the how

41:02

he was conceived with fertility

41:06

and he's just always

41:08

been a part of my life. So people recognize

41:10

Jeffrey from me bringing him on the view

41:13

and just literally he's nineteen.

41:16

About a year and a half ago, Ssie,

41:19

he said to me because we were at a dunkin Donuts

41:21

and he went the wrong way and I was like, ooh,

41:23

this is gonna be good for the sitting in the chair

41:26

when I talk about Jeffrey, And he looked

41:28

at me and he said, don't talk about me. I'm

41:30

not a story. And

41:32

I guess a teacher at a school laughed and said,

41:34

your mom can make a story out of anything.

41:37

And because my son is on the spectrum,

41:39

he's got it. They used to say Asperger's,

41:41

but they say on the spectrum. So he takes

41:43

everything literal. Yes, my son,

41:46

he does it like nuances and

41:48

things like that sarcasm.

41:51

So he said, I'm not.

41:52

A story, don't talk about me, don't show

41:54

my picture. He's adamant. And

41:57

I broke down and cried and I said, Jeffrey,

42:00

that's my label, Like I'm a mom. Like

42:03

if I don't, I'm not dating anybody. I

42:05

don't go anywhere. You're all I got,

42:07

Like you're my money. Yeah,

42:10

like that's you're all my jokes.

42:12

And

42:14

and now.

42:15

At nineteen, he's going through stuff

42:17

that I want to talk about. That

42:19

is so funny that I know mothers of teenage

42:22

boys go through

42:24

and the angst that they go through and how me

42:26

is and he doesn't.

42:28

Allow me to talk about it.

42:30

It is literally, but I

42:32

have to respect his privacy because Jeffrey

42:34

did not ask for this.

42:35

That's right. I did, that's

42:38

right.

42:38

And I don't want him ever looking

42:40

at something and him being humiliated

42:43

because I talk to other comics and they're like, nope, that's

42:45

how I pay the bills, you know, until

42:47

you move out.

42:48

But I go, no, I have.

42:50

To respect Jeffrey even

42:52

though everything he does every single day

42:55

I want to laugh at and I know other people

42:57

would and I beg him. I go, if I paid

42:59

you for the joke, Jeffrey has no concept of money,

43:02

so that doesn't work. Paying her for the joke,

43:04

me going, Jeffrey, look at how many likes we get.

43:06

What we do?

43:07

You know, little skits together on Instagram

43:10

means nothing to him. I've chosen

43:12

to keep his life private. I'm trying to see if I can

43:14

give Kelly Ripper used to call her son

43:17

the one that shall not have a name, or

43:19

something like, Yeah, if

43:21

I can go my friend's

43:23

son.

43:26

A wink wink, we'll call him Schmefrey.

43:29

We'll call him Schmefrey.

43:31

Yeah. But I gotta respect that.

43:33

So I do keep his life private

43:35

because now people are recognizing him.

43:37

He's a nineteen year old. He's an adult.

43:40

He's an adult, and he deserves

43:42

that. So now I got to get a life. Like I said, I got

43:44

to get pregnant. I need somebody to give me pregnant.

43:46

I need more material.

43:47

I need more material, girl, because

43:50

I can't keep talking about a p dietris cutting my

43:52

bunions open.

43:53

And oh

43:56

my gosh.

43:57

Oh no, So I'm now

43:59

talking about my dates that I go on and you

44:02

know, talk, but I refuse to name anybody.

44:04

Oh oh, why are you seeing people that people

44:06

would know?

44:08

It was a couple. It was a couple of times.

44:10

Yeah, that whole You can't

44:12

tell You can't tell me any of them now that it's over, No.

44:15

Because you'll know, you'll know who it is.

44:17

And it's always it's good, yes, and

44:19

it is some good stories.

44:20

But I'm like, I don't want you know, man,

44:23

I would love to, but but

44:25

they didn't work out. Now it didn't work out. It's

44:27

hard dating. Yeah, one

44:29

was a comic. It's hard dating comics.

44:32

I married one. It was worse.

44:34

It's really hard. It's actors.

44:36

It's really hard. I'll tell you some of the

44:38

stuff that that's telling. One

44:40

actor, he's an actor, he's been in big movies. He

44:43

came to a comedy show that I did. It was great,

44:45

and he I gave him my number. Really

44:48

cute, muscular. And he calls me

44:50

and he's like, I've had crush on you for a long

44:52

time. And I'm like for real and

44:55

and he said he wanted to take me out. I was like, okay,

44:57

absolutely god, and he said, but I have to be honest with

45:00

you. He said, I have a girlfriend.

45:03

As a matter of fact, I have three girlfriends.

45:05

He's into that poly poly

45:08

ammor thing. And I'm

45:10

sitting there on the front. I'm going, so

45:12

you have three and he goes, yes, I have my main

45:15

one and on the weekends, I don't it's

45:17

her weekend. Then I have the other two

45:20

and they don't know about you. They're very, very open.

45:22

And I was like, so you want to you want

45:24

to bring me in what other women?

45:26

And I said I can't. No.

45:28

I'm very glad you're honest with me, but I

45:30

can't get down with that. And he's like, he's

45:33

like, I literally I'm not looking to get

45:35

married, but I know if you're at home

45:37

and you just need somebody to come over, and he said

45:39

all the stuff that he wanted to do to me.

45:41

Oh my god.

45:43

He said, I'm that person and you could call it,

45:45

you know, And I was just like, I hate. As wonderful

45:49

as that sounds, I

45:51

can't.

45:52

I can't do that. No, that would

45:54

not be appealing to me at all.

45:57

So every time I see him in the movie

45:59

every day and he's got his manger, they are always

46:01

he posts her but not the

46:04

other two and.

46:04

She's like, she's really smart

46:06

and she's down with it. Oh, he loves me. Do

46:09

people know that he's got other

46:11

side pieces? No, like the public,

46:14

they don't know. It's amazing.

46:16

I'm telling the stuff that goes on behind

46:19

the scenes. You know.

46:21

It's one that flew me in, flew

46:24

me on this private plane where he

46:26

was going to be.

46:27

I can't.

46:27

I just told you, I can't say the name.

46:30

Flew me in on a private plane. He

46:33

rented out a big, huge mansion

46:35

because he was on comic on

46:37

tour, so rented out a beautiful, beautiful

46:40

place. It was an amazing

46:42

weekend and amazing, but

46:44

it was like, you know, but once just

46:47

the two of us together was amazing. But going

46:49

out now in public, everybody knows who this

46:51

person is. It's yeah, you know,

46:54

I'm kind of walking nine steps behind. And

46:56

it was it just was too much. We

46:59

could even we couldn't make that work.

47:01

So would you want to be with someone

47:04

who's not a celebrity.

47:06

I would like to, but I think it's hard.

47:08

For what's been hard dating

47:11

a regular person is my

47:13

life is so busy. It's

47:16

hard for me to give you the attention that you

47:18

need. It's hard for me. I'm always

47:20

on the road, I'm always I traveled

47:22

twice a month. I'm always it's Jeffrey,

47:25

it's the talk show, it's branding deals,

47:27

it's stand up, it's writing a book. So

47:29

it's a person who's as busy as

47:31

me understands that life,

47:34

right Like the person who flew me in, he

47:37

was so busy. I didn't talk to him again

47:39

for months because he was so

47:41

busy. The actor, the actor that I

47:43

was talking about, he's in another

47:45

country making a movie right now.

47:47

So it's like those

47:49

people understand your life.

47:51

Yeah, And I guess if I didn't work as much, I've

47:53

been with people who were

47:57

I don't want to say regular, but they just do regular,

47:59

typical jobs. And it was always

48:01

like, Sherry, can I walk the red carpet with you?

48:04

Can? Can I? You know?

48:06

I have a script I wanted to write. Could you show

48:08

it to somebody? Or why aren't

48:10

you spending time. Can

48:12

you just spend some time with me? So that's the hard

48:14

thing.

48:15

Yeah, it's easier with people in the business to

48:17

understand your business.

48:18

Yeah, there was a guy who was he was a vice president

48:20

of a corporation and

48:23

he's really busy. But he's like, I

48:25

fly into New York, and when I fly into New York,

48:27

can we go out to dinner? So when

48:29

he flies out, will go out to dinner. There was a chef.

48:32

There was a big, a huge chef.

48:34

It was just like now that one was

48:36

a who you know?

48:40

But he was very, very busy at the time. Chefs

48:43

are great.

48:43

They could is he a TV chef or like a chef chef?

48:46

I'm gonna stop writing. You

48:49

absolutely know him.

48:51

You know him and and you know

48:53

so he would call me when I was on the road and we'd

48:55

be flirting back and forth and it.

48:57

Was almost we were going to meet up. Girl.

48:59

That was like that was too hot to try. I

49:02

was at a restaurant one time. He brought me something he made

49:04

for me, some dessert. You know, Oh,

49:08

I had some good I'm I

49:11

should I have to write a book.

49:13

Yeah.

49:14

At one point about who these maybe

49:17

not give their names with more detail.

49:19

Yeah. Yeah, so I get to I do get

49:21

to have fun.

49:22

And I've learned and now

49:24

at this season, to keep my stuff

49:26

private because I think sometimes so many

49:28

people overshare and then when

49:30

something goes south, you go, oh, please respect

49:33

my privacy and them, you know, on social

49:35

media, it's like.

49:35

Nope, you let us in, you open up the door. We

49:39

want it all.

49:40

That's right, And I don't want I don't want to be making

49:42

no documentaries and how I fell in

49:44

love and I was

49:46

like, j Lo.

49:47

You better stop that girl. This is not

49:49

going to work out. Oh boy, did

49:51

that not work out? I was like, you keep

49:53

your stuff to yourself.

49:54

Stop making documentaries and all

49:56

of this and asking for it.

49:59

Yeah, because too many people in your business. Yeah,

50:02

well she invited them into her business.

50:03

You invite people in and then you can't

50:06

you can't put them out.

50:07

So why now I go, I'm not inviting you in. Yeah,

50:10

Okay, we're gonna do a bit of a lightning round.

50:13

Okay, you've

50:19

already interviewed presidents and first ladies

50:21

and a list actors.

50:22

Who's someone you want to interview but haven't yet? Meryl

50:25

Street? Oh good one.

50:28

I love Meryl Street. So much.

50:29

I want to talk to her about her career. Michelle

50:32

Obama and that

50:35

guy that she's married to can come along.

50:37

I would love to ask him some questions. Yeap. Who

50:40

else I love?

50:41

I just love intelligent people who have

50:43

a sense of humor. Trevor Noah, It's what

50:46

I want. It's been so hard trying to get that man on

50:48

my show. Huh. And

50:51

and I think Jeremy Renner,

50:53

I really want to come on.

50:54

Oh yeah, I've got a story.

50:56

He's got a story, and I love his

50:58

story. And boy,

51:01

I think right now they said it's in the entertainment

51:03

fields a great list.

51:06

Who is the funniest comedian ever? And who's

51:08

the funniest comedian?

51:09

Right now? Who is

51:11

the funniest comedian ever?

51:12

He gets I

51:15

will one of the funniest comedians

51:18

ever.

51:19

I don't know who I could say is one of the funniest.

51:22

I know who I've always loved is Whoopy Goldberg.

51:24

I used to watch her when I was younger, and

51:27

you know, to work with her was it

51:30

was.

51:30

Like a dream.

51:31

She's so talented, so talented,

51:34

And who's one of the funniest now?

51:36

Yeah, I love Oh my.

51:37

Gosh, oh

51:40

you put me on a spot girl because I'm trying to remember

51:43

some of these comics that I know who are so

51:45

funny that I came up with. Chris Rock

51:47

will always be a favorite of mine.

51:49

Yea, Chris Rock.

51:51

And I'm mad at Chris Rock because he's supposed to verify

51:53

me for rayah and

51:55

he has not verified me yet.

51:57

I get on that.

51:58

I'm like in a pending status because you need

52:00

a select you know. You can try to

52:02

get on Ryo, which is the dating site

52:04

for like if you're in the business, but

52:06

they'll put you in and they'll put you into like oh

52:08

you gotta wait. But if you get a celebrity to verify

52:11

you, then you're in.

52:13

And Chris does not need anyone to verify

52:15

you.

52:16

No, yeah, they said I need somebody to verify

52:18

Well maybe not now, but I've

52:20

been on Hole for three years and that's Chris Rock. Yeah,

52:23

that's Chris Rock's fault. So Chris Rock

52:25

will always wander sights. I love there

52:28

and oh my gosh,

52:31

it's so many. Yeah, my

52:34

memory is going because I'm like their comics

52:36

that I love.

52:37

Yeah, that those those

52:40

are good ones. Who's your

52:42

favorite view co host?

52:44

Oh my gosh, my favorite view I

52:47

was like Meredith Via, She's

52:50

just great. She's just easy going and

52:52

cool, no controversy.

52:54

No druma. I love you

52:56

know. I saw the other day Nicole Wallace, Uh

52:58

huh. She didn't know what was me.

53:00

She kind of went past me, and I was I didn't want to be all

53:02

ghetto because we were on the Upper East Side and

53:04

go no.

53:08

She looked like she had come from jogging. So

53:10

I love I.

53:11

Love Nicole Wallace, love

53:14

Joy Behar her mouth. You know, we got

53:16

no more fights, but I spend

53:18

more time with Joy Behart, Lizzie

53:20

Hasselback and our bestess of friends on

53:23

the show because we pray together

53:25

all the time. And but

53:29

I love them all. Whoope has her point of view

53:32

that she brings. I just I got along with all my

53:34

co hosts. Jenny McCarthy was

53:36

so great. She didn't have a good time

53:38

on the show, but she had a good time with me.

53:40

Good good Genie.

53:42

Don't even like talking about the view.

53:45

There was a time literally Jenny and

53:48

I love Jenny because I did a sitcom with Jenny

53:50

a pilot way back when I was

53:52

thirty four years old, and I think Jenny

53:55

was around and we played.

53:55

Horrorse that's literally what we played.

53:57

Like. We played two women who

53:59

slew with everybody, and it was very it

54:01

was very funny, and it didn't make it

54:03

onto Fox. But Jenny would

54:06

not do her homework and they got on my nerves.

54:08

Like I went and saw everybody at the theater

54:11

all the you know, I read the books,

54:13

and so I saw everybody's movie because

54:15

they would have private screenings. And we go

54:17

back in and Barbara would say, dear, did

54:19

you go and see the movie? And Genny would

54:22

go, yeah, Donnie.

54:23

And I we went and it was so ethereal

54:26

and.

54:26

The way they would act, and I was like, bitch, you didn't even

54:28

go. You wasn't even there.

54:30

You and Donnie. I

54:33

was there and I.

54:33

Didn't see y'all nan nowhere

54:36

in no seats. And she and

54:38

Barbara would say good dear, and I was like,

54:40

ooh, I want to call you out so bad because you didn't

54:43

read that book, you didn't go to the theater.

54:46

And so I love

54:49

having We had a lot of fun, but Jenny

54:52

one day, I guess it

54:54

just wasn't working. One day she was wearing glasses

54:56

all the time and like these button

54:59

up shirts.

55:00

So I said why are you dressing

55:02

like that?

55:02

They hadn't made that girl wear glasses so

55:05

she could appear to be And I said, they knew you

55:07

was in Playboy,

55:09

whatever you did, they knew you and

55:11

who you were. And that's

55:14

the behind the scenes of talk show because

55:16

she I was like, what is this with this look

55:19

with the glass? Now you look like a sexy

55:21

school teacher that's trying to flirt

55:23

with your students.

55:24

Is that what they want you to look like? Uh?

55:30

I was Jenny's lifeline on the show.

55:33

When they told us both we weren't coming back, we all

55:35

got drunk.

55:36

It was great. Yeah.

55:40

Okay, you mentioned in Suddenly Susan. You played

55:43

two different characters on Suddenly Susan.

55:46

Who are they?

55:47

I don't know the first character I played because that's

55:49

when I came in as a guest star. Okay,

55:52

so I don't remember. But they called

55:54

me back because Brooke loved me so

55:56

much. They called me back to

55:58

be a series regular, and I played the secretary

56:02

of Eric. Was it

56:04

Miranda or something? It was Miranda.

56:07

It was

56:09

Miranda Charles. I love that role so

56:11

much. I played Eric Idol his

56:14

secretary, and that was one of

56:16

the bright spots of my life. I met Andy

56:18

Dick, who am really good friends with even

56:20

to this day. Well, we went

56:22

through it that needs to be in the show. Well, oh

56:25

my gosh, me and Andy went through. But

56:29

I met Andy Dick and then we

56:31

did a sitcom Less than Perfect, and that's

56:33

when Andy Dick and I became really really

56:35

good friends.

56:36

So a person you played

56:39

on Suddenly Susan was named Ronnie

56:42

Ronnie that's right, Oh my

56:44

gosh. Well, in addition

56:46

to playing Ronda on Friends, where

56:48

else do you play Ronda?

56:52

Oh?

56:52

The Emerald Lagassi Show. No,

56:55

No, I didn't play Ronda on that. Ronda,

56:58

Ronda? Ronda? Else did I play Randa?

57:01

I'll give you a hint. It's a movie.

57:04

It's a movie. It wasn't

57:07

Beauty Shop, was it? No? Oh

57:09

my gosh, it wasn't.

57:12

It wasn't the movie with Kiki Palmer Carlina

57:14

White. No, it was Ronda.

57:17

It wasn't with Alvis Hodge.

57:20

Where else did I play Ronda girl Transformers?

57:24

Well, for first of all,

57:27

my scenes got cut out of transform

57:29

Really Michael Bay.

57:31

I auditioned for Michael Bay

57:34

and he told me to improv, and I improved

57:36

all of my scenes and they put

57:38

me in Transformer two scenes and

57:41

it was Josh Dumal. Dumaal wasn't

57:43

in the movie, huh. He came to it,

57:45

showed my pawn shop. He

57:47

came into my pawn shop and I and I told

57:49

him I wasn't gonna give him no guns unless he took

57:51

his clothes off.

57:53

And it was great, and they cut it out. And

57:55

I tell you why.

57:55

I think they cut out because Michael Bay wanted me to do

57:57

some free stuff for some some deal

58:00

he had and my agents was like, my

58:03

agents like sharing, not coming to help sell

58:05

your telephones. And

58:07

all of a sudden he loved me, Michael Bay, and all

58:09

of a sudden, my scenes were cut out.

58:12

But I'm still I think I was in the credits.

58:14

Yeah, I still get like a little

58:17

check. But my scenes were cut out.

58:19

I think because I told Michael Bay, now, but

58:22

I'll sell your telephones. Now put me in another

58:24

dog on No I will now.

58:27

Okay, we share something in common. We

58:29

both did Celebrity Jeopardy. Who were

58:31

your competitors and how did it go?

58:36

My one competitor was the guy that's

58:38

on Lauren Order SVU.

58:40

He's he's a serious.

58:41

One with Mariska Hargate okay,

58:44

and Chris Maloney. Chris Maloney,

58:46

Chris Maloney, I'm not good with names. And there

58:49

was an other young lady. She's like on ESPN

58:51

and she's really funny, like she

58:54

does com really great. It was

58:56

those two secret to that.

58:58

And you know it's hitting that buzzer. You

59:01

got it. It's all about the buzzer. You got

59:03

to get approved with that buzzer. But also

59:06

they both left with because we

59:08

were all playing for a charity, and

59:10

so my charity.

59:12

I would never see, like you good at

59:14

a Jeopardy.

59:15

I could never Jeopardy is not the lane I swim

59:17

in one hundred thousand dollars pyramid, that's

59:20

the Hollywood Game Night, all

59:22

of those, but Jeopardy.

59:24

I look at it with my grandmother. I huh.

59:26

So they've always asked me.

59:28

I've always said no, but because of the charity,

59:31

I said, yes, no one share

59:33

you walking into death.

59:35

You know you ain't.

59:37

And I said, but I'm doing it for this charity because

59:39

they get I think they gave our charities. Even if

59:41

you lost, you got the charity got thirty thousand dollars.

59:43

Yeah, you can win a million something.

59:45

Lisa and Walter from mamb of Elementary.

59:47

That's her.

59:48

That's her jam. She know a

59:50

lot about nothing. That's

59:52

my girlfriend. She know a lot

59:54

of opinion about a bunch of nothing. So

59:57

when I went in there, when I tell

1:00:00

I thought they was gonna give us easy questions for

1:00:02

the celebrities.

1:00:03

When I tell you them to have questions, they were like in.

1:00:05

Roman eighteen nineteen

1:00:08

forty five, post Jesus,

1:00:10

what was And I was like.

1:00:11

I don't know.

1:00:12

I don't know what that answer is. And then if

1:00:14

I did know it, I couldn't get the buzzer.

1:00:17

So they would say it and I was like, they I

1:00:19

couldn't get the buzzer. And I was like, that's what I was gonna

1:00:21

say. And the girl from ESPN

1:00:23

said, share, you gotta trust your gut and

1:00:25

I go, well.

1:00:26

Hey, bitch, you winning. Now you're telling me to

1:00:28

trust my gut.

1:00:29

Right, So everybody,

1:00:32

I'm telling you sc Chris Maloney

1:00:34

had like sixty four thousand

1:00:37

dollars. The girl from ESPN

1:00:39

had seventy two thousand dollars.

1:00:41

Ask me how much I had about

1:00:44

seven hundred dollars, but

1:00:47

you couldn't tell. I had the most fun

1:00:49

on Celebrity Jeopardy did. They

1:00:52

loved me, and I was so happy.

1:00:54

Rosie O'Donnell even made a post saying why

1:00:56

I should have never did it and I should fire

1:00:58

my team because I look so But I

1:01:00

said, you know what, it wasn't about

1:01:03

me.

1:01:03

That's not why I went on there.

1:01:04

Yeah, I was willing to make myself look crazy

1:01:06

because my charity got thirty thousand and

1:01:09

every time they run that show, people

1:01:11

donate to her chair her organization.

1:01:15

Like people have put her in the will.

1:01:16

They're like, when I die, I want five

1:01:18

thousand a month to come to you. She's made

1:01:21

so much money from me looking

1:01:23

silly.

1:01:23

I didn't take myself seriously. Yeah.

1:01:26

Yeah, it's a tough show to do

1:01:28

though, it's how did you do well?

1:01:31

Sherry? I won, but I see,

1:01:33

I know it. That's why I said that. That's something

1:01:35

you came.

1:01:36

Down to the wager at the end, and you

1:01:39

know, it really could have gone either way.

1:01:41

And I was on with some very smart people, but you.

1:01:43

Know it was I was very nervous because you can

1:01:45

get very embarrassed coming

1:01:48

into that, coming into that show, but it went okay.

1:01:50

No to self when they call me back for Celebrity Jeopardy,

1:01:52

because they will they're going because I was so,

1:01:55

I was the entertainment of the show, and

1:01:57

I'm gonna tell them in my contract. Sea

1:02:00

Cup is not to be on the same platform

1:02:03

with me. Sea Cup can

1:02:05

come on Wheel of Fortune because I'm a I'm a

1:02:07

dominate you definitely be me.

1:02:09

That's my dag on show Wheel of Fortune. I get

1:02:11

I get to that, I get to that left at Sea Cup

1:02:14

can come on Hollywood Gag Night. At Sea Cup can

1:02:16

try to beat me one hundred thousand dollars Pyramid.

1:02:18

I will run you into the ground. I

1:02:20

get my people to the Winter Circle.

1:02:23

Okay that, Jeffardy, You're not

1:02:25

gonna be on that with me.

1:02:26

Girl, don't worry.

1:02:29

Okay.

1:02:29

The final question is the most important

1:02:31

to me culturally.

1:02:34

Okay, when is iced coffee

1:02:36

season?

1:02:38

I don't know because I drink jasmin tea. Okay,

1:02:42

I don't drink I don't drink coffee. I do

1:02:44

mushroom coffee and I do green

1:02:46

I do jazzmine tea.

1:02:48

If you were to drink iced coffee, when

1:02:51

would the season be? It would

1:02:53

have to be like around now.

1:02:55

Well, no, it have to be when it's hot, right

1:02:58

like around the spring.

1:02:59

No, in the spring summer.

1:03:00

I would think ice coffee in

1:03:02

the spring or the summer would be great. Why

1:03:04

on earth would you drink an ice coffee now?

1:03:07

Unless you like me? You hot flash,

1:03:09

so that would absolutely I'm gonna

1:03:11

change my answer to be dead of

1:03:13

winter because that's when I'm hot flashing the most.

1:03:17

The correct answer is you're round, the correct you're

1:03:19

round, You're round.

1:03:20

Okay, it's always ice coffee season.

1:03:23

But as a non iced coffee drinker, you're

1:03:25

at a disadvantage.

1:03:27

So I won't hold that against you.

1:03:28

So you pulling celebrity Jeopardy on me right now.

1:03:30

That's why you're not gonna play with me. Why

1:03:33

you're not gonna play with me?

1:03:34

That was unfair. How you be shady without

1:03:36

being shady? There you go. Well,

1:03:40

Sherry, I love you and I'm so glad you

1:03:42

did this. Thank you so much. Gosh,

1:03:44

it was so much fun.

1:03:45

Thank you so fun. And I just love

1:03:47

watching you and all of your success.

1:03:50

You deserve it.

1:03:50

Well, you have to come play with me, please, and I want to see

1:03:52

your script. You have to come play with me on the couch, okay,

1:03:55

perfect, And I need to read your script like me

1:03:57

terrific?

1:03:58

All right, all right, thank you, oh girl.

1:04:02

Coming up on Off the Cup next week, I sit

1:04:05

down with Stephen Weber, star

1:04:07

of the nineties sitcom

1:04:09

Wings.

1:04:11

How does the role of Brian Hackett

1:04:13

come to you? Good

1:04:16

segue?

1:04:18

Well, I mean that was first of all, I

1:04:21

was that guy in many respects.

1:04:23

I was kind of a snarky,

1:04:26

affable dickhead.

1:04:31

Off the Cup is a production of iHeart Podcasts

1:04:33

as part of the Recent Choice network.

1:04:35

I'm your Host SI Cup.

1:04:37

Editing and sound designed by Derek Clements. Our

1:04:39

executive producers are Mesie Cup, Lauren

1:04:41

Hanson, and Lindsay Hoffman. If

1:04:43

you like Off the Cup, please rate and review

1:04:45

wherever you get your podcasts, follow,

1:04:47

or subscribe for new episodes every Wednesday.