Sherri Shepherd isn't asking for permission

This week, it's the hilarious and talented Sherri Shepherd! The comedian talks to S.E. about those touch-and-go early days, jumping from sitcom to sitcom hoping one would take off, as well as her most indelible cameos (remember Rhonda from Friends?). The two also bond over the rejections they've weathered in this mercurial media and entertainment business and share strategies for thick skins and flexibility. And Sherri shares what it took to finally fulfill her dream, to solo-host her own daytime talk show, Sherri, and where she's finding material these days.

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Episode Transcript

Speaker 1 (00:01):
She basically told me all the reasons why it wouldn't
work with me. Singular talk show host don't typically do well,
and you know they want younger, And I said, but
I am a comic like I can make magic where
there is none.

Speaker 2 (00:16):
Welcome to off the cup my personal anti anxiety antidote.
As many of you know, I've had a varied media
career where I've been able to play in a number
of sandboxes, and one of them was The View. I
have a relationship with a View that is mixed, mixed,
we'll say mixed. I have some wonderful memories of guest

(00:38):
hosting the View and in fact auditioning to be a
permanent host on the View. And I have some terrible
memories of guest hosting the View and auditioning to be
on the View.

Speaker 3 (00:47):
It's not always a fun place to be.

Speaker 2 (00:49):
But I have to say today's guest is one of
the bright spots for me over the many times that
I did it. She was always so kind, so genuine,
so warm, so embracing lifting She's also one of the
funniest people I know. She can make me laugh when
I least expect it, and in a way that I'm
not expecting it, and I know that's why people love

(01:09):
watching her every day now, and I'm so glad they
get to. She's an actress, a comedian, and author, a podcaster,
the Emmy Award winning future Hollywood Walk of Fame Star
winner for the Class of twenty twenty five Daytime's Funniest
host Sherry Shephard, Welcome to Off the Cup.

Speaker 1 (01:26):
Oh, I'm so glad to be here. We've been trying
to get this hook this up for the longest.

Speaker 2 (01:30):
It's a it's been a busy year, but I'm so
glad we finally got this. Got me on the books.
I just adore you. And you know what I mean
about the view. You know what I'm talking about.

Speaker 3 (01:40):
Oh, absolutely, I understand. You know, you come on there and.

Speaker 1 (01:43):
As a guest host, it's a whole different vibe and
you're you know, you got these women who have their
own they get the thing, and you're coming in with
a different opinion. Yeah, and trying to be heard. Yeah,
it's it's you know, it's a lot.

Speaker 2 (01:57):
It's a lot, and I don't want to tell horror
story is I have them. But I also just I
just love getting to work with nice women like you.
I'll focus on the positive you. Jenny McCarthy was always
so great.

Speaker 3 (02:10):
I had organ too.

Speaker 2 (02:11):
But can I just say, I'm so glad you got
out and got your own spot because you deserve it.

Speaker 3 (02:18):
Thank you, and you are so at home on the
Scherry Show. It's for me.

Speaker 2 (02:24):
It feels like it's one hundred percent you were meant
to do. Yeah, do you feel that way right now?
Like I am where I.

Speaker 3 (02:29):
Need to be. I am where I need to be,
and this is what for me.

Speaker 1 (02:34):
I've always wanted my own talk show, so this is
what I envision what I am doing right now now.

Speaker 3 (02:39):
The View was a great.

Speaker 1 (02:40):
Platform for me. Barbara Walters was a wonderful mentor who
helped me find my voice so that I could, you know,
take that over here to my show and you know,
they all the ladies were great and that was a
great experience.

Speaker 3 (02:55):
But this is for Sherry.

Speaker 1 (02:58):
That was I was just I was one of many posts,
you know, for that season.

Speaker 3 (03:04):
That's seven years all you. This is all me you,
and what I love is it's all of you.

Speaker 2 (03:10):
It's your funny side, which obviously you lead with because
you're so funny you, but it's your heart.

Speaker 3 (03:18):
It's your family.

Speaker 2 (03:19):
It's all the things about you that you get to
do on this show.

Speaker 1 (03:23):
It's so funny because when I do the view, I
would always have a story about.

Speaker 3 (03:27):
My son Jeffrey.

Speaker 1 (03:28):
I did it from the time he was two years
old up until he was about ten, I think, and
I always.

Speaker 3 (03:34):
Had a story.

Speaker 1 (03:35):
And I remember Barbara Walter said to me one day
when another Jeffrey story, and I said, Barbara, he's two
years old, Like, I will always have a story about Jeffrey.
And she would say her thing was who cares in
Wyoming or something like that, and I was and I

(03:55):
would say, Barbara, anybody who's a single mom, who is
a child cares about. Like if I could get pregnant
right now, See, my ratings would go through the roofs.
Not to mention because I'm at this age where I
don't even have my uterus anymore, but you want to
see the goodness of God. If I got pregnant now

(04:16):
and my ratings, I would have jokes for days about me.
I would love to have a baby right now. For
this show, they asked me all the time, Sherry, are
you thinking about fertility adoption?

Speaker 3 (04:27):
Oh my god, no, no, but it would be great.
People love to hear about kids. Let me tell you,
I'd beat every talk show.

Speaker 1 (04:34):
I'd beat number one having kids at this dag on age,
I want to be Holder take where holda left off?
I'm older than Holder. I think give me a baby girl,
so or not a divorce?

Speaker 2 (04:53):
Well, listen, I don't think you need much help. The
show is going so well. You're into three seasons now,
I feel like just getting started.

Speaker 3 (05:01):
Do you do you hope this goes on forever? I do.

Speaker 1 (05:04):
I love what I do so much, and I love
that I'm able to give people a platform, you know,
to come and talk like I'm going through heavy menopause,
and I think that, you know, I know that that's
something my audience can relate to. I love being able
to say to a doctor that I follow on social media.
Can you please come and talk to my audience like that,

(05:26):
you know, being able to do that kind of thing.
And I think now more than ever, people need laughter.

Speaker 3 (05:32):
Yeah, for sure, for sure.

Speaker 2 (05:34):
I'm so glad you brought that up, though, because I'm
in whatever is before menopause.

Speaker 3 (05:39):
Premenopause, Harry, menopause, Harry, whatever it is, I'm in it.
I'm in it. I'm in it.

Speaker 2 (05:44):
Yeah, and I'm mad because my girlfriends did not prepare me.

Speaker 3 (05:50):
Nobody talks about it. And finally one.

Speaker 2 (05:53):
Of them did say something that was like, oh, you know,
I have this whatever it was, and I was like,
oh my god, me too, and she goes, yeah, this
is what it is, and I was like, oh my god,
like yeah, I wish people talked more openly about it,
because I don't know why we go through this as women,
totally in the dark, and I have to go on
like TikTok to find out what's happening to my body exactly.

Speaker 1 (06:14):
I'm ordering everything on Instagram, you know, to help the
hot flashes. And we've had two people on to talk about,
you're not crazy. This is there's seventy signs of menopause
and perimenopause, and this is what you can do.

Speaker 3 (06:29):
I found out from one of the doctors.

Speaker 1 (06:30):
If I eat too much sugar, it like I explode
with heat. We showed a video of a woman who
had a hot flash.

Speaker 3 (06:37):
She was bald, steam was coming out of her head.
Oh it was the cold.

Speaker 1 (06:42):
It was cold and you can see the steam and
it's like our audience appreciates that, and I like, girl,
my tooth came out.

Speaker 3 (06:50):
My tooth came out, it cracked and came.

Speaker 1 (06:51):
I lost my side tooth, and I was just like,
how the heck dim I lose my side tooth? I fly,
I brush, And I found out that when as we
go through menopause and lose bone density, so your teeth
can get loose. All my hopes, my dreams, everything my
desires have went through my side to the air.

Speaker 3 (07:12):
Girl so well.

Speaker 2 (07:14):
I mean, there's so many weird little things, like apparently
your fingers itching is a sign of this perimenopause, and
I have very itchy fingers, And yes, weird stuff with
your skin and with your hair and your nails, Like
we should really normalize these conversations.

Speaker 3 (07:31):
I'm so glad you're talking about them.

Speaker 1 (07:32):
Yeah, it's like I love being able to have a show.
You know, your fingers itch like the palm of my hand.
I said, either it's an old wife's self. Either I'm
getting money or I got a rash.

Speaker 3 (07:40):
I don't know.

Speaker 1 (07:41):
What's going on behind my knees is itching the back
of my arms. There is not enough jurgins I can
put on my body. Oh for whatever itchiness is happening.
And I even asked the lady she came to my show,
I said, when is the Sex Drive gonna come back?

Speaker 3 (07:57):
That's what I need to know. Yes, because this is ridiculous.
I'm single. This is ridiculous because my calling card is
I can't get pregnant. So hey, I'm gone. I'm the
one as you won't. I'm the one that you won't. Perfection.
But it's really it's really great to have a talk

(08:19):
show and.

Speaker 1 (08:19):
See where I can do that and I can have fun,
and I can have a Linny Kravitz come on and
I've crushing on him and he wants to play with me,
so I broke up with him on TV.

Speaker 3 (08:29):
I always wanted to do that kind of thing. Yeah,
it's really fun.

Speaker 2 (08:33):
And I'll tell you I worked at a local Fox
station in Philadelphia this year to shoot an election show,
and so your show was always on in my office,
and even though I.

Speaker 3 (08:43):
Know you, it was so fun to watch you in
your element.

Speaker 2 (08:47):
One of the things I noticed is that you don't
always go for the obvious joke. I can tell you
work on your jokes. You'll bring up a topic. I
think I know where you're going to go with it.
I think I know where the punchline's going to be,
but it's you work around you go somewhere else, Like
how important is the joke to you in this talk show?

Speaker 1 (09:05):
Well, it's really important. I want to bring a different
kind of perspective to it. I'm the only person in
the talk show space that does a monologue. Ellen used
to do it, and I loved when Ellen did it,
and I kind of took up that mantle and continued it.
So I like to go different places where you might
not think I'm going to go because I think that
it's boring.

Speaker 3 (09:24):
So I'd like to take it. But that's how it is,
you know, doing stand up.

Speaker 1 (09:27):
You know, to have a successful stand up career, you
got to go where you a person doesn't think you're
going to go. Sure, and you know I applied that
on my show also. I finally, you know, we got
the budget. They gave me a comedy producer who I
can say, Okay, this is where I'm going. But I've
talked about this before. Can you think of another way

(09:48):
around this that we can? You know that we can
get to this joke?

Speaker 3 (09:52):
So helpful.

Speaker 1 (09:53):
So it helps to have other wo and their women
who you know, help me in there. So we work
an hour.

Speaker 2 (09:59):
Well, I just think in the talk format sometimes even
if you're coming from comedy, you can sort of have
this idea that, well, I'm just going to go and
talk and it's just going to be a conversation, and
that's part of it. But for it to really sing
and really work and really connect, it has to be produced.

Speaker 3 (10:16):
It has to be well.

Speaker 2 (10:16):
Thought out, and you your joke construction. It's so obvious
that you think about it and you're not just sitting
down and contemplating something for the first time in front
of your audience.

Speaker 3 (10:28):
You can see.

Speaker 2 (10:29):
I don't mean you can see it like you can
see how hard you're working, but you can just tell
because the payoff is so good.

Speaker 1 (10:34):
You know, It's like it takes us an hour to
come up with fourteen minutes of topics. So I absolutely
get what you're saying. You can see it because I
make it look effortless, totally very hard work.

Speaker 3 (10:46):
I think I worked on something.

Speaker 1 (10:48):
Zoe Kravitz broke up with Channing Tatum, and you know,
everybody knows I like Lenny, so they knew I was
going to go there.

Speaker 3 (10:55):
But one of my comedy producers said, why.

Speaker 1 (10:58):
Do not you know you called Zoe and all you
could hear were cries of why why that was me?
Zoeay's fine, that was me, you know and I she
gave me that joke and I said that nobody's gonna
expect that, you know it, zoeways.

Speaker 3 (11:13):
Fine, that was me. And so it's things like that.

Speaker 1 (11:16):
Yeah, I said, throw that, throw that punchline in there,
because it's great. And then I want to talk about
what you know, Lenny that I wanted to go And
so I love the I love the art of putting
it together. Yeah, putting it together. Yeah, because I know
that the audience if I'm on the floor cracking up,
I'm like my audience at home, who's ironing clothes, are cooking,

(11:37):
They're gonna love it.

Speaker 3 (11:38):
Totally. No, yeah, totally.

Speaker 2 (11:40):
This this space is not for everyone. I don't have
to tell you a lot of people have tried it
and failed. A lot of very smart, talented people, yeah,
have tried it and failed. So I mean you were
you were for sure born for this. I want to
talk about your whole career, but first I always like
to ask what kind of kid were you?

Speaker 3 (11:56):
Wow?

Speaker 1 (11:57):
I was the kid who always got the report card
that said Sherry is so sweet, but she just talks
too much. She is the class clown. Except that was
not That was not celebrated in my home. You don't
come home with a report card that said you had
a class clown, that you talk too much. That was
I knew I was gonna get a whooping for that.

(12:19):
And it's so funny because I said to my dad,
did you ever think I was gonna be making money?
He goes, no, not at all. But I was that girl.
I love making people happy. I love we had.

Speaker 3 (12:31):
It, and so I was, but I was shy. I would.

Speaker 1 (12:33):
I just I love you know, talking at school. I
love we were put on like variety shows for my
family and I love making them laugh, to see my
grandmother smile or you know, it just made me happy.

Speaker 3 (12:46):
So I was, you know, I just I like people. Yeah.

Speaker 2 (12:49):
And so you grew up in Chicago. You have siblings, right,
two sisters?

Speaker 3 (12:54):
Were you? Did you feel like you were competing for
attention of her? Now I got in trouble all the time.

Speaker 1 (13:00):
Like my whole family's like, we can't believe that this
the Sherry is a success like this because we thought
she would be the They thought I would be the
one in jail, girl, because as I got into my
teenage years.

Speaker 3 (13:11):
I was hot too trot.

Speaker 1 (13:13):
Yeah, but uh, you know, I did not think it
would be What did you ask me, girl? When to
another menopause staying at Foggy Brother, What did you ask me?

Speaker 3 (13:23):
Did you feel like you had to compete for attention? No,
because because I was always I never, as a matter
of fact, attention found you. Attention just found me. Why
did you do that? Why? I don't know. It just happened.

Speaker 1 (13:35):
Yeah, I have no idea. You have no idea. I
have no idea.

Speaker 3 (13:39):
Mama, Well were you funny? Did you make people laugh?
I did? I used to my family.

Speaker 1 (13:47):
We used to have, like the Shepherd family would have
variety shows, and I always won the little contest they
you know, there's they all have stories about how it
would make them laugh.

Speaker 3 (13:57):
But I just also always I get in trouble a
lot because I would attention at school.

Speaker 1 (14:01):
I was good, I had good grades, but I just
wanted to have fun.

Speaker 3 (14:05):
Yeah.

Speaker 2 (14:06):
Yeah, Well, and then your first TV gag was a
blessing and a curse. You you star in a sitcom
Claig Hornet, Yes, and your agent tells you quit your
day job as a legal secretary because presumablade, you're you're
gonna be a big star, but the show gets canceled
and you lose everything.

Speaker 1 (14:25):
Girl, I had no idea how this Hollywood thing worked.
I auditioned for this show.

Speaker 3 (14:31):
I got it. This is how bad it was.

Speaker 1 (14:33):
The show would send you the check and then you
cut the commission checks. They sent me my first check
because I think the first sitcom you it was seventy
five hundred dollars a week. They gave me that check.
I taped it to the wall. My family didn't teach
me nothing about investing in stocks and real estate. Like
I wanted to open up a lemonade stand and my
mother said it had a whole like thinking we pour,

(14:55):
oh no, no, you're not gonna no, no, no, sir,
you're not selling lemonade.

Speaker 3 (14:59):
Half people think we I can't take care of our children.

Speaker 1 (15:01):
Yes, you know, they didn't teach me about entrepreneurialship and
so I didn't know. I'll taped the check up to
the wall, and my agents called and said, did.

Speaker 3 (15:11):
You get paid? And I go, yeah, I keep I'm
taping the checks up to the wall. That's what I did.

Speaker 1 (15:19):
So it was yeah, it was when it got canceled.
I was devastated. I had to move out of my apartment.
And it wasn't like I had a penan house. I
had an apartment. I had a studio for three fifty.
I was able to move into a one bedroom for
five fifty a month.

Speaker 3 (15:33):
That same apartment.

Speaker 1 (15:33):
Now, if you go through in Hollywood, it's twenty five
hundred dollars. I paid five fifty and I moved into
the Jungle, which is the area of La.

Speaker 3 (15:43):
You remember training day with Denzel Washington.

Speaker 1 (15:45):
Yeah, right in there, that's called the Jungle, and it
was a very bad part of LA and I lived
over there on my girlfriend's couch for almost three years.
I stayed on the couch and she was a phone
sex operator and a psychic, so that I was okay
being a psychic because she tell everybody what she wanted
to hear. But that phone sex operator that messed with that.

Speaker 3 (16:07):
I never got sleep. She never she didn't try to
pull you into either of those businesses.

Speaker 1 (16:11):
No, she didn't, And I couldn't have done it anyway.
I was like, I came from a real strict religion.
I was so shy. I couldn't do phone sex operating.
I was gone at nighttime because I was doing stand up,
But she made her most money at like six in
the morning and the longing.

Speaker 3 (16:25):
You keep these people on the phone with.

Speaker 1 (16:27):
The wildest fetishes, the great, the nasty stuff. That's how
you made your money. You had to keep them on
the phone. You remember all the phone you could get
on the back of the magazines.

Speaker 3 (16:34):
And she made so much money.

Speaker 2 (16:37):
Well, I always tell people coming up in the news,
never settle in. Always have a few irons in the fire.
I have four jobs at this moment, because you just
never know when you know you're gonna lose it, and
there are lean years in a media career. You just
have to prepare for them.

Speaker 3 (16:54):
Yeah.

Speaker 1 (16:55):
Absolutely, that is the thing. I've always had more than
one job. Even with the talk show. People think that
the talk show ends and I just go home. No,
I just did a commercial. I represent the people. I
have my glucose monitor on my arm, you know, and
I represent them. So we had to go film a
commercial and then I do stand up. I have a
comedy tour, so I do stand up. I'm working on

(17:16):
a children's book, you know I do. I come from
my family. We're hustlers, Like, we don't just sit and
wait for stuff to come. And I've always I've even
got on my people. I said, you know, this is
great that I have this talk show and it's successful.
But I operate like they could come to me any
day and go, you know what, right, you know we
got we got somebody, just somebody. Laverne Cox is gonna

(17:38):
take your place.

Speaker 3 (17:39):
It just anybody.

Speaker 1 (17:41):
So I always I'm always like, I keep up my
acting skills. I did a movie over the summer with
Taraji p Henson and Tianna Taylor, So I'm like you,
and see I always have a job.

Speaker 3 (17:53):
It's like you, yeah, because.

Speaker 2 (17:57):
I always have the fear because I've worked really hard
to get work. Yeah I am, you know, And I
always have a fear that it's going to fall out
from under me. And sometimes sometimes it has shows come
and go, and yeah, the environment changes. So I'm always
paranoid and therefore keeping things going. But I find like
most successful people are hustlers, and even when they get

(18:17):
to a place where some people would decide to be comfortable,
the hustler does not ever get comfortable.

Speaker 3 (18:23):
Yeah, I never get comfortable even as an actress. Do
you know me.

Speaker 1 (18:26):
Do you know how many pilots I've done, which is
they make the first episode and try to see if
the network will pick it up. I've done so many
pilots I've been.

Speaker 3 (18:35):
On you know.

Speaker 1 (18:36):
I did Suddenly Susan Back with Brickshields and Kathy Griffin
and the whole season.

Speaker 3 (18:41):
I bought a house Girl. It was my very first house.

Speaker 1 (18:44):
I said, I'm not sleeping on nobody's couch no more. Yeah,
And I bought a house. I close on my house
and Brickshields came and she goes, yeah, I need to
talk to you. They're canceling the show. And I go,
how am I supposed to pay my mortgage? And she's like,
I don't no, but let me tell you. I didn't
lose my house. My residuals, which is why the actors

(19:06):
went on strike. My residuals helped pay the mortgage. And
I started doing stand up. I started doing guest stars.
I went back to work. For a moment, I had
done Friends. I'm Randa, these aren't real. That was my
biggest line on Friend. The next week, I worked at
a law firm as a legal secretary for I was

(19:27):
gonna say who's the white guy's wife. They were all
white on Friends. The one who was who had the
dark hair, he was tall.

Speaker 3 (19:36):
What was his ross? Yeah him? His dad is a lawyer, okay,
and I work with him. And they had a big
old sign with the friends. You know. They was all
like hugging each other.

Speaker 1 (19:47):
Yes, And he would bring people by and go, this
is my secretary. She was on Friends and I was miserable.
Oh my god, I had my bag, lunch and everything.

Speaker 3 (19:58):
I want to talk about that role. I love that cameo. Ronda, Peta, Peta.

Speaker 1 (20:06):
Hey, Peta, it's me Ronza from PS One twenty nine.

Speaker 3 (20:12):
I sharedn't my pudding with you, man, I gave you
my sn't pick man, and you act like you don't
even know me. I'm sure my pudding with you. I
share my pudding with you, Cherry, Cherry. I love that
so much.

Speaker 2 (20:28):
When I was watching Friends in real time, in real
time in the nineties, I was like, this is the
best cameo ever, And now watching it back a thousand
more times, I'm like, it still is.

Speaker 1 (20:40):
It's a Peta Peta and thirty Rock my thirty rock stuff.

Speaker 4 (20:45):
Ham Ham Ham, You're just oh god, oh my God, Ronda,
there's these lean years.

Speaker 3 (21:06):
They're on the couch. How does the Jamie Fox show
come along?

Speaker 1 (21:10):
That came at the time I was doing Suddenly Susan,
and they called me in.

Speaker 3 (21:16):
For like just a little role to play Garcell Bouvet.
Who were you know? I just make these friends from shows.
We're dear friends to this day.

Speaker 1 (21:26):
She's now in Real Housewives of Beverly Hills and amazing.

Speaker 3 (21:31):
She's so awesome. We still talk.

Speaker 1 (21:34):
She played Jamie's girlfriend and she had like a sister circle.
I was only supposed to come in for one or
two lines, but I was always taking chances, and Jamie happened.
I knew him from doing stand up, Like Jamie stayed
with me for a hot minute when he had any money.

Speaker 3 (21:51):
But now he had this big show, and.

Speaker 1 (21:54):
I knew that if I did something different, because they
weren't going to ask me back. I put my hand
on Jamie sty and acted like it was the best
thing since since you know bread, and he took my
hand off, and I kept doing it while he was talking.
Then I leaned into him and I sniffed his neck
and it made Jamie laugh. And they kept bringing me

(22:17):
back to do these episodes on the Jamie Fox Show.
And that's how people would bring me back because I
would always do something a little bit different to catch
people's attention.

Speaker 3 (22:28):
Yeah, and they liked it.

Speaker 2 (22:30):
Well, that's because I mean, you think about these things,
you know, and you put all of yourself into your work.

Speaker 3 (22:36):
I just I know that about you.

Speaker 2 (22:38):
Tell me about Wendy Williams and you going on that
show A.

Speaker 3 (22:41):
Light right right?

Speaker 1 (22:42):
Oh gosh, I was working on I left, I e
fired from the View and I was doing a Christmas
movie and they called and they said, we want you
to because when people were feeling it for Wendy, that's
when she was in rehab, they were having like comedy panels,
like a bunch of comedians filling in for her, and

(23:04):
they said, we want you to come and be on
the comedy panel. And that's why I took a chance.
And I believed in myself and I said, I just
came from doing the View like that's got a cachet
like none other. And I said, I don't want to
be competing with other comics for the biggest joke. And
I said no, And I thought, oh my gosh, should
I make a mistake, Should I have done it, and

(23:26):
I said no and stuck to my guns, and they said, well, fine,
we can't use you. But they called me two weeks
later and they said, okay, we'll let you host the
show by yourself, because that's what I told him. I said,
I'm not going to do it if I can't host
it by myself. After coming off the view from it
for eight years, I don't want to do it. So
they said we'll let you host, and I said, not

(23:47):
only do I want to host by myself, I want.

Speaker 3 (23:48):
Two days to fill in for Wendy.

Speaker 1 (23:51):
And I wanted to be Monday and Tuesday because all
of the big stuff happens over the weekend, so the
ratings are bigger on a Monday, so that you can
talk it because people try to.

Speaker 3 (24:01):
Bury news over the weekend. You know this, of course.
So they let me do it and it was absolutely amazing.
It was amazing.

Speaker 1 (24:11):
It was I did it for two days and they
wanted me to come back, and then all of a
sudden they called and said, no, you don't have to
come back. We're going to do reruns. So you know,
I didn't come back, and that was it. They offered
me back then a talk show deal, but it went away,
it didn't happen, and I was just.

Speaker 3 (24:29):
Like, oh man, cause I loved it so much.

Speaker 1 (24:31):
So then I went out and tried to pitch my
own talk show, and that's when everybody told me no.

Speaker 3 (24:37):
I mean, I had made like a little sizzle reel yep.

Speaker 1 (24:41):
And I said to one lady at a network I
won't name, Oh my gosh. She was like, I don't
need to see it, and I said, well, it's only
like literally three minutes, but it kind of will show
you what I did when I filled in for Wendy
and kind of.

Speaker 3 (24:54):
What I envisioned it. She goes, I don't need to
see that.

Speaker 1 (24:57):
And at the time, I think Kelly Clarkson had her show,
and it was another woman that had a show and
don't remember her name.

Speaker 3 (25:03):
She's like a motivational speaker.

Speaker 1 (25:05):
And they're like, well, maybe we can put you on
a show with a bunch of chefs.

Speaker 3 (25:09):
And you don't know how to cook, but you learn
to cook with America. That's how you doing these meetings.

Speaker 1 (25:17):
I know, you learn to cook, like it's the brightest
damn idea, right, And I'm looking at this lady going
I don't cook. I like order door dash or like,
I don't know how to cook and I don't like
and she's like, but.

Speaker 3 (25:31):
America would love it. Uh.

Speaker 1 (25:33):
And she basically told me all the reasons why it
wouldn't work with me. Singular talk show host don't typically
do well, and you know they want younger. And I said,
but I am a comic, like I can make magic
where there is none, and the silence is where I
excel at being funny, and I have it on a
sizzle room and she goes, I don't need to see it.

Speaker 3 (25:55):
I think I left that meeting crying.

Speaker 1 (25:57):
Then another person told me, you know your little how
they could tell me I weighed too much your little
you know, maybe slimming down and this.

Speaker 2 (26:07):
Is kind someone said that to you within the past
couple of years.

Speaker 1 (26:13):
Yeah, so it had to be it was right after
I left you. So it was around two thousand fourteen.

Speaker 3 (26:19):
Oh my god.

Speaker 1 (26:21):
So it wasn't like you're too fat. It was cause
you have to do they have to colde it. It
was just like, this is kind of what people are
looking for a talk show and it was no, and
it was I was devastated. And then I went to
a network where they were like this. This is why
I don't I don't believe anybody tell us signed to check.
The lady was like, I don't even need to go

(26:43):
to anyone.

Speaker 3 (26:44):
You are what America wants.

Speaker 1 (26:46):
I have chills running down my arm. I saw you
fill in for Wendy. We you're gonna hear from us.
Six weeks later, I was like, well, what what's going on?
They have picked another host that was on the air now.
She's absolutely amazing, and it was devastating. I couldn't stop
crying because I was like, I've wanted this dream for

(27:07):
so long and everybody's saying no, but it comes back around,
like you don't let your dream die. I put it
on the shelf with the Fine China, and I hosted
a game show. I think I might have hosted a
It was like a littal short lived game show. I
did more acting, I went on the road and did
stand up. All of that made it made me that
much stronger for when they offered it to me again

(27:30):
and again, so with you bring it back to Wendy.
They wanted me to come in and fill in for her,
and my ratings were great because I was the only
one that loved doing pop culture like I guess, and
that was a format that worked for her. So I
came in and sat in for her, and I kept
sitting in for her. I think even there was a

(27:52):
conflict because Ellen wanted me to come on her show
and I hadn't been on her show in twelve years,
and so it was a big conflict. But it worked out,
and I was an audition nation and they were saying, no,
you can't go because you're supposed to be here, but
they let me do it, and so I litterly was
on there and I said, I know they're going to
offer me.

Speaker 3 (28:11):
They're going to offer me.

Speaker 1 (28:12):
So her time was ending, her contract was up, so
they offered me a deal, and her time slot was
still there. You know when networks, they don't ever want
to lose the time slot, right because if you lose
your time slot, you don't get it back.

Speaker 3 (28:25):
They filled it with local programming.

Speaker 1 (28:28):
So her contract was ending and I just stepped into
that time slot. So typically talk shows take a year
or two to develop. I developed mine in thirty days.

Speaker 2 (28:38):
Okay, there's so much I want to get into here.
Because you just said so many great things. I can
relate completely because I'm in this business too, and I
develop as well, and I've shopped one thousand shows, gotten
a thousand no's, yeah, also gotten. We love this, we
can't wait for this, let's do it, let's sign a
development deal, and then another executive comes in and it poof,

(29:00):
it's gone.

Speaker 3 (29:01):
And it's so exhausting and emotional. Yes, and you just.

Speaker 2 (29:07):
Got to get used to a lot of rejection. But
it's hard when you put something, as you said, I
put it on the shelf. When you put it on
the shelf, that is agonizing, absolutely, because you don't know
if it's going to come back around. I mean, you
just said it comes back around, and you hope that
it does, and it did for you. But it's so
hard to get through that and keep going, Just keep.

Speaker 3 (29:30):
Going, Essie.

Speaker 1 (29:31):
Let me tell you how devastated I was because when
I say I had to put it on the shelf.

Speaker 3 (29:35):
Yeah, I didn't want to put.

Speaker 1 (29:36):
It on the shelf, but I said, I said, mentally
and emotionally, heart, my heart can't take another no, because
I knew how I would be different from other hosts,
and I knew all I need is a shot if
you can just see what I can do, and nobody
would give me that shot and that was it. So
I said, I'm just gonna I can't think about it

(29:58):
anymore because it hurts too much. And when I went
the show Dish Nation, which it takes it's a little
pop culture show, they called and they wanted me to
move to Atlanta, and I said, I can't move to Atlanta.

Speaker 3 (30:10):
I'm in LA this is where I got to be.

Speaker 1 (30:12):
But I had a meeting with them, the people who
do it, and in the meeting, this is what I
was our girl.

Speaker 3 (30:17):
In the meeting.

Speaker 1 (30:18):
My managers they know whenever I'm having a meeting, talk
to them about a talk show for me.

Speaker 3 (30:23):
So they say, we had a great meeting.

Speaker 1 (30:26):
They were like, you know, we're going to do it
in LA in Atlanta at the same time. And so
my manager says, well, Sherry's really what she's really interested
in is a talk show. So what can we look
at in the talk show space girl. They said to me, well,
you know we already have.

Speaker 3 (30:43):
We already have Nick Cannon.

Speaker 1 (30:45):
And when I tell you, I burst into tears, not
because I was upset at Nick, but when we filled
in for Wendy the people who had who they had
a comedy panel, but the people who were singular hosts
were Kiki Palmer, Michael Rappaport, Jerry O'Connell, Nick Cannon.

Speaker 3 (31:04):
Me. Everybody had gotten a deal.

Speaker 1 (31:06):
Jerry O'Connell had a six week test deal, Michael Rappaport
had like a test deal. Keky Palmer went to g
M A three with Michael Strahan and Sarah Haynes. Everybody
got a talk show deal except me.

Speaker 3 (31:20):
Yeah, like, no, no, Jerry had nothing.

Speaker 1 (31:24):
And so when they said they said, well we're doing
Nick Cannon, his show is supposed to start this fall,
I burst into tears, like and I had to wipe
my eyes, and I said, oh, I'm sorry I didn't
meet you know, so happy for Nick. And we came
downstairs in the parking lot and I started crying again
and my manager starts crying.

Speaker 3 (31:43):
And I go, what are you crying for? But what
are you crying for? You you get commissioned? Why are you?

Speaker 1 (31:49):
And he's like, but I've been with him so long,
we're attached at the hip, And I said, everybody who
filled in got a chance to do it except me.
Then you start feeling like, well, what is it about
me that everybody is saying no to? I got a
great idea, but it's sometimes it's a timing thing. See,

(32:12):
somebody said, I was in church and they said, sometimes
your dream doesn't happen because you got to mature into
the reality of it. And because that if if something
happens it's a crash and burn, you have to have
enough up under you said that when you can get
back up and have the fortitude to keep going in
the strength. A lot of these people on TikTok and

(32:34):
social media, they get this overnight success, right.

Speaker 3 (32:37):
Unfortunately you're hearing about people.

Speaker 1 (32:39):
Committing suicide, yes, TikTokers, and it's overwhelming.

Speaker 3 (32:43):
They don't know how to handle it. They don't know
what happens when it's too much pressure and or when
it goes away, or when it goes away. We know
you and I, Oh, when stuff goes away, we know
what to do.

Speaker 1 (32:55):
We know exactly how to pivot and go. Okay, what
we cry or whatever? However we do it?

Speaker 3 (32:59):
What's next? Yeah? Where do I need to pivot? Yeah?

Speaker 1 (33:03):
And I think that it was a timing thing that
you know, and I'm very spiritual. God knew I couldn't
handle this dream in my thirties because I'd be out
in the street, I'd be a whole.

Speaker 3 (33:15):
I'd be a hole. Who want to go out with me? Girl?
We gonna be sniffing?

Speaker 1 (33:24):
What? Because I was out in the streets, Girl, I
was insecure.

Speaker 3 (33:30):
I'm just telling the truth. Girl.

Speaker 1 (33:32):
You know, my self esteem wasn't high. So in my
I wanted people to like me. I'd have been at
parties I wasn't supposed to.

Speaker 3 (33:40):
Girl. The FBI would have been like, what party was Sherry?
Not yet?

Speaker 1 (33:45):
Every time we turn on the damn tape, Cherry in
the you know. So it had to happen at fifty four,
where I'm more grounded where I want to go. You know,
I stay at home, but I have a lot of
life underneath me. Yeah, that's when it happened because I've
had the dream for over twenty years and.

Speaker 3 (34:03):
I get that.

Speaker 2 (34:04):
And I feel the same way looking back at my
career because I have the opposite of imposter syndrome.

Speaker 3 (34:09):
I think you probably do too.

Speaker 2 (34:10):
Where I don't feel like I'm a fraud, I feel like,
why aren't you giving me more opportunities? Like I know
what I can do, and I know what I can't do,
But I know what I can do. I want it
always more opportunities, and looking back, I'm glad there were
things I wasn't.

Speaker 3 (34:23):
Ready for ye when I thought I was.

Speaker 2 (34:26):
And I'm glad I'm you know, at a point in
my career where you know, I worked super hard in
my twenties so that when I got to thirty, I
could have a family and I could relax a little
bit because I had done so much. Yeah, and then
I'm ramping it up again as my son gets older.
Like it all worked out, But in the middle of it,
when you're not getting the thing that you know you
can do, that you know will work, it's hard to

(34:48):
tell yourself, Oh, the timing is just not right.

Speaker 3 (34:51):
It'll come. It's just hard. But I think the biggest
thing is what we do.

Speaker 2 (34:55):
You got to know how to pivot, Yeah, exactly, just
kind of keep working and pivot and where can I
be relevant and where can I put my skills to
use and look for these open doors?

Speaker 3 (35:05):
Can I say one more thing about that?

Speaker 1 (35:08):
A girlfriend told me when I was going through the
mass devastation of the nose for the talk show. She said, Sherry,
instead of asking for permission from them to give you
a talk show, why don't you start your own. That's
when I started my podcast Two Funny Mamas with my
best friend Kim Whitley. I said, because this is something
that we can control, Kim, because she was going through

(35:30):
her no season. We can control it. It was only
and then I researched it. I got our LLC everything, and.

Speaker 3 (35:38):
Then the pandemic hit. I was supposed we supposed to
shoot it.

Speaker 1 (35:40):
At Kevin Hart, Kevin Hart's podcast studio. Jamie Fox wanted
to produce it.

Speaker 3 (35:46):
COVID hit.

Speaker 1 (35:46):
Oh my god, we had to stay at home, but
we put it on the air anyway. Yea two NAACP
Image Awards later. Like our fan base is so loyal
when we have a business we sponsor they literally by
thousands of dollars of whatever because they trust us. And
that podcast got me a development deal with a company.

(36:09):
They wanted to do a sitcom with me because they
went on It was one of my rants during COVID
of My Vagina's Lonely, and I went on a whole
ramp by like I was sick of my son, I'm
sick of my dog, I'm scared, I'm in this house,
my Vagina's lonely, and this company, the.

Speaker 3 (36:26):
Studio heard it and they gave me a development deal.

Speaker 1 (36:29):
It didn't happen because I just the conflict of time
with my talk show. But I pivoted and did something else,
and I think that kind of opened it up because
I wasn't thinking about that talk show.

Speaker 3 (36:39):
I think, no, you're right.

Speaker 2 (36:41):
And I had been asked to consult on Aaron Sorkin's
HBO show The Newsroom, and I loved that, but that
was a very serious show about the news. And then
I got asked to consult on Apple TV's The Morning Show,
and I see all these comedians are going to be

(37:01):
in it, you know, Reese and Steve Carell and Jennifer Aniston.
And I'm like, oh, good, this is going to be
a comedy about my business.

Speaker 3 (37:07):
Great.

Speaker 2 (37:08):
I go to consult writer's room all that stuff. It
turns into a drama. They turn it into a drama.

Speaker 3 (37:14):
So then I'm thinking, gosh, I can't.

Speaker 2 (37:16):
Wait till someone writes a comedy about my business and
then asks me to consult on it. And I'm lying
in bed one night and I said, well, why don't
I just write it?

Speaker 3 (37:25):
Why am I.

Speaker 2 (37:26):
Waiting for someone to ask me to consult on something
they've done?

Speaker 3 (37:30):
I can write it. So I did.

Speaker 2 (37:31):
I wrote the pilot. This is the show that, like
your talk show, I just really really believe in and
I still do and got all the nose, but I
wrote it. I got really positive feedback, and doing it myself,
whatever happened to it just felt really good because now
I'm in charge, I'm in control, and we're in a business,

(37:53):
you and I where everyone else is in control of
our fate. It feels like at all times that's hard.

Speaker 3 (38:02):
That is a tough space to live in.

Speaker 2 (38:03):
And when you finally get the agency, like you did
to say, I don't want to.

Speaker 3 (38:08):
Fill in on the comedy panel. Yeah, I want to
do two days.

Speaker 2 (38:11):
I want them to be these days and I wanted
to When you finally get that agency, it's just such
it's so empowering.

Speaker 3 (38:18):
Yeah, it was. I'm thankful. I have a you know,
people of my team who believe in me. My team.

Speaker 1 (38:26):
I've been together with them ten years, you know, and
normally you're with agents who if you're not bringing in anything,
they drop. You might have always believed in me, and
everywhere they went. Talk show hosts was on there, yes,
you know, pushing I got a publish everywhere I go,
she's going, can we push for chery to get a
star on the Hollywood Walk of Fame.

Speaker 3 (38:46):
This is what she's like.

Speaker 1 (38:47):
She's never stopped. So I got those kind of people,
and I'm very very glad, right.

Speaker 3 (38:52):
Can I read your script? Yes? What would you mind?

Speaker 1 (38:56):
Because because I love that and I love sitcoms, I said,
I really would love to do a comedy, a single
camera Yes, comedy different from the sitcom of a talk show,
because the dattlings behind the scenes that nobody knows about,
the the things that Barbara Walters used to go through

(39:20):
with Diane Sawyer because there was always everybody knew that,
there was always that that thing right here because they
were both trying to get the same guests, the stuff
that I go through being a talk show host, and
my other compatriots colleagues.

Speaker 2 (39:35):
Yeah, girl, if only people knew I feel the same way.

Speaker 1 (39:38):
I just when I get done with this, I want
to do something like that. Because I used to watch
Larry the Larry Sanders Larry.

Speaker 3 (39:45):
Sanders Did you and I?

Speaker 1 (39:49):
He could only he could only have sex when he
watched himself on the show. That was my favorite episode.
I just would I would love to read it. Well,
that's connection, That's that's networking.

Speaker 3 (40:03):
Well, I love that absolutely. You can read this absolutely.

Speaker 2 (40:20):
You and I have talked about our sons and mental
health a bunch.

Speaker 3 (40:24):
Yeah, it's important to both of us.

Speaker 2 (40:27):
And I know Jeffrey is the love of your life
so much like my son is the love of my life.
And talking about him for me too is important. Like
you know, he is a huge part of me, and
I love talking about him. What parts of you as
a mom wanted to explode publicly with your love and

(40:50):
what parts of you as a mom really wanted to
protect him and keep him, you know private.

Speaker 3 (40:55):
You know. So for me, I've always talked about you, Jeffrey.

Speaker 1 (41:00):
I've always talked about from the how he was conceived
with fertility and he's just always been a part of
my life. So people recognize Jeffrey from me bringing him
on the view and just literally he's nineteen. About a
year and a half ago, Ssie, he said to me
because we were at a dunkin Donuts and he went

(41:22):
the wrong way and I was like, ooh, this is
gonna be good for the sitting in the chair when
I talk about Jeffrey, And he looked at me and
he said, don't talk about me. I'm not a story.
And I guess a teacher at a school laughed and said,
your mom can make a story out of anything. And
because my son is on the spectrum, he's got it.
They used to say Asperger's, but they say on the spectrum.

(41:43):
So he takes everything literal. Yes, my son, he does
it like nuances and things like that sarcasm.

Speaker 3 (41:51):
So he said, I'm not.

Speaker 1 (41:52):
A story, don't talk about me, don't show my picture.
He's adamant. And I broke down and cried and I said, Jeffrey,
that's my label, Like I'm a mom. Like if I don't,
I'm not dating anybody. I don't go anywhere. You're all
I got, Like you're my money. Yeah, like that's you're
all my jokes.

Speaker 3 (42:12):
And and now.

Speaker 1 (42:15):
At nineteen, he's going through stuff that I want to
talk about. That is so funny that I know mothers
of teenage boys go through and the angst that they
go through and how me is and he doesn't.

Speaker 3 (42:28):
Allow me to talk about it.

Speaker 1 (42:30):
It is literally, but I have to respect his privacy
because Jeffrey did not ask for this.

Speaker 3 (42:35):
That's right. I did, that's right.

Speaker 1 (42:38):
And I don't want him ever looking at something and
him being humiliated because I talk to other comics and
they're like, nope, that's how I pay the bills, you know,
until you move out.

Speaker 3 (42:48):
But I go, no, I have.

Speaker 1 (42:50):
To respect Jeffrey even though everything he does every single
day I want to laugh at and I know other
people would and I beg him. I go, if I
paid you for the joke, Jeffrey has no concept of money,
so that doesn't work. Paying her for the joke, me going, Jeffrey,
look at how many likes we get.

Speaker 3 (43:06):
What we do?

Speaker 1 (43:07):
You know, little skits together on Instagram means nothing to him.
I've chosen to keep his life private. I'm trying to
see if I can give Kelly Ripper used to call
her son the one that shall not have a name,
or something like, Yeah, if I can go my friend's son.

Speaker 3 (43:26):
A wink wink, we'll call him Schmefrey. We'll call him Schmefrey. Yeah.
But I gotta respect that.

Speaker 1 (43:33):
So I do keep his life private because now people
are recognizing him.

Speaker 3 (43:37):
He's a nineteen year old. He's an adult.

Speaker 1 (43:40):
He's an adult, and he deserves that. So now I
got to get a life. Like I said, I got
to get pregnant. I need somebody to give me pregnant.

Speaker 3 (43:46):
I need more material.

Speaker 1 (43:47):
I need more material, girl, because I can't keep talking
about a p dietris cutting my bunions open.

Speaker 3 (43:53):
And oh my gosh.

Speaker 1 (43:57):
Oh no, So I'm now talking about my dates that
I go on and you know, talk, but I refuse
to name anybody.

Speaker 2 (44:04):
Oh oh, why are you seeing people that people would know?

Speaker 3 (44:08):
It was a couple. It was a couple of times.

Speaker 2 (44:10):
Yeah, that whole You can't tell You can't tell me
any of them now that it's over, No.

Speaker 3 (44:15):
Because you'll know, you'll know who it is.

Speaker 1 (44:17):
And it's always it's good, yes, and it is some
good stories.

Speaker 3 (44:20):
But I'm like, I don't want you know, man, I
would love to, but but they didn't work out. Now
it didn't work out. It's hard dating. Yeah, one was
a comic. It's hard dating comics. I married one. It
was worse.

Speaker 1 (44:34):
It's really hard. It's actors. It's really hard. I'll tell
you some of the stuff that that's telling. One actor,
he's an actor, he's been in big movies. He came
to a comedy show that I did. It was great,
and he I gave him my number. Really cute, muscular.
And he calls me and he's like, I've had crush
on you for a long time. And I'm like for
real and and he said he wanted to take me out.

(44:57):
I was like, okay, absolutely god, and he said, but
I have to be honest with you. He said, I
have a girlfriend. As a matter of fact, I have
three girlfriends. He's into that poly poly ammor thing. And
I'm sitting there on the front. I'm going, so you
have three and he goes, yes, I have my main
one and on the weekends, I don't it's her weekend.

(45:18):
Then I have the other two and they don't know
about you. They're very, very open. And I was like,
so you want to you want to bring me in
what other women?

Speaker 3 (45:26):
And I said I can't. No.

Speaker 1 (45:28):
I'm very glad you're honest with me, but I can't
get down with that. And he's like, he's like, I
literally I'm not looking to get married, but I know
if you're at home and you just need somebody to
come over, and he said all the stuff that he
wanted to do to me.

Speaker 3 (45:41):
Oh my god.

Speaker 1 (45:43):
He said, I'm that person and you could call it,
you know, And I was just like, I hate. As
wonderful as that sounds, I can't.

Speaker 3 (45:52):
I can't do that. No, that would not be appealing
to me at all.

Speaker 1 (45:57):
So every time I see him in the movie every
day and he's got his manger, they are always he
posts her but not the other two and.

Speaker 3 (46:04):
She's like, she's really smart and she's down with it. Oh,
he loves me. Do people know that he's got other
side pieces? No, like the public, they don't know. It's amazing.
I'm telling the stuff that goes on behind the scenes.
You know.

Speaker 1 (46:21):
It's one that flew me in, flew me on this
private plane where he was going to be.

Speaker 3 (46:27):
I can't.

Speaker 1 (46:27):
I just told you, I can't say the name. Flew
me in on a private plane. He rented out a big,
huge mansion because he was on comic on tour, so
rented out a beautiful, beautiful place. It was an amazing
weekend and amazing, but it was like, you know, but
once just the two of us together was amazing. But

(46:49):
going out now in public, everybody knows who this person is.
It's yeah, you know, I'm kind of walking nine steps behind.
And it was it just was too much. We could
even we couldn't make that work.

Speaker 3 (47:01):
So would you want to be with someone who's not
a celebrity.

Speaker 1 (47:06):
I would like to, but I think it's hard. For
what's been hard dating a regular person is my life
is so busy. It's hard for me to give you
the attention that you need. It's hard for me. I'm
always on the road, I'm always I traveled twice a month.
I'm always it's Jeffrey, it's the talk show, it's branding deals,

(47:27):
it's stand up, it's writing a book. So it's a
person who's as busy as me understands that life, right
Like the person who flew me in, he was so busy.
I didn't talk to him again for months because he
was so busy. The actor, the actor that I was
talking about, he's in another country making a movie right now.

Speaker 3 (47:47):
So it's like those people understand your life.

Speaker 1 (47:51):
Yeah, And I guess if I didn't work as much,
I've been with people who were I don't want to
say regular, but they just do regular, typical jobs. And
it was always like, Sherry, can I walk the red
carpet with you?

Speaker 3 (48:04):
Can? Can I? You know?

Speaker 1 (48:06):
I have a script I wanted to write. Could you
show it to somebody? Or why aren't you spending time.
Can you just spend some time with me? So that's
the hard thing.

Speaker 2 (48:15):
Yeah, it's easier with people in the business to understand
your business.

Speaker 1 (48:18):
Yeah, there was a guy who was he was a
vice president of a corporation and he's really busy. But
he's like, I fly into New York, and when I
fly into New York, can we go out to dinner?
So when he flies out, will go out to dinner.
There was a chef. There was a big, a huge chef.
It was just like now that one was a who
you know? But he was very, very busy at the time.

(48:43):
Chefs are great.

Speaker 3 (48:43):
They could is he a TV chef or like a
chef chef? I'm gonna stop writing. You absolutely know him.

Speaker 1 (48:51):
You know him and and you know so he would
call me when I was on the road and we'd
be flirting back and forth and it.

Speaker 3 (48:57):
Was almost we were going to meet up. Girl.

Speaker 1 (48:59):
That was like that was too hot to try. I
was at a restaurant one time. He brought me something
he made for me, some dessert. You know, Oh, I
had some good I'm I should I have to write
a book.

Speaker 3 (49:13):
Yeah.

Speaker 1 (49:14):
At one point about who these maybe not give their
names with more detail.

Speaker 3 (49:19):
Yeah. Yeah, so I get to I do get to
have fun.

Speaker 1 (49:22):
And I've learned and now at this season, to keep
my stuff private because I think sometimes so many people
overshare and then when something goes south, you go, oh,
please respect my privacy and them, you know, on social media,
it's like.

Speaker 3 (49:35):
Nope, you let us in, you open up the door.
We want it all.

Speaker 1 (49:40):
That's right, And I don't want I don't want to
be making no documentaries and how I fell in love
and I was like, j Lo.

Speaker 3 (49:47):
You better stop that girl. This is not going to
work out. Oh boy, did that not work out? I
was like, you keep your stuff to yourself.

Speaker 1 (49:54):
Stop making documentaries and all of this and asking for it.

Speaker 3 (49:59):
Yeah, because too many people in your business. Yeah, well
she invited them into her business.

Speaker 1 (50:03):
You invite people in and then you can't you can't
put them out.

Speaker 3 (50:07):
So why now I go, I'm not inviting you in. Yeah, Okay,
we're gonna do a bit of a lightning round.

Speaker 2 (50:13):
Okay, you've already interviewed presidents and first ladies and a
list actors.

Speaker 3 (50:22):
Who's someone you want to interview but haven't yet? Meryl Street?
Oh good one. I love Meryl Street. So much.

Speaker 1 (50:29):
I want to talk to her about her career. Michelle
Obama and that guy that she's married to can come along.

Speaker 3 (50:37):
I would love to ask him some questions. Yeap. Who
else I love?

Speaker 1 (50:41):
I just love intelligent people who have a sense of humor.
Trevor Noah, It's what I want. It's been so hard
trying to get that man on my show. Huh. And
and I think Jeremy Renner, I really want to come on.

Speaker 3 (50:54):
Oh yeah, I've got a story.

Speaker 1 (50:56):
He's got a story, and I love his story. And boy,
I think right now they said it's in the entertainment
fields a great list.

Speaker 2 (51:06):
Who is the funniest comedian ever? And who's the funniest comedian?

Speaker 3 (51:09):
Right now? Who is the funniest comedian ever?

Speaker 1 (51:12):
He gets I will one of the funniest comedians ever.

Speaker 3 (51:19):
I don't know who I could say is one of
the funniest.

Speaker 1 (51:22):
I know who I've always loved is Whoopy Goldberg. I
used to watch her when I was younger, and you know,
to work with her was it was.

Speaker 3 (51:30):
Like a dream.

Speaker 1 (51:31):
She's so talented, so talented, And who's one of the
funniest now?

Speaker 3 (51:36):
Yeah, I love Oh my.

Speaker 1 (51:37):
Gosh, oh you put me on a spot girl because
I'm trying to remember some of these comics that I
know who are so funny that I came up with.
Chris Rock will always be a favorite of mine.

Speaker 3 (51:49):
Yea, Chris Rock.

Speaker 1 (51:51):
And I'm mad at Chris Rock because he's supposed to
verify me for rayah and he has not verified me yet.

Speaker 3 (51:57):
I get on that.

Speaker 1 (51:58):
I'm like in a pending status because you need a
select you know. You can try to get on Ryo,
which is the dating site for like if you're in
the business, but they'll put you in and they'll put
you into like oh you gotta wait. But if you
get a celebrity to verify you, then you're in.

Speaker 3 (52:13):
And Chris does not need anyone to verify you.

Speaker 1 (52:16):
No, yeah, they said I need somebody to verify Well
maybe not now, but I've been on Hole for three
years and that's Chris Rock. Yeah, that's Chris Rock's fault.
So Chris Rock will always wander sights. I love there
and oh my gosh, it's so many. Yeah, my memory
is going because I'm like their comics that I love.

Speaker 3 (52:37):
Yeah, that those those are good ones. Who's your favorite
view co host?

Speaker 1 (52:44):
Oh my gosh, my favorite view I was like Meredith Via,
She's just great. She's just easy going and cool, no controversy.

Speaker 3 (52:54):
No druma. I love you know. I saw the other
day Nicole Wallace, Uh huh. She didn't know what was me.

Speaker 1 (53:00):
She kind of went past me, and I was I
didn't want to be all ghetto because we were on
the Upper East Side and go no.

Speaker 3 (53:08):
She looked like she had come from jogging. So I
love I.

Speaker 1 (53:11):
Love Nicole Wallace, love Joy Behar her mouth. You know,
we got no more fights, but I spend more time
with Joy Behart, Lizzie Hasselback and our bestess of friends
on the show because we pray together all the time.
And but I love them all. Whoope has her point
of view that she brings. I just I got along

(53:33):
with all my co hosts. Jenny McCarthy was so great.
She didn't have a good time on the show, but
she had a good time with me.

Speaker 3 (53:40):
Good good Genie.

Speaker 1 (53:42):
Don't even like talking about the view. There was a
time literally Jenny and I love Jenny because I did
a sitcom with Jenny a pilot way back when I
was thirty four years old, and I think Jenny was
around and we played.

Speaker 3 (53:55):
Horrorse that's literally what we played.

Speaker 1 (53:57):
Like. We played two women who slew with everybody, and
it was very it was very funny, and it didn't
make it onto Fox. But Jenny would not do her
homework and they got on my nerves. Like I went
and saw everybody at the theater all the you know,
I read the books, and so I saw everybody's movie
because they would have private screenings. And we go back

(54:18):
in and Barbara would say, dear, did you go and
see the movie? And Genny would go, yeah, Donnie.

Speaker 3 (54:23):
And I we went and it was so ethereal and.

Speaker 1 (54:26):
The way they would act, and I was like, bitch,
you didn't even go. You wasn't even there.

Speaker 3 (54:30):
You and Donnie. I was there and I.

Speaker 1 (54:33):
Didn't see y'all nan nowhere in no seats. And she
and Barbara would say good dear, and I was like, ooh,
I want to call you out so bad because you
didn't read that book, you didn't go to the theater.
And so I love having We had a lot of fun,
but Jenny one day, I guess it just wasn't working.

(54:55):
One day she was wearing glasses all the time and
like these button up shirts.

Speaker 3 (55:00):
So I said why are you dressing like that?

Speaker 1 (55:02):
They hadn't made that girl wear glasses so she could
appear to be And I said, they knew you was
in Playboy, whatever you did, they knew you and who
you were. And that's the behind the scenes of talk
show because she I was like, what is this with
this look with the glass? Now you look like a
sexy school teacher that's trying to flirt with your students.

Speaker 3 (55:24):
Is that what they want you to look like? Uh?

Speaker 1 (55:30):
I was Jenny's lifeline on the show. When they told
us both we weren't coming back, we all got drunk.

Speaker 3 (55:36):
It was great. Yeah.

Speaker 2 (55:40):
Okay, you mentioned in Suddenly Susan. You played two different
characters on Suddenly Susan.

Speaker 3 (55:46):
Who are they?

Speaker 1 (55:47):
I don't know the first character I played because that's
when I came in as a guest star. Okay, so
I don't remember. But they called me back because Brooke
loved me so much. They called me back to be
a series regular, and I played the secretary of Eric.
Was it Miranda or something? It was Miranda. It was

(56:09):
Miranda Charles. I love that role so much. I played
Eric Idol his secretary, and that was one of the
bright spots of my life. I met Andy Dick, who
am really good friends with even to this day. Well,
we went through it that needs to be in the show. Well,
oh my gosh, me and Andy went through. But I

(56:29):
met Andy Dick and then we did a sitcom Less
than Perfect, and that's when Andy Dick and I became
really really good friends.

Speaker 2 (56:36):
So a person you played on Suddenly Susan was named
Ronnie Ronnie that's right, Oh my gosh. Well, in addition
to playing Ronda on Friends, where else do you play Ronda?

Speaker 1 (56:52):
Oh?

Speaker 3 (56:52):
The Emerald Lagassi Show. No, No, I didn't play Ronda
on that. Ronda, Ronda? Ronda? Else did I play Randa?
I'll give you a hint. It's a movie. It's a movie.
It wasn't Beauty Shop, was it? No? Oh my gosh,
it wasn't. It wasn't the movie with Kiki Palmer Carlina White. No,

(57:15):
it was Ronda. It wasn't with Alvis Hodge.

Speaker 2 (57:20):
Where else did I play Ronda girl Transformers?

Speaker 1 (57:24):
Well, for first of all, my scenes got cut out
of transform Really Michael Bay. I auditioned for Michael Bay
and he told me to improv, and I improved all
of my scenes and they put me in Transformer two
scenes and it was Josh Dumal. Dumaal wasn't in the movie, huh.
He came to it, showed my pawn shop. He came

(57:47):
into my pawn shop and I and I told him
I wasn't gonna give him no guns unless he took
his clothes off.

Speaker 3 (57:53):
And it was great, and they cut it out. And
I tell you why.

Speaker 1 (57:55):
I think they cut out because Michael Bay wanted me
to do some free stuff for some some deal he
had and my agents was like, my agents like sharing,
not coming to help sell your telephones. And all of
a sudden he loved me, Michael Bay, and all of
a sudden, my scenes were cut out. But I'm still
I think I was in the credits. Yeah, I still

(58:16):
get like a little check. But my scenes were cut out.
I think because I told Michael Bay, now, but I'll
sell your telephones. Now put me in another dog on
No I will now.

Speaker 2 (58:27):
Okay, we share something in common. We both did Celebrity Jeopardy.
Who were your competitors and how did it go?

Speaker 1 (58:36):
My one competitor was the guy that's on Lauren Order SVU.

Speaker 3 (58:40):
He's he's a serious.

Speaker 1 (58:41):
One with Mariska Hargate okay, and Chris Maloney. Chris Maloney,
Chris Maloney, I'm not good with names. And there was
an other young lady. She's like on ESPN and she's
really funny, like she does com really great. It was
those two secret to that. And you know it's hitting
that buzzer. You got it. It's all about the buzzer.

(59:02):
You got to get approved with that buzzer. But also
they both left with because we were all playing for
a charity, and so my charity.

Speaker 3 (59:12):
I would never see, like you good at a Jeopardy.

Speaker 1 (59:15):
I could never Jeopardy is not the lane I swim
in one hundred thousand dollars pyramid, that's the Hollywood Game Night,
all of those, but Jeopardy.

Speaker 3 (59:24):
I look at it with my grandmother. I huh. So
they've always asked me.

Speaker 1 (59:28):
I've always said no, but because of the charity, I said, yes,
no one share you walking into death.

Speaker 3 (59:35):
You know you ain't.

Speaker 1 (59:37):
And I said, but I'm doing it for this charity
because they get I think they gave our charities. Even
if you lost, you got the charity got thirty thousand dollars. Yeah,
you can win a million something. Lisa and Walter from
mamb of Elementary.

Speaker 3 (59:47):
That's her.

Speaker 1 (59:48):
That's her jam. She know a lot about nothing. That's
my girlfriend. She know a lot of opinion about a
bunch of nothing. So when I went in there, when
I tell I thought they was gonna give us easy
questions for the celebrities.

Speaker 3 (01:00:03):
When I tell you them to have questions, they were
like in.

Speaker 1 (01:00:05):
Roman eighteen nineteen forty five, post Jesus, what was And
I was like.

Speaker 3 (01:00:11):
I don't know.

Speaker 1 (01:00:12):
I don't know what that answer is. And then if
I did know it, I couldn't get the buzzer. So
they would say it and I was like, they I
couldn't get the buzzer. And I was like, that's what
I was gonna say. And the girl from ESPN said, share,
you gotta trust your gut and I go, well.

Speaker 3 (01:00:26):
Hey, bitch, you winning. Now you're telling me to trust
my gut.

Speaker 1 (01:00:29):
Right, So everybody, I'm telling you sc Chris Maloney had
like sixty four thousand dollars. The girl from ESPN had
seventy two thousand dollars. Ask me how much I had
about seven hundred dollars, but you couldn't tell. I had
the most fun on Celebrity Jeopardy did. They loved me,

(01:00:52):
and I was so happy. Rosie O'Donnell even made a
post saying why I should have never did it and
I should fire my team because I look so But
I said, you know what, it wasn't about me.

Speaker 3 (01:01:03):
That's not why I went on there.

Speaker 1 (01:01:04):
Yeah, I was willing to make myself look crazy because
my charity got thirty thousand and every time they run
that show, people donate to her chair her organization.

Speaker 3 (01:01:15):
Like people have put her in the will.

Speaker 1 (01:01:16):
They're like, when I die, I want five thousand a
month to come to you. She's made so much money
from me looking silly.

Speaker 3 (01:01:23):
I didn't take myself seriously. Yeah. Yeah, it's a tough
show to do though, it's how did you do well? Sherry?
I won, but I see, I know it. That's why
I said that. That's something you came.

Speaker 2 (01:01:36):
Down to the wager at the end, and you know,
it really could have gone either way.

Speaker 3 (01:01:41):
And I was on with some very smart people, but you.

Speaker 2 (01:01:43):
Know it was I was very nervous because you can
get very embarrassed coming into that, coming into that show,
but it went okay.

Speaker 1 (01:01:50):
No to self when they call me back for Celebrity Jeopardy,
because they will they're going because I was so, I
was the entertainment of the show, and I'm gonna tell
them in my contract. Sea Cup is not to be
on the same platform with me. Sea Cup can come
on Wheel of Fortune because I'm a I'm a dominate
you definitely be me. That's my dag on show Wheel

(01:02:10):
of Fortune. I get I get to that, I get
to that left at Sea Cup can come on Hollywood
Gag Night. At Sea Cup can try to beat me
one hundred thousand dollars Pyramid. I will run you into
the ground. I get my people to the Winter Circle.
Okay that, Jeffardy, You're not gonna be on that with me.

Speaker 3 (01:02:26):
Girl, don't worry. Okay.

Speaker 2 (01:02:29):
The final question is the most important to me culturally.

Speaker 3 (01:02:34):
Okay, when is iced coffee season?

Speaker 1 (01:02:38):
I don't know because I drink jasmin tea. Okay, I
don't drink I don't drink coffee. I do mushroom coffee
and I do green I do jazzmine tea.

Speaker 3 (01:02:48):
If you were to drink iced coffee, when would the
season be? It would have to be like around now.

Speaker 1 (01:02:55):
Well, no, it have to be when it's hot, right
like around the spring.

Speaker 3 (01:02:59):
No, in the spring summer.

Speaker 1 (01:03:00):
I would think ice coffee in the spring or the
summer would be great. Why on earth would you drink
an ice coffee now? Unless you like me? You hot flash,
so that would absolutely I'm gonna change my answer to
be dead of winter because that's when I'm hot flashing
the most.

Speaker 3 (01:03:17):
The correct answer is you're round, the correct you're round,
You're round.

Speaker 2 (01:03:20):
Okay, it's always ice coffee season. But as a non
iced coffee drinker, you're at a disadvantage.

Speaker 3 (01:03:27):
So I won't hold that against you.

Speaker 1 (01:03:28):
So you pulling celebrity Jeopardy on me right now. That's
why you're not gonna play with me. Why you're not
gonna play with me?

Speaker 3 (01:03:34):
That was unfair. How you be shady without being shady?
There you go. Well, Sherry, I love you and I'm
so glad you did this. Thank you so much. Gosh,
it was so much fun.

Speaker 2 (01:03:45):
Thank you so fun. And I just love watching you
and all of your success.

Speaker 3 (01:03:50):
You deserve it.

Speaker 1 (01:03:50):
Well, you have to come play with me, please, and
I want to see your script. You have to come
play with me on the couch, okay, perfect, And I
need to read your script like me terrific?

Speaker 3 (01:03:58):
All right, all right, thank you, oh girl.

Speaker 2 (01:04:02):
Coming up on Off the Cup next week, I sit
down with Stephen Weber, star of the nineties sitcom Wings.

Speaker 3 (01:04:11):
How does the role of Brian Hackett come to you?
Good segue? Well, I mean that was first of all,
I was that guy in many respects. I was kind
of a snarky, affable dickhead.

Speaker 2 (01:04:31):
Off the Cup is a production of iHeart Podcasts as
part of the Recent Choice network.

Speaker 3 (01:04:35):
I'm your Host SI Cup.

Speaker 2 (01:04:37):
Editing and sound designed by Derek Clements. Our executive producers
are Mesie Cup, Lauren Hanson, and Lindsay Hoffman. If you
like Off the Cup, please rate and review wherever you
get your podcasts, follow, or subscribe for new episodes every Wednesday.