Emmy Winning Talk Show Host Sherri Shepherd Chats Season 2 of Sherri and the Importance of Comedy

So what's there to say about our friend Sherry Shepherd. We love her. She's an Emmy Award winning comedian. She's had an incredible TV career spanning two decades, and now she's hosting her own talk show, Sherry. Let's talk about how she got her start or incredible work ethic, and what it's like now hosting her own show. Sherry Shepherd, thank you for being here. This is amazing. Having you on our radio show is just a treat and a gift. Let's go a little deeper.

Okay, We're going to turn this phone off, because no matter how much you do to turn off a phone, it still goes off. Like I'm always scared that it just will go off. So basically I just turned it off.

You know what, though, if it goes off, I'd be kind of interested to see who's called his Sherry Shepherd.

Well, the one thing I can always say, it's my son, Okay, even though it's my girlfriend going what you're doing.

Right, that's best son, I got it right. Where are you from?

Originally Chicago?

Yeah, Chicago by way of Hoffman Estates, Illinois, the Northwest suburb.

So and now you're living in New York full time. Do you like being in a New Yorker.

When I tell you I love New York so much, Like everybody goes go to Jersey because you can get more for your money, and I'm like, I'm staying right in New York. I don't care what I gotta do. If I gotta sell avon on the side.

You know, It's like.

People think, don't be thinking I got that Llen one hundred million dollar talk show deal. No, sir, So like you got, you got to be on a budget. So I don't care what I gotta do. I'm staying in New York, in Manhattan, which is expensive as heck, but I'm gonna do it.

But sure is the city is a pain in the ass, and that's what you like about it.

I love it. I love the energy. Like if you go to la and you're most of us are actors. We're in the valley.

It's just like chill and laid back and you get in your car, you go meet up at the park to go walking. Everything is you have to get in your car. You don't take like the bus or the train. That's if you don't have a car and you gotta get there. But it's just very chill in LA when we say, you know, let's get together for lunch, just we just saying goodbye. It's like, so you go to New York and everybody is very real, very authentic.

Too real sometimes or you're okay with that, I'm okay with you know where you're staying with that.

I know where I stand, I know where I'm getting and I live in Harlem, and so there's always something going on.

Even in Manhattan.

There's always it's so many nationalities, and we got a parade for every nationality that is in New York. I'm like, well, who is this now? It's the Turkey. Everybody from over from Turkey. We having a parade like it's it's the Puerto Rican Day Parade. It's the Haitian Day Parade. It's the LGBTQ Parade. It's the people with one leg, they got a parade. It's the people that have no we It's a parade for everything. It's a bike marathon. It's

It's something going on.

I'm making notes here. Slow down the one Legged Parade. I want to be a part of that.

I'm telling you. If it's not there, it's about to come.

And by the way, if if you don't live in New York City, or even if you do, weekends in Harlem is really the best time. And weekends there's always something going on year round, even when the weather sucks. Ass. Harlem is like.

Literally if you go to Melba's restaurant, they block off the streets in Harlem. But Melboa's is especially great because they play double Dutch, they dance.

I mean, it's just a party.

And I go every I walk from my place, which is about thirty blocks, and I walk and we just have a good time, have some catfish strips and we're just in a drink and we're partying. A Babyface was just doing his concert on the Brownstone Stoop.

Just for the It was an announced. He just showed up. Obviously you heard about.

It announce, but everybody came with their lawn chairs. And then Mary J.

Blige was there the next week. So what do you get to go see Babyface? Perform on somebody stoop, not a person who stupid was probably wasn't happy it's on my lawn now on my stoop down the stairs, but it was so I love that energy.

So I walked out of my apartment yesterday, had to run around the corner and get some dog food whatever. And there was a man on the stoop on Broadway meowing at people. And I think I saw him hiss a couple of times. Yes, I'm like, you know, what, what the fuck is going on in the city?

You know, I mean?

But I also had a woman lunge at me which looked like a sharp object in her hand at one time.

You have to be careful, which is like, what are you doing?

And last night in Bedsty, or two nights ago in Bedstide, there was a murder, just for a random I look for a.

Place in Bedstick. Well, so now I'm not you said it was a murder, all right? They gotta go to Cobble Hill.

They murder everyone everywhere. It's it's not just Bedsty.

Yeah, but ain't nobody said, you know, over here in real Good Heights they had a murder. Ain't nobody say to Amy Schumer never said to me it was a murder on her block.

Okay, you're right, But my point is this, we choose to be here. We pay the premium to be here. Yet being here is it's more costly than just cash.

Yeah it is.

It wears you down.

It wears you down.

But I have to say I got to, you know, preface it with I'm very blessed the way I came to New York to live. If I had to come to New York to struggle at this age, I couldn't do it because the New York is really a place where you learn independence, you learn to hustle. This is a place where you got to grind New York. And so I'm very, very blessed that to the both times that I lived here, I was co hosting the view. I lived in the Trump, but well it used to

Well, she'll be calling you, She'll be calling SHERF.

That answer is no, absolutely.

Well, I tell you, And I've told this story before. A friend of ours who works at the show, Josh, he lived in Cleveland and he was dying to move to New York City. He said, Elvis, how much do I need to make to be comfortable in New York City? I said, Josh, billionaires are uncomfortable, and it's uncolling. Said, that's the thing. We love being uncomfortable in this town. It's this self cutting thing. I don't know. I don't get it, but here we are, you.

Know, I don't know. I guess to being uncomfortable makes me try harder. The only thing I hate is I don't have the energy that I used to have when I was uncomfortable, that energy to go out and hit the pavement hard. Right now, I'm too tired. After I make one damn TikTok, I'm like, I got to go to sleep. So this is a I'm blessed that, you know, at this age, just like I'm seeing the benefits of my working so hard and so much struggling that I don't have to.

I don't have to do that hustle.

You can enjoy New York.

I ride the train because I just like riding the train.

Way the train. He always gives you a story, always on the train.

But I do it because I'm trying to teach my son how to take the train and ride the train.

So we keep getting lost, so I'm not teaching them nothing.

But it's not I'm not riding the train because I have to because I have a talk show, so you know, they provide a driver. But I like being on the train because I liked it keeps me fresh as far as like my mind, my creativity. So I'm very thankful that I'm here in this place doing what I do.

You can catch me on the F train today. I'll be the F train. Hey, yeah, the F train.

I do the dow See. I take the If I don't have my reading glasses on, that's when I get lost.

I was going to do.

I'm usually taking like the D train, and it was one time the Broadway show I couldn't get an uber, so I said, let me take the train. Normally, when I ride the train, I don't look like Sheery Shepherd, all right, So yo, cousin Artha, that's what I look like, all right. But I got on the train this time straight off a Broadway show.

So I had this.

Fusia pink puffer coat on, hair hanging down on my butt, lashes that look like stairsteps on my eyes. And I got on the train and it was at night, and I thought the d I thought it was the b Trade and I was like, okay, I'm getting off.

I don't know where I am.

And that's when I look like a tourist because I got off and I kept walking back and forth, going where am I at?

It's a scary moment.

Yeah, And these two people came by and the girls like, I really love your coat. And I was like, oh, I'm in trouble when somebody's like I really love your coat. I'm from Chicago. I know what that means. I'm about to take that coat boy. And I'm walking and I

I was even do you even know where you were?

I was lost?

But where where?

I just got off because I kept going I'm.

Not pass So you got back on? I mean, did you?

But I didn't know how.

When I went downstairs, I was like, I don't see like going to the downtown.

So I don't know if I'm in the Bronx. I'm not. I'm not quite sure where.

The numbers are just high numbers, and I'm like, I don't know, and then the person I want to ask don't look like I should be asking. I got a pink puffer coat on from Chloe Kardashian's line, and some girl just told me she likes it. I'm not gonna have this coat too long. So I was just like, oh my gosh, Sherry, what is going?

So what did you do? You got back on the train.

Some said, bitch, if you don't call an uber and I went, oh, that's right, and Uber, and I'm calling Uber black because I can't talk.

I'm so traumatized.

And they'll find you. They'll find you. You don't even have to know where you are.

Don't find somebody uber black.

When you call it uber black, it's stem Dog on the regular Uber and the regular Lift. They want to talk to you. They got a mixtape. They want you to produce the record for him. You know it smells like the kids and just been in the in the car they you know, they didn't made they lunch and ate it Like I was like, I need a Uber black because I'm so traumatized. I just wanted you get in then Uber black. They don't say nothing to you.

So whoever thought we'd actually be pampering ourselves by getting Uber black? You don't really want to take care of myself to time, I'm gonna treat myself to an Uber black. If you're lost in freaking New York, you should do that.

Were in your pink Yeah, when your nerves is bad, right, you just go that extra and get the Uber Black.

Well, Sherry, here you are. You live in New York. You're in season two of the show now season one? Uh did you know in your heart of hearts this is going well? I bet you there's gonna be a season two or there was there ever? Any how does that work when you have seasons? Do you ever like want did you wonder for a second.

Yeah, I'm always in that state of because that way when it happens, I'm just like so like so pleasantly surprised. I love people who go I already know that that this show is going to be picked up. I already know that we're gonna like I envy that. I wish I could be like that from me, I'm like, please, lord, let it be picked up because I'm having so much fun and I actually I love doing this. I hope they pick it up. So when we got a two season pickup, which rarely.

Happens, oh wait, I didn't know that you got two seasons now for two weeks, so you're guaranteed a three season show?

Sochch no, but that's the talk showhere. Even though Fox picked it up for two seasons, Stepmar Mercury anytime can go, you know what, this ain't working for us. So it doesn't mean I'm guaranteed, but it shows that Fox had faith in my show, and the affiliates have faith in my show that they said we want to do two years with you.

What's your daylight? Now? What's it like on production day? Like today?

Production day, Well, after I take care of my son and get him off to school, I come in and seven in the morning, and I immediately have to get if there's anybody waiting, Some people fly in and they get there really early. I will sit and talk to them and take pictures. That's like five ten minutes. I'll take pictures with anybody that's out there, and then I come in. They start doing my makeup. But literally about seven forty five, I gotta go over hot topics because

I can't believe it. This is what and they said that was funny.

Then we go over all we find hot topics that we can talk about, and I look for stuff that I can bring a lightness to and a fun attitude and spirit too, like Jimmy Butler had a different.

Haircut and I was pretty freaky.

Yeah, this this latest morning, we went on this whole thing, and I said, oh my gosh, that would be funny because I know the coaches are telling their team just play on the side of his bangs.

He won't be able to see you.

And the jokes just started fine, and I said, this is gonna be a good day because stuff is coming to me right and I have So it was initially it was me writing my own jokes, but now we have a comic named Tammy Pescatelli, who is this amazing Italian woman ballsy, and so she will help me flesh out what I want to say.

It's great to have a partner, right, a collaborator. You go do it in music, you know, they collaborate with each other all the time, and they come up with these magical things that they would not have done on their own. Having a collaborator like your Tammy.

It's Tammy, and it's really important because I just got Tammy last week. But before that I had nobody. I was the only comic. So I wanted younger people to be in the room with me. Just tell me what are the cause you know, at my age, I don't look at everything. I'm not on social media all the time.

I'm like, I need to go.

You know, at this stage, this is when you keep hearing people say you got to go to sleep at eight. I go, what nobody told me that when I was in my twenties, Because in your twenties, you don't have to go to sleep at eight.

You can go to sleep at four party and then go to work.

Are you going to sleep at eight? Really? No?

Probably eleven friturday. You know, you lay down and you look at the ceiling. And I keep going what they say on TikTok and social media eight o'clock, I'm supposed to get into something called my circadian rhythm, but it ain't happening. So let me get on Instagram. But about eleven, so I'm in there. So I have young people in the room with me who can give me what therap and I go, what do you think about that as

What did they do before the Internet?

And I said to the young girls, I said, we had Encyclopedia Britannica, and they didn't laugh. They just looked at me, and I said, pull up a picture of the Encyclopedia Britannicas and one girl goes, that looks like Game of Thrones. It was so funny to me.

But wait a minute, what did we do before the internet?

We had there was a salesman that came to your door and sold you Encyclopedia Britannica, and that's how you did your book reports.

And here's the thing.

My family couldn't afford the whole set, so we only bought one letter a month because they were paying on this. So I never did any book reports that started with a T. That so we did that. And then when they got the children's edition of Encyclopedia Britannica, people thought you was rich when you got that. But my daddy worked three jobs, so we had the kids edition also, I said. So I started going through of what we did.

You know, they cigarettes, They knew everything about everything.

It was my uncle Earl who said at the barbershop that was Alexis. And so when I saw them laughing, and then I saw the little girl, the little young one say that those Britannicas look like the Game of Thrones, Right, I go, that's a great joke. And I said it, and everybody laughed. And so that's how I call my material.

So it keeps you young anyway, I mean, it keeps you plugging.

I have to hang around you because I do.

At this place where I have, everyone's younger than me. Of course, everyone's younger than me everywhere I go, probably, But no, the thing that's a gift for you, Sherry, is you get to keep learning. Yes, but you're you're forced to learn, But you get to keep learning, and you don't feel like you're just old and stale and living in a closet somewhere.

I think that people who don't young, And that's why I understand why a lot of times older men will get with younger women as opposed to women my agent. I know a lot of women will get on me when I say this but we come with older woman baggage.

Things don't impress us like it with a young girl.

Like I remember a guy came to me and he had gotten a car that the remote control rolled down the windows and the remote control started the car. And he came and he was like, Sherry, oh my god, look at this. And I go, I gotta be mw on my driveway and I got.

I got this range drover. That don't impress me.

But a young girl will be like, oh my god, that's so amazing. Let's take a drive down the beach. Wow, you got this is your house. I expect you, you know, And so it brings up I think younger people bring a freshness and an energy. Like if you get with me and you want to take me out about eleven o'clock, I'm getting sleepy. We're not going to another place cause

Now you got a younger.

Girl who's like, let's dance, let's do this. It's an energy. That's why you see these old guys and you like you, how many days you gonna party and freaking with this young girl. But here's the thing, you don't get some good conversation. But you know you're not gonna be able to sit there and go, oh my gosh when I was with doing so, because they're gonna look at you and go, who's that.

It's a trade off.

It's exciting for these old guys. They get to hang out at DA do things they can't do with the old age.

They've never done. Do you know they can ride a motorcycle. Let my man tell me he got a motorcycle. I'm gonna be like, if you don't stop acting dumb and get off that motorcycle and get that leaf blower and blow them leaves. Get off that damn motorcycle where you hurt your back?

Do you miss it? Though? Do you miss doing the clubs as a young girl? Did you do you miss those days at all?

Art wish I had the energy like I go to a club. I can go to a club and dance like once every six months and it's fun. But if I had to go to a club now, Elvis I'm like, what, it's the music, so damn.

Too old?

Yes, I'm too old.

Or when you go to restaurants, you like, can y'all turn on the lights like I'm trying to make a baby. Why I can't read my I can't read the biddle. I sound like my aunty or my mother. And I go and the kids just laugh at me. We'll be whenever they have a birthday party or whenever they get together. I go, you know, and I'm like, Auntie, I sit right in the corner. I don't move, and they all come over to me.

Come on, Aunty, Cherry, Miss Sherry, let's dance.

And I'm like, I'm fine. I'm fine because I'm be in the hills all day. My feet hurt, but I like to be around them because it does give you, like some vitality.

So look, I'm sure every every two weeks the agent gets your paycheck, they put it in your bank account. Everything's all cool. What other than a great job, people taking care of you, working with people you love, what do you get out of this? What are you getting out of this? Just for you?

From the time I was for I love making people laugh, like I loved seeing my mother smile, and I loved seeing my grandmother smile. I've always liked people to feel better, and I've always I just knew doing everything. I've always used to dream of having my own talk show when I used to watch them when I was little, and even doing stand up. I saw Andrew Dice Clay and Eddie Griffin. That's what made me want to get in

And we have so much going on in the world.

People need laughter. I'm not talking about I am very well versed in politics. I love talking politics, but I will not do it on my show because I am there.

I want you to feel good.

You can get politics from anybody, whatever side you're on.

That's our policy here too. We don't do it.

I'm not going to do it because everybody everybody can do it. What I am I'm here for is to make you feel better.

But you know what you're doing something else, Shery. I'm interrupting, but I look at the time, I want to get to some points. Here's the thing you do make people laugh. You do make people feel good. That's accomplished, done deal. But something else you do, and I kind of hit on this on our show, is you also make people want to make people laugh. You make people want to leave the room better that they found it in. It's

No, no, no, you're not.

I really mean that though.

But I think that's also in finding out and knowing who you are. Like I think that I just know that if I have a problem and I'm going through it, there's probably somebody in the audience that is going through the same thing. I when I say, you know my son is eighteen. So but when I talk about the fact that I'm just trying to navigate life with this son who's a teenager who doesn't even want to talk to me, there's somebody out there who's going through the

I and I you know, I like that.

I know, you know, I'm a celebrity and Shearry knows a lot of people, and she's probably making some money.

You know.

I don't like to say how much because I got two ex husbands I'm paying okay, But still I want you to feel like that I am dealing with the same thing that you are dealing with. So I like to tell people, and I think those stories make people feel like, Okay, I'm not crazy over here, and it's going to be okay if I get through it with the smile. There's something I want people to know that if you can find the silver lining just a little bit, that'll take you far.

Also, you know, you show such courage. This is not just you, but all of us. You're showing courage when you show vulnerability, right, And I know I love getting on the air. I love talking to people. I love asking how their day is and making them laugh whatever. And then a friend of mine once said, Elvis, are you doing this because you're trying to like heal yourself from something as a child? I said, I don't. Maybe, I don't know. Do we really have to get that

No, I don't go through that because I feel like, if anything, it's sometimes it's harder to be more vulnerable, because, you know, because you feel like you inspire so many people. I inspire people to be healthy to take this journey, So sometimes it's harder to go. I feil and I now I am hiding her. She's kisses in my shoes and in my dressing room, and because I feel like I'm now I'm letting people down because they're so inspired to go to the gym, and this is hard for

Because now I want a talk show.

It's a different level now that I can't just be vulnerable and do a live and go, oh my gosh.

I just feel like.

I don't feel good today because I know it will be on blogs and it will be on a TMZ, you know, if it's a slow news day and now it's bigger than what it was, you know, and so you lose a little bit of the So I can't work out healing. On TV, I will tell what happened to me and how I dealt with it, but I don't, and every once in a while I go, oh my gosh, I had to get this chocolate chip cookie.

But it's harder for me.

When I used to do Ellen Ellen, I held the record for being the most book guest on Ellen because she loved my When I was transparent, I would talk about celebrities I didn't care and Ellen loved it. And I remember she said, you can get away with that. People think I'm too nice. I can't say what you say, but I had nothing to lose, so I can say whatever. Now I understand what Ellen meant, because you know, now there's some things I can't say. The backlash I've experienced

I could care less.

But now I have a child, I have bills, a bag, I got ex husbands, I got parents.

I'm taking care.

You have too much to lose, So I'm not as I'm not as risky as I used to be. Right, but still within this I don't talk about relationships.

You know.

I have learned that I keep that part of my life private. So I just flirt with everybody, but you know, I don't talk. I've learned my relationships. I need something that's private, that is mine.

So you're not gonna start digging into a guest's relationships because you were sensitive.

Second, I am because I've been I've been on the other end where I've been on talk shows and all of a sudden, I go, I don't want to talk about this, and then they grab my hand and they go, we have to talk about this, and I'm like, I just got ambush. That's not right. And I know there's some a certain sector of people they want to hear that, but not for people who watch me because they know they're not going to get it with me.

I'm very and I'm in this world.

I am.

Yes, I'm relatable, but I've been in this business for a long time, so i know what that's like when somebody comes on the show and they don't want to talk about it. And I always tell people, we're gonna have fun, like you whatever you want to talk about, and people who like me will like our conversation. I don't do sialacious. I don't want to make people feel bad.

It's a divorce. Why is this your topic when it's my divorce. I get that. Yeah, but we're the same way with this show here. I don't want to make people feel uncomfortable. Every once in a while, when you're booking guests, they'll say, hey, can't wait to be on your show, but here's like three things we really don't want to talk about these. I'm like, fuck you, We're not going to talk about those anyway. I would never because I want people to want to come back.

You want people to come back.

You want to make it a place where it's like I tell you, when I started this show, we had to have parties with publicists and I had to let them know I want your people to have a good time. I want people to leave going. I want to come back to the show because if you're having a good time, the audience is going to have a good time. And people who want to come and see the salacious you got all kinds of so you.

Can go, they have other places to go for that.

You can go and get that.

And so I feel like, if you have fun, you'll want to come back and have fun with me. And that's how my show is going to And the day people don't want that anymore, I'm gonna go do something else.

Well, no time soon. Sherry Shepherd love having you here. Thank you. And when you walked out of that room today, you did change that room because everyone's like, God, I love her, did you? Andrew was there? Daniel's like, I love her. I just fucking love her. Matt Bronkshick, I fucking love her, oh Man, and then Gandhi love her. I mean you are loved. So keep sprinkling that magic.

God.

Thank you for y'all because y'all are so wonderful. And it's like you get excited. When they said you're going to Elvis's show.

I was so excited because it's just fun.

I know I'm going to see here somebody who's gonna hit me with the something and why I get uncomfortable and I gotta pivot.

NIC's just fun coming here.

We won't do that, Sherry Shepherd. Thank you very much.

Thank you.

So many things to live by in this episode, Sherry, we love you. One of our favorite points Sherry made by the way was that laughter really is the best medicine, no doubt. To know Sherry Shepherd is to love Sherry Shepherd, and we're so proud of her and all the success of her talk show Sherry, which you can watch every weekday. Just check your local listings, make sure you like, review and subscribe to Thinking out Loud wherever you get your podcasts.