
Wanda Sykes is one of Mike’s original dream guests for the podcast. Now, on the heels of her new Netflix special, Legacy, Wanda talks with Mike about how they both started in DC, and why Wanda left her job at the NSA to pursue a career in stand-up comedy. Wanda tells the story of how she moved from the writers' room of The Chris Rock Show to acting in sketches, how she got tricked into auditioning for Curb Your Enthusiasm, and the weird requests she gets from Curb fans. Plus, new jokes from Mike and Wanda.
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Mike Birbiglia
You've talked about in your special about all the hard things about getting older. But like, what's it, what's a surprisingly pleasant thing about getting older?
Wanda Sykes
Ooh, it's for me, when I say I don't want to do something, I just don't do it, you know? Sure, yeah. Right now it's like, no, I don't want to do that. I don't feel like I have to, you know, appease other people. I don't feel, yeah, I can, I can be, I can be more honest. And yeah.
Mike Birbiglia
That is the voice of the great Wanda Sykes. Wanda Sykes, everybody. She is a legend. I have wanted her to come on this podcast since we started it almost exactly six years ago. It was like I made a list of people who would be my dream guests for this show and she was like on the 10 or whatever and. And somehow six years later, we got her very excited. She, of course, is one of the great stand up comedians. She was one of the original writers on the Chris Rock show in the 90s. She and I both started out in D.C. talk about that today. We even work out some jokes as sort of a dream sequence of things that happen today. By the way, thanks to all the Working It Out Premium subscribers, it is building and building. Usually just came up with a new idea the other day called Suggestion Box. We're going to do an episode called Suggestion Box. If you email your audio voice recorded suggestion for the show, the thing that you're most critical about with, with Working it out, the thing you like and the thing you like most about the show and, and then what you would suggest we do differently. Email that to workingitoutpodmail.com and we're gonna have just an episode where we frankly discuss what could we do, what could we not do, what are our limitations and what are the possibilities. And then we're gonna put it out there for the Working It Up Premium subscribers. We just did one with my favorite improviser, Liz Allen. She was the improv coach for Don't Think Twice and we had a great one with her recently. That's over at Working It Out Premium. If you sign up on Apple Podcasts, it's 4.99amonth and you get no ads whenever you listen to the podcast. So if you hate ads, that is the service for you. By the way, you can watch the full episode of this podcast on YouTube. Oh, also the video is now on Spotify. That's a whole thing, apparently. So. So if you want to watch the video on Spotify, it's over there, too. And apparently coming soon on Apple Podcasts as well, the video. So stay tuned for all that. We're just doing the show. We will continue to do the show as best we can. And we're just going to try to roll with the punches of the various mega businesses at Apple and Spotify and all these places that. That are trying to. Clearly trying to monetize in, like, a zillion different ways that I'm sure doesn't benefit anyone except themselves. But we just love doing our show. That's the most important thing. We really appreciate you listening and watching. I'm really excited to bring this talk with Wanda Sykes to you today. We talk about her new special, which is called Legacy. It's on Netflix. We talk about her coming out of the closet many years ago. We talk about how before she did comedy, she worked at the nsa, of all places. Just a fascinating life story and incredible career. Enjoy my conversation with the great Wanda Sykes. I followed you for so long because I started as a door person in D.C. the Washington, D.C. improv. I remember because it was the late 90s. You used to come there.
Wanda Sykes
Yeah.
Mike Birbiglia
All the time. And you still stop in there.
Wanda Sykes
Yeah, yeah. That's where I. I go there when I'm just putting together an hour, you know, before I take it out on the. On the road. And then I. It's like my last stop before I shoot the special.
Mike Birbiglia
Yeah, yeah. There's something about that comedy room that is so. The alchemy of it is just works for comedy.
Wanda Sykes
Yeah.
Mike Birbiglia
And you can't even put your finger on it. No, because I remember, like, that's where I started. And then I would go, like, that was, like, the first place I played. I opened for. It was like 1997. I opened for Chappelle.
Wanda Sykes
Okay.
Mike Birbiglia
At that point, he was a headliner. He was like, 24. And I was like, 19. And I was like, oh, my God, this is gonna be great. I'm gonna be great. And then it's like. And then I went to other clubs. I'm like, oh, okay. It's not as good.
Wanda Sykes
It's not as good.
Mike Birbiglia
It's not as good as this.
Wanda Sykes
Exactly.
Mike Birbiglia
There's something about certain comedy rooms where you go, like, oh, it's friendly to comedians.
Wanda Sykes
And then you take a trip to, like, Roanoke.
Mike Birbiglia
Yes. And you're like, all right. Right. This is what it's like, too. Did you start in D.C. yeah, started in D.C. and at that time, like, I read a story. Where did you. Did you take Dave to, like, open mics? When he was, like, a teenager.
Wanda Sykes
Every now and then, right, when. If Dave's mom couldn't make it to the club, then he would ask me, he said, can you just, you know, say that you're my aunt and. And that, you know, like, you're my guardian tonight? And I was like, yeah, Dave, sure, whatever. And also I would give him rides home.
Mike Birbiglia
Oh, my gosh.
Wanda Sykes
Yeah. Cause he didn't at that time, he didn't live too far from me, which was weird.
Mike Birbiglia
So you started in D.C. like, Comedy Cafe Garvin's. What got you to do it? To, like, take the plunge into doing mics.
Wanda Sykes
It was so bizarre how I got into it, but basically I was bored. I was working for NSA at the time.
Mike Birbiglia
That's the interesting thing.
Wanda Sykes
I was working for NSA at the time, and I just felt like, this is not what I'm supposed to be doing, and I'm not gonna retire from this. I'm not gonna work here, you know, 20, 30 years and retire, and that's it. There's got to be more to it. And I think it was kys W ky. Well, they were having a. Some talent competition, whatever, and they said comedy was a category.
Mike Birbiglia
Yeah.
Wanda Sykes
So I just. I said, you know, I'm going to write some jokes and try it.
Mike Birbiglia
Yeah, I was just.
Wanda Sykes
Just that. Just naive and, you know, never been to a comedy club. Yeah, I've just, you know, watched comics on tv, but never been in the. In the room. And I wrote jokes and the guys was like, yeah, I'll put you on. And it went well. Tony woods won.
Mike Birbiglia
Oh, nice.
Wanda Sykes
Yeah, Tony woods won. But Legend. I did well. Yeah, I did well enough. And Andy Evans was hosting, and he. He was like, who are you and where.
Mike Birbiglia
Where are you from? Like this, like, the first time you did it.
Wanda Sykes
Yes, that was the first time he was. I haven't seen you in the clubs or anything. What's. What. Who are you? You know? And he then, you know, took me around to the clubs.
Mike Birbiglia
Yeah.
Wanda Sykes
Yeah. Took me to Comedy Cafe Garvin's. And that's when I found out that, oh, this could go horribly wrong.
Mike Birbiglia
Right. You know, totally right. Because every room is kind of different from each other.
Wanda Sykes
Right.
Mike Birbiglia
When did you have a sense of, like, how long did it take you to find your voice?
Wanda Sykes
Oh, God, probably right after my divorce. I was working at the Chris Rock Show.
Mike Birbiglia
Yeah.
Wanda Sykes
Actually writing on that. And so even then, I was still doing what I thought, you know, my idea of a. Of a comic. Right.
Mike Birbiglia
Sure.
Wanda Sykes
I think we all kind of Start out as doing either Seinfeld, Richard Prior, you know, whoever you're watching. Yeah. Whoever you're watching.
Mike Birbiglia
You.
Wanda Sykes
You kind of, like, morph into that person. But it wasn't until after that that I said, you know what, Bumper? What am I doing? I'm. I'm going to talk about what's really happening.
Mike Birbiglia
Yeah.
Wanda Sykes
In my life. Let me talk about. About me, you know?
Mike Birbiglia
Yeah. Yeah.
Wanda Sykes
So I was like, oh, let's talk about it.
Mike Birbiglia
It's one. I love your special, and it's refreshing that you're not going to the you can't say anything anymore trope that's in so many specials now.
Wanda Sykes
I don't get it.
Mike Birbiglia
It's so strange to me.
Wanda Sykes
Right. Because you can. You can.
Mike Birbiglia
Yeah. It's so odd. It's such a weird take.
Wanda Sykes
Yeah.
Mike Birbiglia
To be like. To say that on a platform that literally goes to hundreds of millions of people. And also, like, I have to say. And people could probably contradict me, but, like, I've never heard of Netflix even giving people a note. No, I've never heard of it.
Wanda Sykes
No.
Mike Birbiglia
And certainly not the people who are saying that.
Wanda Sykes
Right, Exactly.
Mike Birbiglia
Not those comments. Not saying shit.
Wanda Sykes
Not giving them notes at all.
Mike Birbiglia
No.
Wanda Sykes
I always. I go to the place of. Well, what is it that you want to say?
Mike Birbiglia
Right. What's that.
Wanda Sykes
What is that thing?
Mike Birbiglia
Yes. Yeah. Yeah.
Wanda Sykes
It must be quite awful. What? I'm like, just say it.
Mike Birbiglia
Just whisper my ear. Whisper in my ear, and then I'll tell you if it's.
Wanda Sykes
Write it down.
Mike Birbiglia
Write it down.
Wanda Sykes
Slip it to me, and. And I'm sure we will go. Oh, you can say that.
Mike Birbiglia
Yeah. I think you'll be all right. Yeah. Yeah.
Wanda Sykes
No big deal. Right.
Mike Birbiglia
You're in that great documentary, Outstanding on Netflix that's about gay and lesbian comedians and trans comedians. And you were in the closet and then you started talking about it and people told you not to.
Wanda Sykes
I don't think people told me not to. I think it was. I just wasn't ready.
Mike Birbiglia
Yeah.
Wanda Sykes
You know, I just. I just wasn't comfortable enough.
Mike Birbiglia
Yeah.
Wanda Sykes
I mean. Well, actually, I take that back. My mom did say, you know, don't talk about it.
Mike Birbiglia
Yeah.
Wanda Sykes
Yeah.
Mike Birbiglia
That was very much like my dad. Not with being gay, but a lot of things.
Wanda Sykes
A lot of things.
Mike Birbiglia
Yeah. Yeah.
Wanda Sykes
I'm sure there's other, you know, like, there's other things that my parents would probably be like, can you wait till we. Out of here? Of course. Before you talk about stuff.
Mike Birbiglia
Yeah.
Wanda Sykes
You know. Yeah. And you do that, you know, respect my respect. My family and I never want to give some. Give other people, especially people I don't know and don't care about information or just something where they can look at, you know, my family in a bad way. Because that's totally not the case. But you can see how people can know.
Mike Birbiglia
But that's not the goal.
Wanda Sykes
Exactly. Yeah, exactly.
Mike Birbiglia
So, no, that's how I, that was like my relationship with my dad. He never wanted me to be a comic. And it would, it was similar. It would just be like, don't talk about personal stuff. And, you know, after a certain point, I feel like in comedy you realize, like, you're not hiding anything from anybody. No. They can kind of tell what your whole deal is. But like, did your parents, would they come to your shows when you're starting out?
Wanda Sykes
They came to one.
Mike Birbiglia
Yeah.
Wanda Sykes
And I bombed silly. I never should have invited them because I just started out, I didn't know what I was doing. So, I mean, it was horrible, horrible bombing where people, like turned their chairs around, you know, D.C. people. It's. Yeah, sure. Sometimes they don't even have to boo. It's just the thing of. They're just annoyed with you, you know, like an old woman was like, oh, God. Just kind of turned her chair around. You're like, oh, okay. And I remember my mother going, don't worry about it. You have a good government job. You are good. Don't. You don't ever have to do this again. Don't worry about it.
Mike Birbiglia
Oh, my God.
Wanda Sykes
And she didn't know, like, this is. That you have to do this.
Mike Birbiglia
Yeah, yeah, yeah.
Wanda Sykes
This is the only thing I want to do. This is what I want to do.
Mike Birbiglia
That is something that's really funny about stand up is that when people don't like it, it is, it hurts so much. The thing you're describing, the physicality of people just kind of.
Wanda Sykes
Yeah.
Mike Birbiglia
It's so real to, to like speak your truth and have people turn around. There's nothing like that.
Wanda Sykes
No.
Mike Birbiglia
I think it's part of the reason why comedians are so tough.
Wanda Sykes
Right.
Mike Birbiglia
Like, we're tough skinned because we live through like these rejections that are like, you can't compare that to anything.
Wanda Sykes
But it hurts. It hurts. I mean, you, you can't sleep.
Mike Birbiglia
Yeah.
Wanda Sykes
Right. Your food tastes different.
Mike Birbiglia
Yeah.
Wanda Sykes
Just.
Mike Birbiglia
Your food tastes different. Yeah, yeah. No, it's your whole.
Wanda Sykes
Yeah, you get a good show.
Mike Birbiglia
Yes. You're always just waiting for the next good show. So you wrote for Chris Rock. Was that like you moved to New York and then was that your first writing job.
Wanda Sykes
Yes.
Mike Birbiglia
Wow.
Wanda Sykes
Yeah. Write real writing. That's huge. I know.
Mike Birbiglia
And do you get it from just cold submission? Do you know Chris.
Wanda Sykes
I opened for Chris when he. At Caroline's, and he was just about to shoot Bring the Pain.
Mike Birbiglia
Yeah.
Wanda Sykes
And he, you know, was like, hey, you're funny. I really, really like your stuff. I'm like, oh, wow. Thanks, Chris. He said, I might have something for you. I'm like, okay. And of course, you know, time passes and his special blows up and all. And eventually, I did get a call and said, hey, Chris would like for you to submit some writing samples. And I put together a packet and got the job.
Mike Birbiglia
Wow.
Wanda Sykes
Yeah.
Mike Birbiglia
What did you learn in being, like, in a writer's room?
Wanda Sykes
Everything.
Mike Birbiglia
Really.
Wanda Sykes
Everything I know about TV today, everything. And producing, I learned from being on the Chris Rock Show.
Mike Birbiglia
Wow.
Wanda Sykes
Yeah. Everything. Just, you know, writing bits, writing, you know, sketches, producing pieces and having all those things in mind as far as, like, locations and casting, editing. First time. I've never done editing.
Mike Birbiglia
You were on the show, too, right? Yeah. Cause I remember seeing you in sketches on the show.
Wanda Sykes
Right. That was by accident, I guess, just circumstance, because we had booked a crew to shoot other pieces, and the producer, being a good producer, was like, hey, we have four hours left on the crew. You guys have anything? Anything we can shoot quickly, like in the office we need. And two of the guys, they wrote a bit video Mama, where it's, you know, you put a videotape in and it's someone watching your kids for you on tape. So it was like, wanda, you do it. And I'm like, I. I'm not in front of the camera. Said, no, come on, do it, do it. And it was just me, you know, going, put that down. You know, hey, where are you going? Get back here. You know, it was just me yelling at kids, watching tv.
Mike Birbiglia
Wow.
Wanda Sykes
And that's when they said, okay, we're gonna put her in more. More stuff. Yeah.
Mike Birbiglia
What do you think is, like, the best quality of, like, a writer in a writer's room?
Wanda Sykes
I think, being able to listen and just don't say no. Have a fix for it, you know, like, if you're not getting anywhere, if it's. You just keep saying no, Right. If you're trying to, you know, a joke or a bit. And if I don't get it, I'm going to ask you, what is it that you're trying to do? What's the thing? Right. Tell me what. You know, what's the. What's the thing? What's the bit. Right. And then I can help get you to where that bit is where kind of makes. Makes sense, you know, But. And that's the thing that I learned.
Mike Birbiglia
Yeah.
Wanda Sykes
Being in there, because it was very collaborative. You know, Chris would come in and say, you know, I think we should have more of this in this bit. And it's like, okay. Why? Okay, I get it. All right.
Mike Birbiglia
Yeah.
Wanda Sykes
How about we try it this way?
Mike Birbiglia
Yeah.
Wanda Sykes
You know. Yeah.
Mike Birbiglia
One of the things that sticks out about your career is, like, you've been successful in comedy for so long. And, like, you know, I've been in comedy, like, 27 years, and, like, you see people drop out. You know, you've probably seen tons of your peers just drop out, and it's like, what do you think is part of the endurance of people in comedy who are able to do it so
Wanda Sykes
long and so well, other than just sticking with it, but also take some risk.
Mike Birbiglia
Yeah.
Wanda Sykes
You know, write.
Mike Birbiglia
Yeah.
Wanda Sykes
New jokes. A lot of people, they just. I don't know, they just got so comfortable. And that 30 minutes or whatever hour that works.
Mike Birbiglia
Yeah.
Wanda Sykes
And it's like, okay, let's. Let's. Let's. Some growth here.
Mike Birbiglia
Yeah.
Wanda Sykes
I like to think that. That there's. That there's growth and that my fan base can see that they're along for the ride. Yeah, yeah, yeah, yeah.
Mike Birbiglia
It's interesting. Like, I feel like since the 2000s, it's like a different era in comedy than it was like in, you know, the 80s. Like, Seinfeld would talk about how, like, people would have an hour and they would just tour right with it for 20 years and just hone this hour. And it's like, probably around 2,000 or so, it started to be like, no, no. What's your next hour?
Wanda Sykes
Right.
Mike Birbiglia
And it really put a pressure on us, but as comics. But in some ways, it's good. It's good. It's exactly what you're saying. It's good to turn over another hour. Like, what else are you thinking about?
Wanda Sykes
Jay Leno would always tell me. He was like, you guys, I don't understand it. Why shoot an hour? Because, you know, you could just live on that forever.
Mike Birbiglia
Why are you doing.
Wanda Sykes
I was like, it just doesn't enter that. That's not what. What fuels me. I. You know, that's not my drive to keep telling the same joke every now and then. You know, like, for me, once I shoot an hour, that. That material's done, I'm. I'm. I gotta.
Mike Birbiglia
Yeah.
Wanda Sykes
I need new stuff now.
Mike Birbiglia
Yeah, you've talked about in your special about all the hard things about getting older. But, like, what's it. What's a surprisingly pleasant thing about getting older?
Wanda Sykes
Ooh, it's for me, when I say I don't want to do something, I just don't do it, you know? Sure. Yeah. Right now it's like, no, I don't want. I don't want to do that. I don't feel like I have to, you know, appease other people. I don't. I can. I can be. I can be more honest. And, yeah, I've lost that. You know, that. That fomo.
Mike Birbiglia
Yeah.
Wanda Sykes
I don't. Nah, I don't need to go.
Mike Birbiglia
Yeah. I love the line from your special, the only time white women work together is synchronized swimming. Does a line like that come to you, or are you always, like, walking around with a notebook? Like, how. How do you. How do things, like, germinate?
Wanda Sykes
Oh, a lot of good lines. Just. Just things. They just come to me sometimes to the point where I'll call someone and say, hey, have you heard this before?
Mike Birbiglia
Yeah, yeah, yeah.
Wanda Sykes
Because it just came to me so easily. Keith Robinson. I do that a lot with him.
Mike Birbiglia
Yeah.
Wanda Sykes
I'll call him. Hey, man. Does this. And he's like, no, I haven't. I hate. And I hate that you thought of it.
Mike Birbiglia
I hate that you thought of that. He's immediately resentful.
Wanda Sykes
Immediately.
Mike Birbiglia
You've been friends with Keith forever.
Wanda Sykes
Forever. Yeah, forever. I've known Keith since 87. 88. He was the one, like, my first comedy friend, other than, you know. You meet him in Philly Evans? No, I met him. He was in D.C. a group of Philly comedies came to.
Mike Birbiglia
Oh, no kidding.
Wanda Sykes
D.C. and, yeah, he tried to hit on me.
Mike Birbiglia
Sure. Sure he is. He's one of those people. If people haven't seen his Netflix, recent Netflix special is so good.
Wanda Sykes
So good.
Mike Birbiglia
He is funnier by the year and two strokes into his life. And it's painful to admit that he is funnier because he gives everyone else so much shit.
Wanda Sykes
Yep.
Mike Birbiglia
That it's hard to give him a compliment, but he is. He's unbelievable.
Wanda Sykes
Yes.
Mike Birbiglia
You're talking. You're special about how your wife hates when you're at the casino. Cause you track each other.
Wanda Sykes
Yeah. No, no, no. She tracks me.
Mike Birbiglia
Oh, she don't track her.
Wanda Sykes
I don't. I don't. I don't track her.
Mike Birbiglia
Oh, interesting.
Wanda Sykes
Yeah.
Mike Birbiglia
So she. So she doesn't like it when you're at the casino. Why? Why wouldn't you like you at the casino?
Wanda Sykes
Oh, I'm not good in the casino. You're bad. Oh, my.
Mike Birbiglia
You lose a lot of money?
Wanda Sykes
Not a lot of money. Yeah, I mean, I don't. I don't lose a lot of money like, where I'm not, you know, in church on Sunday. Go. I'm a little short this Sunday, guys.
Mike Birbiglia
Yeah.
Wanda Sykes
Hey, the book says the split aces, you know, we know how you feel about book and follow the book. No, it's not that bad. But I do. I enjoy it. It's fun. Cause, you know, when I'm in there, I shut everything off.
Mike Birbiglia
Yes.
Wanda Sykes
Yeah. You're just looking at those little wheels go around, or you just wait for the next car. It's all the lights and noise. So to me, it's a great distraction and stress relief. Right.
Mike Birbiglia
What was it? What's your favorite and least favorite thing about improvising with Larry David on Curb?
Wanda Sykes
My favorite thing was when I could crack him up. Yeah, that was the best.
Mike Birbiglia
Yeah, that laugh.
Wanda Sykes
I would love just watching him lose it or try not to, you know, lose it and try. Yeah, Just breaking him was. Was, like, the best for me. What was the most stressful was, you know, he would never give me the storyline.
Mike Birbiglia
Oh, really?
Wanda Sykes
No. I know other people got to see the. You know, I didn't get the outline. All I got was whatever information he needed for me to say in that particular scene. So I had no idea what the episode was. So he would say, okay, all I need you to say in this scene is you got this perfume from. Or Cheryl had to pick up this perfume from someplace.
Mike Birbiglia
Yeah.
Wanda Sykes
So just, like, little story points. But then we would just. We would just riff, you know, just improv and get me. It's Larry David. I wanted.
Mike Birbiglia
Of course. You want to be great.
Wanda Sykes
I want to be great.
Mike Birbiglia
Yeah.
Wanda Sykes
Right. So that was stressful, but. But for me, just. Yeah, breaking him was the best.
Mike Birbiglia
How did you end up on the show? Did you audition for the show or he just thought of you?
Wanda Sykes
I was friends. I'm friends with one of the producers at the time. Sandy was a producer on the show. Sandy produced some of Chris's specials, so that's how. While she was around, so. And we talked about how much we loved the show Curb. And she said, you'd be great on the show. Yeah, you should come over and audition. I was like, I can't audition. I was like, I'm the worst at auditioning. I never get anything that I'll audition for. It's just. I can't do it. And she's like, okay. Well, she said, well, you got to meet Larry one day. I said, I would love to meet him, but. So she called me up. She said, hey, we're shooting around the corner at this. At this car dealership, Toyota dealership. Come over and you can meet Larry.
Mike Birbiglia
Yeah.
Wanda Sykes
And I was like, just. I'm just gonna come to meet him. She said, yeah, yeah, yeah. Just. Just to meet him. Don't worry about it. So I get over there, and there's, like, five black women sitting in the. You know, in the dealership. I'm like, are they just giving. Giving away Toyotas to the sisters today? I mean, is it a sale? You know? And she's like, no, no, just don't. Don't worry about them. Just. Just come on in. So I walk in, and Larry goes, hey, I know that tush anywhere. And I was like, excuse me. What? You know, and it turned into. We were. It was an audition.
Mike Birbiglia
That's ridiculous.
Wanda Sykes
Yeah. And he goes, yeah, this is who we're going with.
Mike Birbiglia
Absurd story.
Wanda Sykes
This is who we're going with. Yeah.
Mike Birbiglia
You got tricked into auditioning.
Wanda Sykes
Tricked into auditioning.
Mike Birbiglia
Who gets tricked into auditioning? I've never heard of that ever.
Wanda Sykes
Right here.
Mike Birbiglia
That's wild.
Wanda Sykes
Yeah. And I'm. I'm grateful that she did that.
Mike Birbiglia
Do people think because your character is, like, outgoing on that show that you'll be like that in life? Like, do people expect that from you?
Wanda Sykes
Yes.
Mike Birbiglia
Do you find. Are you disappointing to people?
Wanda Sykes
Yes. Yeah.
Mike Birbiglia
You have to explain that to people. Like, I'm not.
Wanda Sykes
Like, I'm not crazy like that. That's. Yeah, yeah. So many times in the airport. I get it all the time in the airport. Hey, Wanda, cuss me out or, you know, come on, say something. Be mean to me. I'm like, why? I don't know you? Or they on the phone, hey, it's my dad. Call him a motherfucker. Say something like, I don't know your father. And then they end up kind of getting it out of me because I get pissed that you're asking me this. I'm like, what the hell is wrong with y'?
Mike Birbiglia
All?
Wanda Sykes
And that, you know? So they get a little bit of it, but it's not intentional.
Mike Birbiglia
You know, when you do political stuff, do you ever find it splits the room when you tour?
Wanda Sykes
Oh, sure.
Mike Birbiglia
Yeah.
Wanda Sykes
Yeah.
Mike Birbiglia
Do you like it. Do you like it when a joke splits the room?
Wanda Sykes
I do. Because you know what you're getting when you come to my show?
Mike Birbiglia
Yeah.
Wanda Sykes
You know what you're in for?
Mike Birbiglia
Of course.
Wanda Sykes
Right. So it Wouldn't split the room, but let's say a little chunk. You can hear, you know, a few people getting disgruntled and.
Mike Birbiglia
Yes.
Wanda Sykes
Like, come on, enough of the politics.
Mike Birbiglia
Sure.
Wanda Sykes
And that's. That really annoys me when they feel like they can bully me. You know, it's like you're doing the exact thing that we're, you know, up in arms about. You're. You're. Now you're going to tell me what I try to dictate what I can do on my show.
Mike Birbiglia
Right.
Wanda Sykes
You know, it's the whole, like, what I like, supersedes what you, Your, you know, your desires. It's. Yeah, it's that it is.
Mike Birbiglia
Do you find. Because you've been doing political stuff for a long time, do you find the reaction politically is more polarizing than it was 20 years ago with crowds?
Wanda Sykes
Yes. Now it is.
Mike Birbiglia
Yeah.
Wanda Sykes
Before, you could make jokes, but you could laugh at yourself. You know, like, I could do jokes about something on the Right. And all right. You know, they might not be like, okay, that's a good joke. Yeah, totally not gonna. But okay, they're okay with it. And the same thing, I would make jokes, you know, I did jokes about Obama and people, you know, laugh, whatever. But now it is. It's different. They are just. If they're in, they're in. They, you know, MAGA doesn't find anything funny about, you know, maga. They're serious.
Mike Birbiglia
No, yeah, yeah. They seem very serious. Do you think there's gonna be like a break of this thing? Does the fever ever break?
Wanda Sykes
Don't know.
Mike Birbiglia
The fear. You know what I mean?
Wanda Sykes
Yeah, exactly.
Mike Birbiglia
Like, because I. That's how I feel. Like, I used to. I remember, like, in the 2000s, like, I would do every now and then I would do like a George Bush joke about the Iraq war or whatever it was. And you could get people, right. You could. You could get people in. In the south or the Midwest and. And it's exactly what you were describing. They would give you this look, like, I don't agree with you, but that's pretty funny. What are you going to do? That's. Right now it's like, you don't get a lot of that look anymore. No, no, it's like, yeah, there is a thing, but I think it breaks at some point.
Wanda Sykes
I don't know. I think they are so in it that it's hard to come to come out of it. Because then now you're gonna have to admit that you, you know, made a
Mike Birbiglia
mistake for a lot a Lot. A lot of years. That's true.
Wanda Sykes
You gotta admit that I. That you were duped. That you fell for it.
Mike Birbiglia
Right. But then maybe. Maybe someone else wins in 28. And then it just becomes the kind of. Thou not speaketh of that one thing culturally. You know what I mean? And then we go, okay, that was a thing.
Wanda Sykes
No, we have to. Not only do we have to speak about it.
Mike Birbiglia
Right.
Wanda Sykes
It needs investigated.
Mike Birbiglia
Right. We gotta reverse the corruption.
Wanda Sykes
Yeah, exactly.
Mike Birbiglia
Cause you have to undo the corruption.
Wanda Sykes
Cause we can't be back in this situation again.
Mike Birbiglia
Wanda, I need you. Just for the good of the country, I need you to get involved and fix a lot of this stuff.
Wanda Sykes
I gotta fix a lot. I think you know what it is? It's not. It's all of us. All of us have to. To me, that's the only way to fix this. It has to be. It can't come from one group.
Mike Birbiglia
Yeah.
Wanda Sykes
It has to be a diverse group of us.
Mike Birbiglia
Yeah.
Wanda Sykes
To fix it.
Mike Birbiglia
Do you feel optimistic about that?
Wanda Sykes
We have to, right?
Mike Birbiglia
No, no. I get it, yo.
Wanda Sykes
For real, man. Cause if.
Mike Birbiglia
No, I get it.
Wanda Sykes
If. Cause if not, I'm just gonna go back to the casino and just. I'm all in. I'm gonna get this shit right. Yeah. What about my college education? Your eye?
Mike Birbiglia
Who?
Wanda Sykes
You're not going to. I'm betting it all.
Mike Birbiglia
Support for Working it out comes from article. You know, it's getting nice out. And article, man, they have really good deck furniture. My favorite place to be is the deck. Oh, the deck. Any deck. I got this really nice outdoor swivel chair at Article. I highly recommend it. Super comfy. I love this article furniture. They have a thoughtful design approach that makes it incredibly easy to mix and match, helping you create a space that feels cohesive as well as stylish. I feel like if you went on the Article website, you could spend hours there. With Article's 30 day satisfaction guarantee, you can shop with confidence, knowing that if you're not completely in love with your new furniture, you can easily return it. The peace of mind ensures that you can invest in your home without hesitation. By the way, Article is offering our listeners $50 off your first purchase of $100 or more. To claim, visit Article.comWIO and the discount will be automatically applied at checkout. That's article.com wio for $50 off your first purchase of $100 or more. Support for Working it out comes from Quince. Summer always changes how I get dressed. I don't know about you, but I go from super sloppy to mostly sloppy. But the truth is, joking aside, I want pieces that feel lighter and more breathable. Who doesn't? Things that are easy but also put together. That's why I keep coming back to Quince. Here's what I'll say about Quince. This is not in the copy. This is not what they're demanding. I do. I'm offering this. I don't think a lot about my clothes. This is my truth. This is my truth. But I ordered a few things on quints and I really enjoy wearing them. And they're like comfy sweaters, comfy shirts, like comfy basic things. And. And. And they're just not that expensive. And I think it's a really good site. Elevate your summer wardrobe. Go to quince.com for free shipping on your order and 365 day returns. Now available in Canada, too. That's Q-U-I-N-C-E.com for free shipping and 365 day returns. Quince.com. I love this quote that you had, which is you said, if you're passionate about your work, it makes the people around you want to be involved too. When did you. What project do you feel that way about?
Wanda Sykes
For me, what helped me was when I. When I shot this movie, this drama, I just did undercard, just from the director, Tameka Miller. Her passion about the project and all the. I mean, the effort that she put into it, the preparation, I mean, she had, you know, the storyboards, and she just knew exactly how she wanted this thing to look and how she would pour into me as far as, you know, the confidence that she had in me that I could. I could, you know, pull this off. And then going into the. It's a boxing movie, so I had to train and get into boxing. Right? And then being in that environment, I. It's like, wow, these people are really into boxing. You know, like, they. And just that energy. I was like this. Then this makes me want to, you know, seriously get into it and take it seriously. And I found a love for it also, you know, or I got headgear and shit.
Mike Birbiglia
Wow. It's crazy.
Wanda Sykes
Yeah.
Mike Birbiglia
No kidding.
Wanda Sykes
And that's far. Yeah. I love it. I love it. Yeah. And then, you know, we go to set and we start filming this movie. The crew. The crew, they were into it. I've never seen a crew just so passionate and wanting to get the job done and, you know, you know, cruise crews, you know, they. Hanging around sometimes or. But everyone. I did not see anyone like, standing still.
Mike Birbiglia
It was.
Wanda Sykes
Everybody was just so behind it. So I was like, okay, now I. I'm. It made me better.
Mike Birbiglia
Do you feel like. Because at this point, like, you've acted in so many things, it's like. Do you feel like all that, like, spills back into your stand up?
Wanda Sykes
Yes. Yeah, yeah. I'm way, I mean, aware. Way more awareness of, like, really trying to bring the bit or the story to life. Yeah, I'm way more animated now, you know, way more like in physical comedy, because it's just now I'm seeing it and I know what I want the audience to see or the world I'm trying to set for them. So, yeah, it definitely does help.
Mike Birbiglia
That was like one of the best pieces of advice I got when I was starting out at the door at the DC Improv, where I opened for Jake Johansson once. And he goes like, sometimes if a bit's not working, it's like you have a thing in your head and they just don't. You're not able to convey it.
Wanda Sykes
Right.
Mike Birbiglia
So it's like, try a different way, try a different word, try a different physicality. And that really stuck with me. Who are you jealous of?
Wanda Sykes
Who am I jealous of? Ooh.
Mike Birbiglia
Oh,
Wanda Sykes
that's a good one.
Mike Birbiglia
The follow up question is, who are you jealous of that you thought of but didn't say?
Wanda Sykes
Ah, you know, it's not jealous. It's not a jealousy. I think it's more envy. Jane Fonda is a pretty incredible person.
Mike Birbiglia
Yes. Impressive.
Wanda Sykes
He's an impressive woman.
Mike Birbiglia
Yeah, she.
Wanda Sykes
And the thing I love about her is she's constantly trying to be better. I mean, I'm like, damn, Jane, you're what? Like a. You're already 100. I don't know how, but, you know, you're good.
Mike Birbiglia
You know, like, take a break. Yeah. She's done a lot.
Wanda Sykes
She's done so much, but she's always, like, looking for the next thing or trying to educate herself in another, you know, space or whatever. So I.
Mike Birbiglia
She's also.
Wanda Sykes
I don't know if I had that kind of energy.
Mike Birbiglia
She's also sort of lived a thousand lives.
Wanda Sykes
Yeah.
Mike Birbiglia
Like so many.
Wanda Sykes
She will reinvent herself.
Mike Birbiglia
Yeah. What's something that you believed 10 years ago that you don't believe now?
Wanda Sykes
Well, I mean, yeah, I didn't. I really didn't believe that. That we could go this far, that people would be this. You know, I just. I believe that people love the country more than what I'm seeing now.
Mike Birbiglia
Right.
Wanda Sykes
You know, I thought people. I thought There was enough people who will put country first. Right.
Mike Birbiglia
Like, that they believed in the principles of the country and not the kind of cult of the country.
Wanda Sykes
Right. Yeah, absolutely.
Mike Birbiglia
Yeah.
Wanda Sykes
Yeah. What.
Mike Birbiglia
What about, like, because you. The special is at your college. Talk about how you used to sit in those seats.
Wanda Sykes
Yeah.
Mike Birbiglia
And it's like, what do you think you feel. What do you think differently from when you were sitting in those seats at your college?
Wanda Sykes
Well, from sitting at. Sitting in those seats. I. I didn't imagine that I could, you know, that I would have been performing on that stage.
Mike Birbiglia
Yeah.
Wanda Sykes
Never. Not. Wouldn't have managed imagine that. Because I grew up in such a traditional, you know, upbringing and, you know, my dad was in military and, you know, so I didn't. I didn't know anyone who was in show business, you know.
Mike Birbiglia
Yeah.
Wanda Sykes
So. Yeah. And I didn't think that happens. You know, you would think that that only happens out in LA or New York.
Mike Birbiglia
Sure.
Wanda Sykes
You know.
Mike Birbiglia
No, I found that to be. I grew up in central Massachusetts and I. Yeah. Similar. I didn't know anyone in show business. It was. It was even strange moving to New York or even, like, going to the DC Improv for the first time ago. Oh, my God, that's Dave Chappelle. That's, you know, Jake Johansson. Like, these are people I see on Letterman.
Wanda Sykes
Yeah.
Mike Birbiglia
Yeah. It's so odd, even just that. Yeah. Making that change from, like, watching this thing from afar to being like. Yeah, I could do that.
Wanda Sykes
Right.
Mike Birbiglia
Very.
Wanda Sykes
The audacity. Right.
Mike Birbiglia
The audacity.
Wanda Sykes
Think that we could do that.
Mike Birbiglia
The delusion of it. Yeah. That I should be doing that.
Wanda Sykes
Right.
Mike Birbiglia
What's the best piece of advice someone's given you that you used?
Wanda Sykes
I would say Chris Rock gave me the advice to make your special. Special. Don't get up and do a set. Make it special. And I've.
Mike Birbiglia
Yeah, that's really nice.
Wanda Sykes
Always use that.
Mike Birbiglia
Yeah. Can you remember a time in your life when you were an inauthentic version of yourself?
Wanda Sykes
Probably was when I, you know, was closeted.
Mike Birbiglia
Yeah.
Wanda Sykes
I would say. Yeah. Although I wasn't on stage saying about, oh, I love men or anything. I just wasn't talking about it.
Mike Birbiglia
Right.
Wanda Sykes
Although there was some things I, you know, probably wanted to talk about, but just. I just wasn't ready. So I guess that's still not being. That's still being authentic because I just. I wasn't ready. Right, right. I was still being me.
Mike Birbiglia
You have that great joke. Men are people. Go, men are dogs. No, they're not. Dogs are loyal.
Wanda Sykes
Yeah.
Mike Birbiglia
Wait did you come out in your comedy career, like, after you had started doing standup?
Wanda Sykes
Yes, it was the Imma Be Me special.
Mike Birbiglia
Yeah.
Wanda Sykes
That's when I really started talking about it. Yeah.
Mike Birbiglia
Was it a lot when. When you talked about it on stage for the first time? Because very few people have that experience of coming out.
Wanda Sykes
No, I felt good because I came out at the. As a rally. It was the Prop 8, the protest, the National Day of Protest because Prop 8 passed. And that's where I came out at a rally, and I was like, oh, well, I'm out, so might as well talk about it on stage now.
Mike Birbiglia
Wow.
Wanda Sykes
Yeah.
Mike Birbiglia
Is there any material that you have that you're thinking about for your next special that you haven't? That. That's early.
Wanda Sykes
Oh.
Mike Birbiglia
Like any seed of anything.
Wanda Sykes
I did think of something yesterday. I don't even know if this is a bit yet, but I wrote down, I would crush being white.
Mike Birbiglia
That's funny.
Wanda Sykes
You know, like, sure. I was like, I don't understand being white. You should be crushing it. Like. Like, oh, man, I would kill it.
Mike Birbiglia
Yeah, sure.
Wanda Sykes
I mean, really, Like, I could be president.
Mike Birbiglia
Yeah.
Wanda Sykes
I would kill it.
Mike Birbiglia
I would be that good. Of course you would.
Wanda Sykes
Boy, it depends on how, you know. Then I thought about how I want to use it, but I want to be, you know, be that white where I go and try to be, you know, great for everyone and make life good for everyone.
Mike Birbiglia
Yeah.
Wanda Sykes
But then again, it probably feels good to be just selfish and just, you know, just be me, me, me. Kill it.
Mike Birbiglia
Yeah.
Wanda Sykes
I don't know.
Mike Birbiglia
I had a similar train of thought the other day about how if you're a white man and you're not succeeding during the Trump administration, then something's wrong. Something's wrong. The pit boss is. The pit boss is pushing it all in your favor. They're looking away while you're cheating. I mean, like, everything is working in your favor. These are. These are winning conditions.
Wanda Sykes
Yeah.
Mike Birbiglia
The refs. The refs are looking away.
Wanda Sykes
Looking away. Not calling any fouls. You're good.
Mike Birbiglia
I wrote down this thing the other day. I had this memory that I jotted down, which is when I was a kid, we never had a gun. But one time my dad said to me, he goes, I was out to dinner with my friend Roy, and we decided that we were going to buy guns, and if either of us is ever in a vegetative state, we're going to promise to kill the other person. And. And then he goes, what do you think of that idea? And I was thinking I'm 12 years old. I'm mostly thinking about whether we're going to have gym class Friday and whether I should bring my shorts to school or whether I should wear my shorts under my school clothes and then take off my school clothes when we go to gym and put them back on. But yeah, I think you and your friend Roy should kill each other if that happens.
Wanda Sykes
Oh, that's great.
Mike Birbiglia
You know how sometimes you just have a, just like a random flash from childhood and you go, that's gotta be something, right?
Wanda Sykes
Yeah.
Mike Birbiglia
Tell me this, how do you work out? New jokes? Do you go to clubs?
Wanda Sykes
Yeah, yeah, yeah.
Mike Birbiglia
Where do you go?
Wanda Sykes
I started in a club, you know, actually out in la. My friend Bruce Daniels, he has this show drunk on stage and it's this little dive bar. Oh, that's fun act bar. And there's a, he has a room on Tuesday nights. So I'll pop in there and do like 15 minutes.
Mike Birbiglia
Fantastic.
Wanda Sykes
Or you know, I haven't been in the city in a while but you know, I would go to the Comedy Cellar and a lot of times I would just book a weekend so I can get, you know, at least four or five swings at it.
Mike Birbiglia
Yeah.
Wanda Sykes
And just work it out.
Mike Birbiglia
Yeah, work it out. Working it out is supported by Helix. Helix makes award winning sleep products tested and reviewed by experts like Forbes and Wired. Helix offers a 120 night sleep trial and limited lifetime warranty. 120 nights. I've been a Helix customer myself for many years, since the beginning of this podcast almost six years ago. Everyone on the staff here at Working it out has a Helix mattress. We all really love them. And Helix makes the best mattress I've ever slept on. And I've slept on a lot of mattresses. I travel quite a bit, stay in a lot of hotels. Traveling actually can be hard. If I could bring my Helix mattress with me on tour, I would. You can also rest easy with seamless returns and exchanges. The Happy with Helix guarantee offers a risk free customer first experience designed to ensure you're completely satisfied with your new Mattress. Go to helixsleep.com for 20% off sitewide. That sleep.com/bigs for 20% off site wide. Helixsleep.com support for working out comes from Warby Parker. It's summertime. Do you need sunglasses? Check out Warby Parker. I knew it. I knew it. Great selection of sunglasses. Prescription glasses start at just 95. Am I reading this correctly? That's for the frame and the lenses. I know you're probably thinking, what's the catch are $95 glasses any good? Have you ever looked through a Warby Parker window when you're walk walking around your neighborhood? They look amazing. Warby Parker has an amazing virtual try on. You can try their glasses on in the comfort of your own home. It's actually wild how well the virtual try on works. You can do it any time of day. Let's say it's 3am you can't sleep because you're stressed out about getting new glasses. Try them on right at 3am right in your apartment right now. Buy one pair of glasses and get 20% off any additional pairs at warbyparker.com that's 20% off any additional pairs when you purchase one pair at Warb B Y P A R K E R.com Prabygs warbyparker.com Prabygs support for working it out comes from NOCD. NOCD is the world's leading provider of OCD treatment. It's covered by insurance for over 138 million Americans. All their licensed therapists specialize in ERP therapy and will help you learn to take the power away from intrusive thoughts in live face to face virtual sessions. They also provide support between sessions when you need it most so you're never facing OCD alone. For some people, a what if isn't just a passing thought, it's a loop that you can't even get out of. And no matter what you do to try to feel better, reassuring yourself, replaying, researching the thought just keeps coming back. That can actually be ocd, not the organizing stereotype. Real OCD is persistent, unwanted, intrusive thoughts that feel totally out of character, along with mental or physical behaviors that you feel driven to do to get relief. These thoughts can be very real, which is what makes them so upsetting. So if you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started. Learn.nocd.com Mike. The final thing we do is working it out for a cause. If there's a nonprofit you like to contribute to, we will link to the them in the show notes and I'll contribute to them. The Ruth Ellis Center Ruth Ellis Center.org Named in honor of a resilient Detroit icon, Ruth Ellis, the Ruth Ellis center works to create a supportive environment and community for LGBTQ plus young people. Well that's awesome. We will contribute. We'll link to them in the show notes. Wanda Sykes Such an honor. It's so great to meet you And I've just loved your comedy for so long. Thanks man.
Wanda Sykes
Mutual. Appreciate it.
Mike Birbiglia
Working It Out. Cause it's not done. Working it out. That's gonna do it. For another episode of Working it out, you can follow Wanda Sykes on Instagram. Amwanda Sykes, her special legacy is on Netflix. Her movie Undercard, which we talked about, is available to rent on VOD. Check out burbigs.com to sign up for my mailing list. And even better than that, you can text Burbiggs to 917-444-7150 to get text message alerts about various sort of pop up shows. I just did one recently at the Comedy Studio in Hartford Square which was super fun. Our producers of Working it out are myself, along with Peter Salomone, Joseph Birbiglia, Mabel Lewis and Gary Simon. Sound mix by Ben Cruz. Supervising engineer Kate Balinsky. Special thanks as always to Jack Antonoff and Bleachers for their music. Special thanks as always to my wife, the poet J. Hope Stein and our daughter Una who built the original radio fort made of pillows. Thanks most of all to you who are listening. If you enjoy this show, please rate us and review us on Apple Podcasts. It really helps us out. As I always say, tell your friends, tell your enemies, tell your boss of the nsa. Just say hey. While I'm at work dealing with all this top secret information, I usually listen to this podcast called Mike Birbiglies Working It Out. It's where Mike Birigley. It talks about the creative process with other comedians and writers. Nothing top secret there, but important nonetheless. Actually might give you a breather from all the tension created from this top secret environment. Thanks everybody. We're working it out. We'll see you next time.
Release date: June 15, 2026
Host: Mike Birbiglia
Guest: Wanda Sykes
In this milestone episode, Mike Birbiglia sits down with comedy legend Wanda Sykes, his self-described “dream guest,” for a wide-ranging, honest, and hilarious exchange. The conversation covers Wanda’s comedy roots in D.C., her time at the NSA, her journey to authenticity—including coming out as gay in both life and comedy—her writing career, and the art and endurance of stand-up. They also work out new joke ideas and reflect on changes in comedy, politics, and personal growth. The tone is warm, witty, and candid, peppered with anecdotes and practical advice for creators.
Early Stand-Up Path:
Giving Teenage Dave Chappelle a Ride:
Transition from NSA Analyst to Stand-Up:
Getting Hired:
Learning TV Writing:
Transition to On-Screen Performer:
Advice for Writers’ Rooms:
On Line-Generating:
Longtime Collaborations/Friendships:
Splitting the Room:
Polarization Over Time:
Restoring American Values:
Acting Influences Stand-Up:
On Conveying Bits Effectively:
On Envy and Admiration:
Shifting Perspectives:
Returning to Her College for Special:
Best Advice from Chris Rock:
“Your food tastes different [after bombing].”
— Wanda Sykes, on recovering from a bad set ([13:17])
“Make your special…special. Don’t get up and do a set. Make it special.”
— Chris Rock’s advice to Wanda ([40:18])
“If you’re passionate about your work, it makes the people around you want to be involved too.”
— Mike quoting Wanda ([33:46])
“Sometimes if a bit’s not working, it’s like you have a thing in your head and they just don’t…try a different word, try a different physicality.”
— Mike ([36:13])
“I would crush being white.”
— Wanda suggests a new bit she’s considering ([42:09])
The episode is candid, friendly, and insightful, full of laughter and shared respect. Both comedians are open about vulnerability and craft, supporting each other in discussing uncomfortable topics (bombing, coming out, political polarization), and always steering back to the joy and necessity of personal and artistic growth.
Featured nonprofit:
Wanda Sykes’s special:
Movie:
This summary aims to capture all the episode's major insights, memorable lines, and the flow of the conversation, with timestamps for context and easy reference.