Backstage With Gentry Thomas

Whitney Cummings: From Postpartum to Power Moves — Roseanne, Big Baby Tour & Bold Jokes

19 min
Feb 24, 20262 months ago
Listen to Episode
Summary

Whitney Cummings discusses her Big Baby Tour, postpartum experience, and evolution as a comedian who has become more fearless and reckless on stage. She reflects on her work as a writer/producer on the Roseanne reboot, her approach to staying sharp by performing in clubs, and how motherhood has paradoxically made her more dangerous as a performer.

Insights
  • Motherhood and near-death childbirth experiences can paradoxically increase comedic fearlessness rather than soften performers, removing the ability to pretend or play it safe
  • Successful comedians maintain relevance by staying embedded in club culture and performing for non-fan audiences, creating healthy competitive pressure to evolve material
  • Working with controversial figures creatively doesn't require moral alignment; separating artistic collaboration from personal politics is essential for creative growth
  • Touring rituals and town observation (airports, malls, local venues) provide material research and authentic connection to audience demographics
  • Female comedians challenge industry assumptions about who can be edgy, provocative, and commercially successful in mainstream entertainment
Trends
Comedians leveraging personal life transitions (parenthood, health crises) as authenticity drivers for material and audience connectionReturn of prestige sitcom reboots addressing contemporary political divisions through family dynamics and character conflictFemale comedians dominating touring circuit with sold-out shows and building independent brands beyond traditional network televisionPodcast platforms (Good For You) becoming primary distribution channels for comedians to build direct audience relationshipsMoral relativism in entertainment discourse: audiences increasingly separating artist personal views from creative output quality
Topics
Postpartum depression and motherhood in comedyStand-up comedy touring and material developmentFemale comedians in mainstream entertainmentRoseanne sitcom reboot and political representationComedy club culture and performer developmentSocial media impact on comedy and audience perceptionEpstein files and unexpected cultural referencesMall culture and retail brand historyPodcast production and distributionPolitical polarization in family narrativesMoral relativism in artist collaborationsAudience demographics and touring strategyComedy roasts and competitive performancePersonal branding for comediansEntertainment industry gatekeeping
Companies
Victoria's Secret
Mentioned as part of Les Wexner's retail empire connected to Epstein controversy and mall culture nostalgia
Bath & Body Works
Referenced as Wexner-owned mall retailer representing formative consumer experiences of Whitney's generation
Abercrombie & Fitch
Discussed as controversial mall brand from Whitney's youth, part of Wexner's retail portfolio
Limited Brands
Mentioned as Les Wexner-owned company in context of mall retail empire and Epstein connection
HBO
Network that aired Whitney's special containing the squirting bit referenced in Epstein files
Facebook
Used as example of platform with problematic founder now facing legal consequences, in morality discussion
Spencer's
Referenced as novelty mall store from childhood where Whitney first encountered adult products
People
Whitney Cummings
Guest discussing her Big Baby Tour, postpartum experience, and Roseanne reboot work
Gentry Thomas
Host of Backstage With Gentry Thomas conducting interview with Whitney Cummings
Ron White
Mentioned as fellow comedian who commented on Whitney's pregnancy softening her stage presence
Tony Hinchcliffe
Referenced as comedian who noticed Whitney's softer demeanor during pregnancy
Dave Chappelle
Included in Whitney's dream comedy lineup as headliner known for handling drunk audiences
Bill Burr
Named as essential inclusion in Whitney's ideal comedy club lineup
Bobby Lee
Mentioned as comedian Whitney would include in her dream comedy club booking
Rachel Feinstein
Praised by Whitney as brilliant New York-based comedian married to a firefighter
Steph Tollev
Described by Whitney as ridiculously funny comedian for her ideal lineup
Nick Swartzson
Named as comedian who must be included in Whitney's dream comedy club booking
Mark Marin
Selected by Whitney as MC for her dream comedy night for his witty introductions
Roseanne Barr
Creator of Roseanne show; Whitney worked as writer/producer on reboot addressing political divisions
Laurie Metcalfe
Starred in Roseanne reboot alongside Roseanne Barr; Whitney wanted to learn from her work
John Goodman
Cast member in Roseanne reboot that Whitney worked on as writer/producer
Jeremy Piven
Referenced in anecdote about Mark Marin's witty commentary at Comedy Store
Les Wexner
Epstein partner and founder of Victoria's Secret, Bath & Body Works, Abercrombie & Fitch
Quotes
"I plan to use postpartum depression as an excuse for the rest of my days. Whenever I'm on brain and postpartum depression, anytime, it's so exciting."
Whitney Cummings
"I almost died in childbirth. You think I care if you're triggered? There's a new level of not caring that I think I'm excited to be at."
Whitney Cummings
"Comics keep comics funny. You have to stay in the clubs. You have to stay performing for fans that aren't necessarily your fans."
Whitney Cummings
"I'm not God. And I'm not the judge jury and the executioner. Working with someone or supporting someone creatively means you agree with everything they've ever said."
Whitney Cummings
"As soon as the files dropped, I was like, but is this real? Is this real? That's AI. Is that AI?"
Whitney Cummings
Full Transcript
What's up, dude? Hey, what's up? Our next guest is fearless. She's witty, she's intelligent, she walked on stage pregnant, and she walked off stage stronger. And now, she's on the road. With the big baby tour, and she's proving that growing up doesn't mean quieting down. Let's welcome to the show the brilliant, the beautiful, the hysterical, Whitney Cummings. Hey, Whitney, how are you? Good morning. Are we together? I believe so. We've just connected. I helped. I'm flustered at that intro. Thank you. I felt like I was an MC at an old smoky comedy club, you know, bringing you up on stage. Ladies and gentlemen, here she is. Come on up. First of all, she had a terrible childhood, so keep clapping. Yeah, she's been torn, so she's going to be funny. First of all, congratulations on the tour, this big baby tour, also the baby, and getting through the postpartum from what I've read, you're past that, or is it still sticking around? I plan to use postpartum depression as an excuse for the rest of my days. Whenever I'm on brain and postpartum depression, anytime, it's so exciting. Every time I'm like, I can't find my keys. I have mom brain. Everyone's like, you've never been able to find your keys. Stop blaming your child on this. I'm like, it's mom brain. It's mom brain. It's postpartum depression. It's like, no, you've always just cried uncontrollably in the parking lot of Carl's Jr. That's your thing. Do you think this mom thing has made you a little softer? Has it made you a little more dangerous on stage? What do you think? How has it affected you? Great question. It's funny because when I was pregnant, all a bunch of comics, like Ron White, it's fine to name check him. They were all like, even Tony Hinchcliffe was like, what is going on with you? I was like, stop it. They were getting flirty with me, and they were like, it's not like we're into pregnancy. This is your softer. I was like, yeah, I guess it does soften you a little bit. Look, was it having the kid? Was it reading YouTube comments? Who knows what broke me? I think that I came out swinging so hard to people with doing the roasts as the thing that I think people knew me from initially. I think I've maybe always been softer, but people maybe haven't seen it because you only see me in sparring fight mode. But I think it definitely has made me more dangerous. Frankly, I think the word should just be reckless because you lose the ability to pretend or be fake, at least I did. The idea of playing it safe is like what? I almost died in childbirth. You think I care if you're triggered? There's a new level of not caring that I think I'm excited to be at. Sometimes it backfires on Twitter, but I'd rather make a mistake every now and then and go right up to the line and maybe just cross it. That's our job as comics. It's not to be universally beloved by everyone and to never miss. If you want to see this reckless, glowing, new, softer side of Whitney, make sure you go to whitneycomings.com. She's currently on the road on this big baby tour and she's got fans from all walks of life. Some you expect, some you absolutely don't. When you found out that one of your boldest bits was being quoted in federal documents, did you think, well, that's a new demo? I mean, your squirting bit made the Epstein files. That's amazing. Did you hear about this? I'm assuming it's true. I think that they were brilliant in the timing of when they dropped the Epstein files because it's like, why are they waiting? What's the wait? What's the holdup? What's the holdup? I was like, oh, they were going to wait till we all had broken our brains to the point of thinking everything might be fake with AI. As soon as the files dropped, I was like, but is this real? Is this real? Is that true? If this had happened even two years ago, you wouldn't be like, that's AI. Is that AI? So they, I don't know how coordinated that was, but yeah, I guess apparently he forwarded the link of clips from my HBO special, I want to say. What I read was that he was communicating about wanting to see you because he really loved your squirting bit. So you must have turned him on at some point with that squirting bit. I made it. Well, female comics don't turn men on. We know that didn't happen. That was like, he's like, I'm going to go see a make-a-wish kid. Like what he, yeah, I don't think. At least you're cleared. By the way, we want to clear Whitney's good name. She had no relations with Epstein. He just, one of her bits, you know, made him laugh. That's all. No, I think he came to a show in maybe Palm Beach or was trying to get tickets or something. I think he tried to get tickets. I don't know if he actually showed up or not. I was about 30 years too old for him. Yes. 31. Yeah. Yeah. You needed to be in your teens if you wanted to hang out on that island. When I was a touring DJ, Whitney, I had this little ritual where I would go to the local mall. That was my thing where you could really tell a lot about a town if you just like walk through the mall. And I would, it was a lonely life, you know, because you're all alone during the day, similar to a comic. So I'm wondering, do you have a ritual when you go from city to city, something that you like to do to catch the vibe in the town? It's a perfect question and genius segue because I posted this video on TikTok the other day about so Epstein, since you brought up, he was partners with this guy, Les Wexner, who is viral right now for his testimony, but he owned Victoria's Secret, Bath & Body Works, Limited and Abercrombie, the mall. Yeah, that is the mall. The mall. So what you were doing, I was also doing, and it was like, that was mall culture. And now we're seeing like, hold on, all of the stores that I was in as a teenager, every pair of underwear I bought, every perfume I bought, every, I remember going into Abercrombie and Fitch and being like, these aren't shorts. This is denim underwear. There's no one can, what is this? Like this is not, this is like Oshkosh Bagosh denim, you know, and you look back and you're like, all those days of being at the mall or like just ruined. The first time I saw a dildo was at Spencer's. I mean, come on. These kids. I'm actually so true. You would go to Spencer's as a kid and you're like, I would get those glasses with the mustache and you're like, is that a coppering? Like it was all just like pasta that was the shape of dick and balls. You're like, what is this store? But yeah, I will do, I walk around the mall. I will try to go to, like, I'm kind of a dork tourist. Like I'll go to the, you know, the local museum or the local store so that I can either make fun of it or talk about it or whatever on stage that night. But nothing really gives you a more sort of comprehensive taste of the town than the airport. I think once I land, I won't just go straight in the car. I mean, let me just like hang out here for a little bit and see what I'm dealing with. That usually tells me everything I need to know based on the line in Cinnabon. If you own your own comedy club, Whitney, and you were booking the ultimate comedy night, your dream lineup. Who is the MC? Who's the opener? Who's the feature? And then who's the headliner? And possibly there's like a, there's a guest. Maybe there's a guest host or something like that that's in the crowd that just has to get up. Do I like the audience? Do I like the crowd? Yeah, it's your club. So hopefully you like them. Um, okay. So, woo. MC, start with who's MCing the night? These are people that wouldn't normally MC because they're headliners, but I'm going to cast it funny. Mark Marin, uh, will have to MC. He's not an MC, but he is so funny at pretending he likes a comic he's about to introduce or what he says after a comic brings him on. He can't help himself. So there would be nothing funnier to me. Like one time he was, he, he went on stage at the comedy store after Jeremy Piven because Jeremy Piven's like doing standup and he goes, keep it going for the actor. He forgot his name. No, just like the actor. Uh, like he just can't help himself. And so I just, I think everyone would really enjoy his intros for people and his commentary after. Um, let's see. Give it tell. I think I would put up maybe later, maybe at the end, like he's a headliner later. He's the headliner for sure. But the later Dave goes on sometimes just like the better and he'll sometimes make fun of the comics before. So he should have to sit through everyone. Um, but yeah, he would definitely go the latest. He's so good with like drunk people, just asleep in the audience and stuff. Uh, Bill Burr would have to be in there. Um, Bobby Lee would have to be in there, uh, somewhere. Um, Rachel Feinstein, uh, lives in New York. She's brilliant. Her husband's a firefighter. Um, she just like, she kills me. Um, my gosh. It'd be a hell of a lineup right there. That's a full night. Steph Tollev. Steph Tollev is ridiculous. Uh, she's so funny. Robbie Hoffman. Um, I'm trying to like, you don't want to forget anyone, but that's enough. That's a hell of a lineup. Different types of people. That would be, that would be a sold out show to drink minimum. What a hell of a show. I'm missing so many people, but Dick Swartzson, Nick Swartzson has to be in there somewhere too. I want to go to this comedy club. You should open up your own club one of these days because I think you'd be a great booker. Yeah. Why did you just give me a demotion? You know what you should do? You should work at a comedy store. Um, yeah. I, well, I think that I'm, you know, I think the funniest comics and I'm love comedy, you know, there's a lot of comics who like get successful and they get everything and then they stop being funny and you're like, how come they're, what happened? They're not hanging out with comics. Like comics, keep comics funny. And, you know, like getting in the green room and having people like come at you and spar at you and, you know, uh, going to see comedy and see what other people are doing and just going like, Oh, I gotta like step it up. Or like, Oh, like there's a healthy competition that we have. That's like, Oh, like this person killed. Like I have to go after them. I have to kill him and harder. You know, I think that like you got to stay in the clubs. You got to stay performing for fans that aren't necessarily your fans that came to see someone else and you're in between them and the person they came to see. Like those are the people you have to win over. Like that's what keeps comics funny. Um, so I just happened to like be in the clubs a lot because I don't want to become like jaded and, you know, like out of touch and just like, you know, like where are you from for 45 minutes? Well, I want to see you kill the coming up this season. The big baby tour is going across the country right now and you can find out more by following her on social media or listening to her podcast, which is called good for you. I think you got lots of episodes up there. So plenty of binge listening. You could do one comedian. I want to ask you about loves it. Oh, I'm sure he loves loves when you can have you ever squirted on the show. He's listening to it from hell or wherever he is, wherever he is. Yeah. There's one comedian I would like to ask you about because I read that you were a producer or a writer on the show, the return of Roseanne. How did that get? I'm going to start taking a drink as you asked me to buy time. Yeah, go ahead. Buy some time. You were going to write for the reboot of the Roseanne show. How was that interaction? How did that go? Roseanne is brilliant. And I grew up idolizing Roseanne and the show is why I wanted to get into sitcoms. The show was the first place I saw what my house looked like. You know, no shade. It was like the Cosby show rest in peace, but like they were rich and there were doctors and they had their fans. Like I didn't relate to what I thought it was funny. You know, sitcoms were always like everyone was just rich. You know, there was no talk about money or anything in Roseanne. Like they were fighting. They were kind of roasting each other. I'm like, that's what my family, that's how we talk to each other. That's what my couch looks like. This is, you know, that's what my kitchen looks like. That's what we've, you know, we can't pay the grocery bill. Like, so I can't overstate how important that show was to everyone. But I can speak for myself and that it changed my life. And, you know, having the opportunity to work on it was a no brainer. It was at the time where the beginning of families being torn apart by how they voted and she, I believe at the time had openly voted for Trump. And I was like, what better thing to talk about right now than showing families like where they voted differently in Jackie, her sister in the show, the great Lori Metcalfe, who I've always wanted to work with or even truly just watch work as a fan. I wanted to learn from her and John Goodman. And I was like, if we can have Roseanne in the show, vote for Trump and Jackie, vote for someone else and watch what's happening in a lot of these, like in real time, like I can't think of a more relevant thing to be a part of right now. And so it was a no brainer. People were mad at me, like they, like, as if I dragged her to the voting booth and made her vote for her. Like it was kind of very upsetting to a lot of people that this happened. But I think that's what it was about. It was that was the idea is to go head on at this. And she's brilliant. And in terms of her private life and, you know, her tweets and the way that she chooses to engage with her audience is like her business, you know? And, you know, I think that comics like are often, you know, there are people that say what they think, like, like it or hate it, you know, agree with it or not. If what you're doing is true to you, you know, it is what it is. And I think everyone deserves to exist and everybody deserves to have their opinion and everyone deserves to be pissed off if they're pissed off. And to me, when someone, I get very soon as someone gets called crazy, I get interested in what they're saying. Because I'm like, is this person crazy or do they just know something before everyone else knows it? So I'm not scared of that. I grew up with a crazy woman that raised me. I sort of like I aspire to be a crazy woman. And maybe I already am one, but I would rather, you know, that's a space that I like to be in. It's dangerous. I don't necessarily, you know, even when we were making the show, I didn't agree with everything, you know, Roseanne said or did, but it's I'm not God. And I'm not the judge jury and the executioner, you know, and it's interesting because when people want to take like a moral stance, like I can't believe you worked with Roseanne, I'm like, you're posting this comment from a platform that is we're going to look back in 20 years and be like, remember when we were all on Facebook and now this person that started it's in jail. I mean, everything has how deep do you want to go in this morality thing? You're posting this from a phone that the cobalt in it was mined in the Congo by children like how far do you want to go on this, you know, in terms of morality police, you know, but I have thick skin. I don't think that working with someone or supporting someone creatively means you agree with everything they've ever said. And I'm I'm I'm attracted to people that kick up stuff. We're all we're all imperfect at the end of the day, Whitney. I could sit here and talk to you all day, but I know you got a baby to take care of. And you've got and you've got to get ready for this big tour that you're out on. She's built sitcoms. She's built specials. She's on tour. And then now she's built this perfect big baby, the big baby tour. It's out there right now. And if you want to see it, you can see her turn real life into a master class. Go get a ticket by going to Whitney Cummings dot com, coming to a city near you. Thanks so much for your time, Whitney, and keep it rocking out there. Nice. I think you've it's fine if you've got I've done this for a long time. You are excellent at what you do. Oh, thank you, Whitney. I appreciate that. Truly like a pleasure. Well, I hope I hope we could do it again. That would be great. You are a pleasure. All right, Whitney, peace out. I could talk to you all day, but we'll catch up later. I know you got to go. Thank you, sir. Thank you. Thank you. See you.