Wanda Sykes, the guest on this episode of The Hollywood Reporter’s Awards Chatter podcast, is a trailblazing stand-up comedian, actress and writer who has to her name 17 Emmy nominations and one win; was picked by Entertainment Weekly as one of the 25 funniest people in America and Comedy Central as one the 100 greatest stand-ups of all-time; and is now, for her seventh hourlong stand-up special, Netflix’s Wanda Sykes: Legacy, back in Emmys contention.
Over the course of a conversation at the L.A. offices of The Hollywood Reporter, the 62-year-old opened up about what prompted her, at the age of 27, to leave a steady job with benefits at the National Security Agency to pursue a career as a stand-up; how her comedy changed after she divorced her husband in 1998 en route to coming out as a lesbian in 2008; and some of the hot-button comedy issues of recent years, many of which she has had a front-row seat to: the firing of Roseanne Barr during the making of the reboot of the TV series Roseanne, which she was a part of; the slapping of her friend and mentor Chris Rock by Will Smith at the 2022 Oscars ceremony that she co-hosted; and the targeting by President Trump of comedians including Jimmy Kimmel, on whose late-night show she was set to appear as a guest the night Kimmel got pulled off the air in 2025.
You can listen to the full conversation via the audio player above or read excerpts of it — lightly edited for clarity and/or brevity — below.
On chaperoning a teenage Dave Chappelle on the D.C. comedy circuit in the late ’80s/early ’90s…
“Dave, when his mother couldn’t make it out to the club, he would ask me, he’d say, ‘Hey, can you just sign for me and just say you’re my aunt?’ And I’m alike, ‘All right.’ He was too young to be in the club without an adult, so I would give him rides. And he would mess with my radio, and that’s when I was like, ‘Look. Okay, wait a minute now. You’re taking it too far.’”
On the significance of 2009’s Wanda Sykes: I’ma Be Me, her first stand-up special after coming out as gay…
“The handcuffs were off. It was the first time doing an hour when I could really just say whatever I want to say and just be open.”
On Trump going after late night comedians…
“This isn’t cancel culture. This is fascism. You get canceled when people don’t want to hear from you anymore —you can’t get booked or people don’t want to buy tickets, that’s being canceled. This is the government trying to shut us down and trying to end freedom of speech. That’s two different things.”
On hosting the Oscars in 2022, the night Smith slapped her friend and mentor Rock, and she tried to get Diddy to say something about it…
“We had just finished our bit — we’d had a bit in the audience — so we were going backstage, and I went back to my trailer and was going to get changed, and I’m like, ‘Oh, shoot, it’s Chris [presenting next],’ so I said, ‘I want to be able to hear the audience.’ So I run back to the back of the stage, and I walk in, I look at the monitor, and I see Will on stage, and I’m like, ‘Did he just slap him?’ It’s quiet and we’re all just like, ‘This must be a bit.’ And then when Will got back to his seat and was screaming and everything, Chris was trying to keep his composure and he was like, ‘Wow, OK now’… I’m looking at the stage manager and I’m like, ‘Do I need to go out? Can I go out? Should I go out?’ And he was like, ‘No, just wait. We’re talking to the booth. Wait.’ Sean Combs was the next person to go up — Chris presented to Questlove, and then the next presenter was Sean — so I’m there like, ‘Sean, you got to say something about this, man. You got to say something about this. This isn’t right. This isn’t right.’ And he goes, ‘I got you, Wanda.” And then he’s like [from the stage], ‘Hey, we’ll work this out at the Beyonce party.’ I’m like, ‘Well, that’s not what I was thinking.’ But I was really upset and just disgusted that this industry just let somebody sit out there and then win… [If Smith had been ejected from the theater and then awarded the best actor Oscar,] I was going to do the, ‘Unfortunately, Will couldn’t be here tonight.’”
On wanting to host Saturday Night Live, which she has never been asked to do…
“Something hit me the other day. I said, ‘You know what? I think I would like to do that: let’s host SNL.’ I like sketch, and it’s still a big show, and, especially with the way late night is going down, that’s just an incredible platform.”
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