Wanda Sykes is the guest of this episode of Hollywood Reporter‘s Awards talks Podcast, she is a groundbreaking comedian, actress, and writer with 17 Emmy nominations and one win; Chosen by Entertainment Weekly As one of the 25 Funniest People in America and as one of Comedy Central’s 100 Greatest Stand-Ups of All Time; Now she’s premiering her seventh hour-long stand-up special on Netflix Wanda Sykes: Legacyonce again in Emmys contention.
Over the course of a conversation in the Los Angeles offices Hollywood Reporterthe 62-year-old spoke about what led her, at age 27, to leave a steady job with benefits at the National Security Agency to pursue a career as an improvisational actress; how her comedy changed after she divorced her husband in 1998 on the way to revealing that she was gay in 2008; And some of the hottest comedic issues in recent years, many of which have had a front-row seat: Roseanne Barr’s firing during the set-up of a reboot of the TV series RoseanneOf which it was part; her friend and mentor Chris Rock being slapped by Will Smith at the 2022 Oscars, which she co-hosted; And President Trump’s targeting of comedians including Jimmy Kimmel, who was scheduled to appear on his late-night show as a guest the night Kimmel was pulled from the air in 2025.
You can listen to the full conversation via the audio player above or read excerpts — lightly edited for clarity and/or brevity — below.
About accompanying teenage Dave Chappelle on the DC comedy circuit in the late 1980s and early 1990s…
“Dave, when his mom couldn’t go to the club, he’d ask me and say, ‘Hey, can you just sign for me and say you’re my aunt?’ And I’m both, ‘Okay.’ He was too young to be at the club without an adult, so I was giving him a ride. And he was messing with my radio, and that’s when I said, ‘Look.’ Well, wait a minute now. You’re taking it too far.
On the importance of 2009 Wanda Sykes: I’m being meHer first stand-up special after announcing that she was gay…
“The handcuffs were off. It was the first time I had an hour where I could say what I wanted to say and just be open.”
On Trump’s pursuit of late-night comedians…
“This is not cancel culture. This is fascism. When people don’t want to listen to you anymore – you can’t be booked or people don’t want to buy tickets, you cancel. This is the government trying to shut us down and trying to end freedom of speech. These are two different things.”
When hosting the Oscars in 2022, the night Smith slapped her friend and mentor Rock, and tried to get Diddy to say something about it…
“We had just finished our part – we had a little bit of an audience – so we were going backstage, and I went back to my trailer and I was about to change my clothes, and I said, ‘Oh, shoot, it’s Chris [presenting next]I said, “I want to be able to hear the audience.” So I ran back to the back of the stage, walked in, looked at the screen, saw Will on stage, and was like, “Did he just slap him?” He’s quiet and we’re all like, “This has to be a little off.” And then when Will got back to his seat and he was screaming and everything, Chris was trying to keep his composure and he was like, “Great, okay now”… I was looking at the stage manager and I was like, “Do I need to get out?” Can I go out? Should I go out? And he was like: No, just wait. We talk to the booth. I am waiting.’ Sean Combs was the next guy up – he introduced Chris to Questlove, and then the next presenter was Sean – so I’m up there saying, ‘Sean, you’ve got to say something about this, man.’ You have to say something about this. This is not true. This is not true. “I got you, Wanda,” he says. And then it’s like [from the stage]“Hey, we’ll work this out at Beyoncé’s concert.” “Well, that’s not what I was thinking,” I said. But I was really upset and disgusted that this industry would allow someone to sit there and then win… [If Smith had been ejected from the theater and then awarded the best actor Oscar,] I was going to say, “Unfortunately, Will won’t be able to be here tonight.”
Willingness to host Saturday Night LiveWhich she was never asked to do…
“Something struck me that day. I said, ‘You know what?’ I think I’d like to do this: Let’s host SNL.’ I love drawing, and it’s still a great show, and especially with the way late night is going, it’s just an amazing platform.
