It’s been more than three decades since Wanda Sykes first stepped onto the stand-up stage—and sometimes it feels like she’s just now getting her due.
The legendary comedian just received her first-ever Grammy nomination for her Netflix special I’m an Entertainer, which also landed nods at the Emmys and Golden Globes. The hard-hitting hour takes on many of the most divisive topics of the year without pandering to either side or ever punching down. “It’s just noise. And I like to try to cut through that,” she says of the way her comedy reacts to the broader political conversation.
In this episode of The Last Laugh podcast, Sykes takes on everything from Dave Chappelle’s anti-trans jokes to why she was shocked Will Smith didn’t get dragged out of the Oscars for slapping her friend Chris Rock. She also discusses hitting the road for her Please & Thank You tour during an election year, how she thinks about her place in the comedy pantheon, and a lot more.
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Sykes and I are speaking the morning after Rep. Lauren Boebert (R-CO) snapped a selfie with Chappelle and another colleague and posted it on social media with the caption, “Just three people who understand that there’s only two genders.”
“Wow,” Sykes says, shaking her head in response. “I mean, if I go to Capitol Hill, I don’t think I’m going to seek her out. You know, like, ‘Where’s Lauren?’ Oh man!”
Whether it was wholly intentional or not, Sykes’ material about the conservative backlash to transgender identity serves as a counterweight to the openly hostile rhetoric that can also be found on Netflix from comics like Chappelle. Instead of demonizing trans people, she chose to make the politicians who are scared of trans women using the ladies’ room the prime target of her jokes.
“I’m not trans, so I’m not trying to go deep into the psyche of a trans person,” Sykes tells me. “But I do know they have a right to exist and shouldn’t be singled out when they’re just trying to live their lives and not be bothered.”
Earlier this year, Sykes told an interviewer that she “totally would say something” to Chappelle about the issue the next time their paths crossed. Months later, she says she still hasn’t had the chance to share her views with him directly.
“Here’s the thing, I love Dave,” she says. “I’ve known Dave since back in the D.C. days. We started together. So yeah, I would love it, I just haven't had the opportunity.”
Of course, they are nominated in the same category (Best Comedy Album) at the Grammy Awards, which will be handed out in Los Angeles in February. Perhaps that could be the moment?
Letting out an extended laugh, Sykes says sarcastically, “Yeah, I think that would be the perfect place to bring it up.”
Below is an edited excerpt from our conversation. You can listen to the whole thing by following The Last Laugh on Apple Podcasts, Spotify, Google, or wherever you get your podcasts, and be the first to hear new episodes when they are released every Wednesday.
You’ve been pretty critical of comedians who complain that they’re not allowed to say anything anymore. What do you think is at the core of those complaints? These are people, like Dave and others, that you’re friends with. Why do you think that they feel the need to complain about that? Because you obviously don’t feel the same way.
Yeah, this is America. You have the right to say whatever you want to say. So I just think it’s false when they say that they can’t. No, you can. But there’s going to be some people who might not like what you say. If you really believe in what you say and what you want to say, then go for it, but just be prepared to deal with the outcome. So to me, it bothers me when comedians say that because now, when you’re on stage, I’m sitting there as an audience member going, but what do you really think?
There is a strange thing where comedians who get in trouble or receive backlash for things that they say come back with, “Well, I don’t really feel that way, but I’m just saying it on stage.” But there is this perception for most audience members that when you see a comedian say something on stage, it’s because they mean it.
Unless you’re doing a character, but then we have to all know you’re doing this character.
Yeah, but the excuse of “It’s just a joke, don’t take me so seriously” doesn’t seem to fly as much now, given that comedians are talking about these big issues and giving their opinions. How do you think about that for yourself? When you are on stage, do you feel like you have to stand behind what you’re saying, even if it’s a joke?
Yeah, I would say what I say on stage is pretty much how I feel. Except maybe with parenting. I exaggerate in that area. Like, I’m not hitting my kids. But I’ve said it before, like, “I can’t hit them, they’re white. My Black ass can’t be beating white kids!”
Another comedian in the same Grammy category is Chris Rock, who responded to “the slap” at the very end of his live Netflix special Selective Outrage. You were obviously there, co-hosting the Oscars that night [with Amy Schumer and Regina Hall], so what did you think of his response all those months later?
You know, I was happy for that guy. And I love that he did it live, because it's like, there’s no taking it back! And I’m pretty sure it was very cathartic for him to get all of that out.
With the Oscars, since you were there as a co-host, were there discussions at that moment about, should we go out and say something and address it in some way?
Regina and I had just finished a bit in the audience and we introduced Chris. So I was trying to run to my trailer, but then [when I realized something was happening], I was like, I want to be in the room, I want to hear this. When I got to the stage, it just happened. And I was like, “Did he really hit him?”
For all of us watching at home, there was a moment where it seemed like maybe it was staged or something. But as the host, you must have known if it was a bit, right?
Not really, because during the rehearsal we just did our part. We didn’t watch the whole show. So I didn’t know what was happening, if it was real or not. And then when Chris said, “He just smacked the shit out of me,” I’m like, “Oh, damn, that’s real.” And I’m looking around like, “Where’s security, what’s happening?”
Did you expect Will Smith to be dragged out by security?
Man, are you kidding? It’s the Oscars! I don’t care who you are, I thought there were going to be some big dudes in suits and they would take him, walk him out, and LAPD was going to be waiting for him on the other side.
Why do you think that didn’t happen?
It’s Hollywood! It’s just craziness, I don’t know. But I do know that Chris didn’t want to press charges, so I guess it started there. Also, we were going to change into pajamas to say good night, but I stayed in my clothes because I was waiting for the producer Will Packer to say, “Hey, I need y’all to go back out.”
But that didn’t happen.
Yeah, it was just crazy. It really messed me up, too.
Yeah, it seemed like it messed a lot of people up. It was traumatic for people watching, maybe just because we rarely see something that real happen in that kind of setting.
Yeah, absolutely. And I know I got some crap because I went on Ellen and said I was traumatized, but I literally was, man. It’s like, I was at my job. I was at my job and somebody smacked the shit out of my co-worker. If this was a Waffle House…
The cops were getting called.
Exactly!
Well, you and Chris obviously go way back. One of your earliest writing gigs was on The Chris Rock Show, and you got to return to the late-night TV world earlier this year when you guest-hosted The Daily Show, which I thought you were fantastic at. And it gave you a chance to react to the news in real time in a way that you can’t always do in a stand-up special. Did you enjoy having a platform like that for the first time in a long time?
Actually, I did. I really did. It was a lot of fun. It’s a lot of work, too, but I enjoyed it. And it’s so cool to be able to talk about something in the moment.
Have you had any discussions with them about making it a permanent gig? There’s just been so much speculation about who is gonna get the job eventually. Is that even something that you would want if it was offered?
I have not had conversations about that. And you know, I’d say no, I don’t think I would want to do that. But I say that right now. Who knows, down the road, especially with kids, it might be nice to stay put in one place and have a schedule and a routine. But then it feels like a job. I’m doing comedy because I don’t want a job.
Well, you had your own talk show for a bit—
And I know how hard it is! And I was foolish enough to do a talk show while I was still doing The New Adventures of Old Christine. I was a series regular. That was the dumbest thing I’ve ever done.
Who would you want to see in that role on The Daily Show? Is there someone who you’re pulling for?
Everyone brings their different take to it. I know Leslie [Jones] really wants it. Ronny [Chieng] is good. I thought Sarah [Silverman] did a great job. Who knows? But you know, I was sad to see what happened with Roy Wood Jr.
Yeah, I thought he was all lined up to get it.
I thought so too. When I guest-hosted and he came on, I was like, shouldn’t we switch seats?
I hope it’s OK to say that you’re turning 60 next year.
Yes!
Do those big milestone birthdays make you think at all about your legacy in the comedy world?
Wow, well, now that you brought it up... damn, thanks for putting that out there. I’m just very, very grateful. And you know, it’s funny because when I started doing stand-up, my aspiration was, I want to be able to travel around the country and play theaters and sell them out. And with this tour, tickets are on sale, and we’re adding shows, the numbers are looking great, I’m selling out places. And it hit me the other day like, oh, wow, I finally hit what I said I wanted to do when I started out. So that feels great. I teared up a little bit. Because when you first start out, you’ve got to get to the city days ahead, do all the radio and press and all that stuff to try to sell tickets. And now I guess my work speaks for itself. Or people are just going to show up. And I don’t take that for granted. It’s taken over 30 years to get to that place where I’m doing what I said I wanted to do.
Listen to the episode now and follow The Last Laugh on Apple Podcasts, Spotify, Google, or wherever you get your podcasts to be the first to hear new episodes when they are released every Wednesday.
