When Wanda Sykes first toured the school that her now-14-year-old twins attend, not only were she and her wife, Alex, won over by how LGBTQ-inclusive it is, but the comedian imagined how things would have been different if she had grown up with such acceptance. “I could’ve saved myself a lot of unnecessary dick in my life,” she jokes in her latest Netflix stand-up special, Wanda Sykes: I’m an Entertainer, which premiered on the streamer in May. From LGBTQ issues to police violence against Black Americans, Sykes packs a remarkable amount of political humor into the hour of comedy, all with a personal approach that, she says, “makes it more relatable.” The Emmy-winning performer — who also starred this year on two series, The Upshaws and The Other Two, and is planning to go on tour next year for the first time since before the pandemic — speaks with THR about what she still doesn’t find funny, explains why she shot her special in Philadelphia and shares her prediction for the 2024 presidential race.
In your Netflix special, you tackle everything from anti-trans bathroom legislation and laws against teaching critical race theory to white privilege, Jan. 6 and police killings of Black Americans, including Elijah McClain. How do you get an audience to go along with so much political humor for an hour?
I’ve pretty much established an audience who expect me to say something. It is pretty challenging to do that and to make it funny and not so polarizing. And I think what I’ve found from doing that is — instead of talking about politics — it’s more about how it affected me. Just personalize it. It’s not like I’m talking about “This thing is bad.” It’s how I or my family reacted to it, or how we discuss things.
You’ve previously said the one topic you can’t find humor in is the overturning of Roe v. Wade. Is that still the case?
Yeah, it is. The only eggs I have left are in my refrigerator — so it’s not really a concern for me, but it is a big concern. I have a daughter now, so I do think about that. It’s just all so scary.
You filmed I’m an Entertainer in Philadelphia. Is there any reason why you chose to shoot in that city over any other?
There are some cities that are just really good as far as the audience, and I have a nice following. Washington, D.C., is a home run for me. That’s where I started doing stand-up. But this special, I really wanted it to be in Philadelphia, especially with what I’m discussing [and it being in] such a battleground state — and also just to thank Pennsylvania [voters] for the 2020 election, for coming through [for Joe Biden].
You and your producing partner Page Hurwitz signed a first-look deal with Warner Bros. TV earlier this year. Have you been back to work on developing things since the writers strike ended?
The writers strike was rough, but I’m so glad we got it done. It was crucial. Now our production company [Push It Productions] — we’re back developing and taking meetings with writers and coming up with shows to pitch.
How do you feel about touring next year?
I’m so excited about it. This is the first time that I’m doing a real tour. Because I’ve been fortunate where I was working on other projects, and if it wasn’t The New Adventures of Old Christine or my own show or whatever, I had things going on, so I couldn’t do a legitimate tour. I would take dates here and there. The kids are older now, so I feel OK about hitting the road. Maybe some weekend they’ll come join me.
How is it different to shoot a special as opposed to doing a regular stand-up show?
When you’re filming it, you’re definitely in your head a little bit. I shoot two shows, so the first one is like, “OK, let me get something in the can. Let me just make sure we got it structurally and technically.” And then the second show, I just [let] loose, have fun, actually improv some stuff sometimes, [and] I stumble on stuff. Because I already have the safety of knowing I have one. We always end up using the second show.
How much thought did you put into what you wear in the special?
We were in Paris for Christmas. My wife is French, and we were there for the holidays. And I knew we were going to shoot the special in February, so I was like, “Man, got to figure out what I want to wear.” And I knew I wanted something different. I didn’t want to go with a suit. I wanted to be a little bit more casual and have a little bit more fun because I’m rolling around on the ground. I’m much more physical in this one. And we’re just shopping in Hermès and I saw this jacket. It’s red, white and blue. It’s denim. And I was like, “That’s it. I think this is what I’m going to do in Philadelphia.”
Some of the funniest physical comedy — improbably — in your special is when you talk about how you are approaching a possible second breast reconstruction, possibly via fat transfer, after having a double mastectomy more than a decade ago. Did you decide yet what you want to do?
Now it’s like I have a lot of miles on these breasts, so it’s time to either get new tires or do some rearranging, [which is] a much longer recovery process. I’m still going back and forth about that.
Do you live and breathe politics when you aren’t being a performer?
I don’t know. Right now, because of the kids and all, I have to read what they’re reading, which is annoying. If they have a book report, and I go, “Hey, did you read this book?” And they’re like, “Yeah.” And it just sounds like they’re winging it — so I’m like, “Shit, now I’ve got to read this damn book to make sure they’re on top of what they’re supposed to do.” So, a lot of my free time is [taken up].
After the recent New York Times presidential poll came out that showed Donald Trump beating Joe Biden in five of six swing states, many Democrats started freaking out. Do you have a prediction for whether Biden will win in 2024?
Yes! Come on. We acting like he didn’t do it before. He’s beating him already. He’ll do it again. I’m not going to worry. I’m not going to stress. I’m not going to be anxious for nothing.
This story first appeared in a November standalone issue of The Hollywood Reporter magazine. Click here to subscribe.
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