Chelsea Handler Grows Up (Kinda): Queen of Caustic Comedy Gets Self-Aware
Photographed by ALEXANDRA GAVILLET

Chelsea Handler Grows Up (Kinda): Queen of Caustic Comedy Gets Self-Aware

The comedian opens up about her new stand-up special, white privilege and how her psychiatrist helped her discover empathy: "I had no idea what a c*** I'd been."

It is both entirely appropriate and utterly insignificant that Chelsea Handler is seated before me on this Friday morning in October stoned as could be. In fact, I'd have hardly noticed had the comic, talk show host and author of five best-selling books not brought her current state to my attention. But as she joked in HBO Max's recently released Chelsea Handler: Evolution, her first stand-up special in six years, she's built to withstand considerably more than the morning's joint.

As its title suggests, the new hour, filmed before a socially distanced audience earlier in the pandemic, features little in the way of celebrity gossip, which Handler famously made hay of as the host of E!'s Chelsea Lately for nearly a decade. Instead, Handler, who has largely traded vodka for some combination of weed, meditation and therapy, takes a page from more vulnerable comics like Hannah Gadsby or Neal Brennan. She uses her time onstage to reflect on her often devastating past, including how the tragic death of Handler's brother when she was just 9 shaped the now single 45-year-old.

Lounging in her Bel Air backyard, Handler speaks just as openly ­— and hilariously — about her many former employers (at least one of whom she dated), her recent exploration of white privilege and her complicated relationship with Donald Trump.

You went from performing in front of thousands to a crowd of 20 or 30. How does that impact you?

I had said to my agent, Nick Nuciforo, "Find me clubs [that are open]. I'll go anywhere. I just have to run this set 20 [more times] and I've got it." So, I went to Providence, Rhode Island, and I worked out at the Comedy Connection. It was really humbling to try and tell that story [of her brother's death] in a comedy club with 10 women who are super fans and their fucking husbands that they dragged there pissed. It's blue-collar Rhode Island, and the men fucking hate me there. Sorry if I'm yelling. I yell when I'm stoned.

I can handle it.

So, it's 10 people who like me, and 10 who are like, "Wait, you're telling a story about your brother dying?" Because I was working it out and rearranging things, and I was really bombing. I'd never treated stand-up with such respect before. I was diligent this time ­— I was taking notes, and Brandon [her assistant] and I would go home every night [and go over what worked and what didn't]. Before, I abused my privilege all the time; I would be shit-faced by the second show and go, "How did it go?" Obviously not great. This time it felt like I was so much sharper and more of an adult, and even though there's a part of [me now] that isn't as abrasive, I still have my edge.

Not too long ago, you were saying that you wouldn't do stand-up ever again. What changed?

I just associated that whole period of my life with Chelsea Lately. It was like I was rebelling against my childhood. So, first of all, I had to get my head out of my ass. And once Trump was elected, it really did change my whole life. I was like, "Oh, no, no, no. I'm not going to be one of those people who stands by and doesn't say anything." It was earth-shattering, and it woke me up to how easy things were for me. To come to terms with my entitlement and my privilege is really humbling.

You joke about how you used to just lose it on Trump supporters …

Oh yeah, I got into it with a lot of people. I was a hot mess. I'd go into my last job, my talk show at Netflix, and turn on MSNBC. The writers would have their meeting, and I'd go in for, like, 10 minutes and then just come back out and be the most bitter, angry person. I think people just got sick of hearing me bitch about [politics]. Of course, in retrospect, a lot of people were sick of hearing me bitch because they were fucking entitled and didn't think it was going to get this bad. But it was really taking over my life. I couldn't work. I couldn't sleep. I couldn't eat.

Is there anyone in your world saying, "Chelsea, you're spiraling"?

I think people were really scared of me at that moment, so they weren't telling me, but I picked up on it. Then I found my psychiatrist, Dan, and he said the first thing that made sense, which was that I had no empathy. He opened up my whole world and gave me the gift of self-awareness. I had no idea what a c— I'd been. I thought I was just being honest with everybody. I thought I was doing everybody a favor. Like, "You're so lucky that you know me and that I'll tell you the truth."

So do you go back and …

Make amends? No.

You don't do an apology tour?

Oh, I'll never be that fixed. I remember asking Dan, "Do I have to call and apologize to people?" He was like, "No, but you have to do better now." He challenged me to really take a look around and read a ton of books about not being so self-absorbed.

You recently went on The Ellen DeGeneres Show, which has been rocked by accusations of a toxic culture. Do you ever worry in this environment about people coming out of the woodwork to say things about you or your past shows?

No because there would be too many people with good stories who have worked for me. But I'm sure I was badly behaved. Hello, my whole career was bad behavior.

I'll admit, I was surprised to see you return to NBCU, home to E!, with your 2018 producing deal.

Yeah, going home to roost. Next year I'm going to do a talk show on Netflix. I just circle the drain.

What are the stories you want to tell now and have they changed?

I've never taken producing seriously. I never really had the time. I had the companies and the deals, and we'd do the bare minimum. But now it's an opportunity to dig a little deeper. As far as me personally, I'm eager to turn my book [Life Will Be the Death of Me] into a TV show and star in it.

You've gone through this evolution and you feel like you're a different person now. I'm curious, has Hollywood accepted the new you, or does the industry still want you to be the brash, wild lady it knew?

I'm sure they do. I definitely get that from my manager, Irving Azoff. When I was going off about Donald Trump in the beginning, he was like, "Can you be funny again?" I'll never forget, I was up at the Glen Centre, and one of his friends, who's the guy with the [NFL's] Eagles? [Jeffrey Lurie.] His wife comes up to me, like, "Oh, sweetie, I love how political you've gotten. Irving says, 'Well, she's killing her career.' " I went over to his house for dinner a few nights later, and I go, "Hey, dipshit, can you not tell people around town that I'm killing my career when you're my manager?" (Laughs.)

There is definitely a school of thought that says performers should stay in their lane.

I'd rather be on the right side of history and actually stand for something than be somebody who's more worried about my career. I have enough money to get me through if need be.

You had one of the first streaming talk shows with your 2016 Netflix program. In hindsight, would you have done anything differently?

It definitely wasn't some runaway hit, for sure. But [ending it] was mutual. I was over the idea of running a show and being responsible for 50 people every day, and managing those moves, and being in an edit looking at yourself. I had outgrown the talk show format in terms of me. I wanted to do the documentaries, and I said, "Can I do a documentary instead? We can take a year off [from the talk show] and then regroup." Once we did the doc [Hello, Privilege. It's Me, Chelsea], we both understood we're not doing the show anymore.

That 2019 doc was a deep dive on white privilege, a subject that's gotten considerably more airtime in 2020. What did you learn in that process and how did it prepare you for the larger cultural reckoning that we're experiencing now?

I'd done a group of four [docs] for Netflix called Chelsea Does, and out of the four I did ­— on drugs, marriage, Silicon Valley and racism — I was like, "This is so interesting for a white person to be pushing this conversation. We should do more." But the whole series was my thirst for seriousness. I wanted to remind myself that my brain was still working after eight years of gossiping [on E!]. I was very dehydrated for an intelligent subject. Then that one resonated with people, and certainly with me, so I wanted to do another. They'll pretty much let you do what you want at Netflix. Then no director would sign on.

What would they say?

People would not go near the topic. No one. Black people, white people. And I can't, as a white person, shoot a documentary called Hello, Privilege. It's Me, Chelsea with a white director. That was understandable. But there were also Black people who were like, "You're going to get so much shit for this." Even Netflix said, "We just want to warn you you're going to get a lot of backlash." I was like, "Yeah, welcome to that party."

Backlash isn't exactly new to you.

No one's more equipped for that than I am. But I didn't think I was going to get backlash. I'm like, "We're having a good conversation that nobody has the balls to have. And if I'm hanging myself out to dry, maybe people who look like me and relate to me will start asking themselves some deeper questions." I've definitely gone off on a lot of my friends on this matter — and I don't try to patronize, but I've done my fucking homework and I continue to do it. I just finished an 800-page book about Frederick Douglass, and now I'm reading Caste by Isabel Wilkerson.

So were the folks at Netflix, right?

Maybe I missed it, but I don't think there was a lot of backlash. I don't know what the numbers were, like how well it did, but it was definitely before its time. People weren't interested in the topic. Even getting people to agree to be on camera [was hard].

You're back with a stand-up special, and rather than go to Netflix, the top dog of stand-up specials, you chose HBO Max. Why?

Netflix has a little too many comedy specials, if you ask me. Doesn't make you feel very special.

How have they made you feel special on HBO Max?

Bob Greenblatt bought the special when he was still in charge there. Bob had given me my very first development deal when he worked with David Janollari, and then [years later] he made me act in that sitcom that was so bad, Are You There, Vodka? It's Me, Chelsea for NBC. He just gets me and likes me. You don't need a million fans in this town. You just need a couple. So, with this special, I had to showcase it [with a performance of my set] at the Annenberg. I wasn't going to get the same amount of money I might think I deserved [if I didn't]. All the networks came out, and Bob emailed me that night and said, "I'm going to buy it." And I was like, "Great."

How did it feel to do a showcase at this point in your career?

Humbling. But I was like, "Bring it on. I'm going to prove myself again. I'm not scared of any of you fucking people." I knew I had it.

You performed at Dave Chappelle's comedy camp [aka Dave Chappelle & Friends: An Intimate Socially Distanced Affair] this summer, too. What was that like?

I only went for one night because I can't be in an environment where there's that much fun for more than one night anymore. I'm 45. They're like, "Stay another night." And I'm like, "Oh, I have to be somewhere." But really I was like, "Get the fuck away from me. I can't handle two nights of this. You're partying till like 5 in the morning." But I hadn't been in that scene in so long. I have some comic friends like Sarah Silverman and Amy Schumer, but I'm not in the scene the way I once was. To go back was intimidating.

You weren't there when Louis C.K. was there, were you?

No, no, God, no.

I'm curious, what would you have done if you were?

I don't know. I don't know him at all. … I'm sure there were people who were really happy to see him, especially other comedians.

And still others, and you've talked about this, who feel he needs to address what happened.

Yeah, I think all that's really required of people that are put in a situation where there is guilt is saying, "Whoopsiedoodle. I didn't know that I wasn't allowed to whip my penis out whenever I felt like it. Now I know better, and I'm not going to do that again." I don't know the details of him, but I definitely have heard the stories. And I don't know his apology level, but why not? We don't want to cancel all the talented people.

You recently engaged in a Twitter war with one of your exes, 50 Cent.

Yeah, when he came out as a Republican. (Laughs.) I'd have sex with him again if he voted for Joe Biden. For sure. [Handler and 50 Cent have since connected offline, and she says he'll be voting for Biden.]

Your relationship past is a real who's who of the industry, including the former president of E!, where you had your show for years.

Oh my God, Ted [Harbert]. I remember when I broke up with him, I called Kevin Huvane, who was my agent at the time, and I was like, "Hey, did people think it was weird that I dated Ted Harbert?" He was like, "Chelsea, yes." Talk about lack of awareness, I was like, "Why is everybody talking about it? What's the big deal?"

Then you broke up with him and proceeded to speak publicly about how he'd been "fucking obsessed" with you and how you'd come home to him watching your show on TV.

I'm so terrible. No wonder I'm single. (Laughs.)

Can I ask: How often are you going to therapy now?

Oh, I don't go now.

No?

No, he ended up annoying me, too. (Laughs.)

This story first appeared in the Nov. 2 issue of The Hollywood Reporter magazine. Click here to subscribe.