Chelsea Handler Knows She’s Privileged

Despite the chaos that’s befallen America in the past few years, the events that transpired in November 2016 have given Chelsea Handler a new lease on life. The comedian has, she says, taken a long, hard look at the world, and an even harder look at herself. Taking in her life of decadence, Handler says she realized she’d allowed herself to become complacent in a political laziness that allowed a delusional, unqualified man to take a seat in the White House.

From that epiphany came a newfound dedication to political activism, a tell-all memoir, and a new Netflix documentary, Hello Privilege. It’s Me, Chelsea (out Friday, and produced by Conde Nast Entertainment), that dissects the thorny topic of white privilege and her role in it. Early in the documentary, Handler attends an open mic night at USC themed around this very problem. She hangs around in the back, watching a student pour out his anguish through spoken word, before being invited to speak herself. She hesitantly stands in front of the crowd and announces her desire to have a conversation, but the students argue that a conversation isn’t enough. One says she’s embarrassed to be in the same room as her.

It’s a precursor to the revealing nature of the documentary—rather than evade her past, in all of its colorful and sometimes controversial facets, she frames those experiences around a desire to become a better ally. Hello Privilege, It’s Me, Chelsea displays a new side of Handler. Contrary to the loud and unapologetic comedian that has graced our screens, this new Chelsea Handler is willing—nay, wants to take a step back and listen.

Chelsea Handler is probably the last person you would expect to make a documentary on white privilege, which is why the finished product is so fascinating. On a rare moment of downtime during her ongoing stand-up tour, Handler spoke with GQ about her time of self-discovery, how politics made her a better comedian, and why she’s running out of ex-boyfriends to reunite with.

GQ: What was the decision behind making a documentary on white privilege, and why now?

Chelsea Handler: I think it was just me waking up to the 2016 election and taking a deeper look at myself, and the effects of Donald Trump being elected and why something like that would happen. I was kind of stuck in my own naïveté of, oh, sexism was over, we were going to elect our first female president; racism was over when we elected Barack Obama. Just the idealism and the naïveté that came along with that, and not knowing more and not being more educated. I was thinking about what I was putting out into the world, and actually doing a really deep dive to understand my own privilege, because I, along with tons of white people, assumed that white privilege was just for a certain section of society, and it’s not.

Would you say that the 2016 election was the catalyzing moment where you realized your white privilege, or was it more of an accumulation of factors?

That was the biggest moment in my life that changed me. It made me take a really honest look at myself, and I had been moving so quickly throughout my life that it prevented me from doing so. I thought I worked really hard, I thought I was really talented. I thought those were the reasons for my success. It never occurred to me that being white was a huge benefit to me. I never thought about that because I didn’t grow up with people of color. When I grew up and started looking around and I was, like, “Well, where do I live?” I live in Bel Air, and I think I’m diverse. I grew up in a white neighborhood in New Jersey and then I moved to Santa Monica, and then I moved to Brentwood, and then I moved to Bel Air. What the fuck do I know about diversity when I’m living my life like somebody who’s just white and is used to being around other white people?

One thing that stood out to me in the documentary was when you said, “I wouldn’t have gotten away with my career if I was a black girl.” Was there a moment where you came to that realization?

It wasn’t one specific moment but it was just a lot of eye-opening. It felt really good to look outside of myself and get out of my own experience and start to think about how other people go through this world, and what their hurdles are. And to be sensitive about it, because to be a better advocate and ally, you need to be educated. I just felt like I needed to know more, and I didn’t understand why so many people deny the idea of white privilege, and I think it’s because people with privilege don’t want to lose what they’ve got.

Well, white people see equality as oppression in a way, and I guess that’s a difficult realization to come to. You talk to white people about white privilege but they’re kind of blind to it. Is that frustrating to you?

It was frustrating. But I wrote my recent book, Life Will Be the Death of Me, made the documentary, and a cannabis line. Those were the three things I focused on last year, and they were all coupled together in being more tolerant of people who have different opinions. And that goes for people who are white, and are racist or do racist things. I think we all have inner racism and we all have prejudices that we follow or learn without knowing it. That’s not the problem. The problem is denying it.

I couldn’t help but compare this documentary to your Chelsea Does episode on racism. Did that ever cross your mind while you making Hello Privilege?

Yes, that was the subject matter that I cared about the most. That was the most compelling thing for me. In the first series, racism was the thing I was the most passionate about because I learned a lot, even though you’re only scratching the surface because it is such a huge subject matter. For me, it was important to make it personal because I did the racism one thinking I was woke and I knew it.

I was unapologetic for all the things I have said in the past that have been racist or hurt people’s feelings or affected different marginalized groups. I was at a place where I was like, “No, this is unacceptable. I shouldn’t do this anymore.” All of the people in the creative world have to wrestle with it—and it shouldn’t be a wrestle. There are other funny subject matters. We actually don’t have to go to the lowest common denominator. You don’t have to do that, you don’t have to make your jokes about that. Now that I’m back doing stand-up and I’m back on tour, my humor is so much sharper because I’m more educated. I’m not making those stupid jokes, it’s not necessary. So, it’s enlightening for all of us, but a lot of people are resistant to it because they have benefitted from this.

Are there things that you’ve said that you regret?

No, I don’t regret. The only thing you can do is to keep pushing forward, learning more and doing better.

I’m asking that because you acknowledged that some people found Uganda Be Kidding Me offensive.

Based on the title of the book, quite offensive. The subject matter inside the book has very little to do with it other than the fact that we were on a safari in a different part of Africa. But yes, the title of the book was offensive, and I do realize, but at the time, I was like, “Why? Who cares!” Now, of course, I’m actually like, “No, actually take a minute to consider how your work is affecting other people.”

Doing this work is such a departure, you know? The last book I wrote is unlike anything I’ve written, and I was able to get real with a therapist about all these things. Doing this documentary is unlike anything I’ve really done because I’ve had a shifting point in my life where I was like, “This is not about collecting a paycheck. I am already somebody who has benefitted from extreme privilege. What am I going to do with that privilege? What am I going to do set an example for myself, for other people, and to set an example for the rest of the work that I want to do?”

You discover quite early on in the documentary that talking to people of color about white people’s problems is not the way to go in addressing white privilege. Did you have a different approach to the documentary in the beginning that changed after you went to the open mic night?

Yeah, that night was a little tough, but that was what I was after. I want it to be tough. I want to have tough conversations. I like that. I like to go into a conversation and have my opinion changed. I used to have conversations, trying to change people's opinions. And now I’ve realized that, no, I'm the one who needs to talk less. But I really like being a vehicle for that kind of uncomfortable conversation, because I think a lot of people shy away from that. And that's something that comes very easily to me. So it's not harder, it's not hard for me. I enjoy that, and that's the kind of stuff I want to do.

This documentary is ostensibly about white privilege but you frame it around your own life. Was that your initial approach to documentary, interrogating your own past and your own privilege?

Yeah, I met with a lot of directors, and I wanted to start with my own privilege because it's the elephant in the room. Alex Stapleton was starting to get in to my history, and I didn't think any of that was relevant. I told her about my experience growing up, and then my experience with my boyfriend Tyshawn, and when I moved in with my brother for a year, and she was like, “Oh my god, we haven’t spoken to him. We have to go there.” And I was like, “What does that have to do with anything?” And she was like, “That's a perfect example of you traipsing into somebody's life, at your leisure, not feeling any of the real effects of how they're living. You’re just having an interesting adventure, and then leaving whenever you feel like it. He could never visit your lifestyle or your culture in that way, and then just take off and everything would be fine.” And when I started to think about it like that, then it just became even more personal because it became a big story about my experience. So yeah, it started out that way, but I didn't expect it to continue. I didn't think it was all going to be about my own story. It was just, I think, in retrospect. It's a natural way to tell that story.

Was it difficult for you to revisit your own past and your past relationships?

I wouldn't say “difficult” is the right word. I was looking forward to it. You know, I’ve reunited with too many ex-boyfriends on these documentaries. Every director I've worked with was like, “We should meet your ex-boyfriend.” I'm like, “Look, I’m running out of them.” So I wasn't that excited to go meet Tyshawn. I hadn't seen him since I was 17 years old, or 16, maybe. I was so nervous, and I was dreading it to a degree, not because of him, but because of me. But I knew it had to be done. And I like that, you know? I really like to challenge myself. So it wasn't unbearable by any means. It was necessary. I think it ended up being one of the most moving things in the documentary. How his life was just kind of snatched away from him.

That was one of my favorite parts because I just found it really heartwarming and special. What was that experience like for you?

It was exactly what you saw. It was great. It was wonderful to see them again, and it was just like old times, except everybody was sober. His mom was a heroin addict. He was using the last time I saw them. The mother wasn't. And this was before my foray into drugs and alcohol. So I really wasn't doing anything at that time either, plus, I was like, 16. Maybe I was smoking pot... Yeah, I was smoking pot because that’s how we got caught. It was really heartwarming and it was a real eye-opener, because it was right in front of my face, and at that time in my life I wasn’t really thinking about that.

You’ve been moving into documentary filmmaking lately. Is that something you want to continue to do?

Yeah, I think I’m gonna do another Chelsea Does series, and we just have to figure out what I'm going to focus on. I just want to do stuff where I could travel and film it. We just have to figure out what that looks like.

Do you have any initial ideas so far?

I do, but I don't want to share them because we haven't sold them yet. I'm doing my stand-up tour for the next two months, and then I'll probably go into production for another project. I just have to figure out which one that is.

Is it overwhelming going back to stand-up? You took a break for a while to get into politics and activism.

Yeah, I didn't think I was ever going to want to do stand up again, quite frankly. I didn't think that that was on the list of things for me. I thought I was done with that. I burned myself out so much. But I just realized I burned myself out with everything, because I had just thrown everything at the wall, like, oh yeah, I’ll do a show, and then I'll do another show, and then I'll do stand-up, and then I’ll do a book and I'll do a tour while I'm doing the show. I never thought, “Oh, wow, you're going to burn out.” Everyone can count on me to slow down, slow down, slow down. But I got to the point where I was like, “I don't want to write a book or do stand-up ever again.” And that was like six years ago.

So finally, I sat down and went to a therapist after everything and dealt with my real shit about what happened when I was a little girl. I wrote that book because I thought, “Oh, wow, this is fascinating.” This guy gave me the tools to deal with my anger and pent up rage I had towards my brother dying and learn how to be a better, calmer, gentler person. And through that, I started doing my book tour, I had people interviewing me in different cities. And then after 10 days I was like, “This is a stand up show.” So I waited until the end of that, which was 20 cities, and then I added seven more cities just to see if I liked stand-up because I was like, “This is all just a one woman show.” And I loved it. I never thought I would love stand-up again. I really had to back myself into it, because I do love it, and I'm having the best time. I'm in Boston tonight doing a show. I'm excited to be doing stand-up again. I finally feel like I have something important to say.

What’s your favorite part about doing stand-up?

Having a narrative. Before I used to just get up and tell jokes, and now I'm telling a story. It’s the story of life, my book and my kind of awakening. Now I have a purpose to doing stand-up. I always just thought stand-up was collecting a check to be funny. And now I have a message.

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Originally Appeared on GQ