Chelsea Handler Is Ready to Try Something a Little More Serious

UNICODE Photo: Graeme Mitchell

The scrapbook on the dining-room table is unexpected. You picture Chelsea Handler in her free time enjoying vodka on the rocks, maybe, but never fussing with photo tabs and mounting tape. Yet here are the supplies, and scattered around are photos: a black-and-white one of Handler at dinner with BFFs Sandra Bullock and Mary McCormack, another of a younger Chelsea holding a cigarette and standing leapfrog-style over a friend. It is only 11:30 in the morning, after all.

Do you do a lot of crafty things?

Handler makes a face. It’s not as stony or derisive as the one she directed at an obsequious wedding planner, or the guy who runs a historic South Carolina plantation with the aim of “not making slavery more horrific than it may have been,” in Chelsea Does, the four-part documentary series that just premiered on Netflix and explores various fraught topics from marriage to racism. But the meaning is clear.

“Do you think I do?” she asks. “No, I’ve been working on that scrapbook for almost a year and a half. I was fucked-up stoned one night in my room, and I was like” — fake-slurring — “‘I’m going get all these pictures together.’ I still don’t know what the fuck to do. I’ll never finish it.”

It’s for a friend. The 40-year-old comedian has a lot of them, some dating back to high school and others more recent: Sarah Silverman, Jennifer Aniston, Gwyneth Paltrow. Just don’t call them a squad. “What is that word? Why do I keep hearing it?” she asks. Instagram, Taylor Swift, every woman Taylor Swift has ever met. “That sounds stupid to me.”

The former host of Chelsea Lately is not one for trends, even those that align with her feminist impulses. She specializes in sexual braggadocio and is unafraid of being mean, which brings her public persona closer to that of Howard Stern than Gloria Steinem. She doesn’t run an organization to inspire young girls (like Amy Poehler). She doesn’t publish a newsletter (Lena Dunham). She doesn’t give Ms. speeches that go viral (Amy Schumer). “I like to be involved with anything that supports women, but I think, like, actions speak louder,” she says. “You look at somebody’s body of work rather than listening to them talk about it.”

As for hers: Handler has filled five best-selling books with confessions that most people would prefer to censor, whether it’s her extreme fascination with little people or her unapologetic love of alcohol. From 2007 until 2014, she brought a shambolic but candid approach to late night, curling up on a chair opposite her guest and casually maneuvering her way to the gossip that mattered, sometimes surprising them with her forthrightness. She once asked Drake what was up with him and Nicki Minaj “in a penetration context,” and lightly mocked Justin Bieber on multiple occasions. Biebs even pulled the curtain back to complain that she was asking questions about his dating life that had not been vetted beforehand (as is customary in late night).

This impression Handler gives of going off-script, or of never having one to begin with, is what draws fans to her. She seems like someone who would be friends with Schumer’s character in Trainwreck up until the moralizing “I’m broken” ending. To those fans, that’s honest. To her detractors, it’s brash. The overlap in that Venn diagram seems to be exactly where Handler wants her comedy to be. Apologies are permanently off the table; political correctness is the enemy, which is how Chuy, her beloved little-person sidekick on Chelsea Lately, ended up dressed as Hitler to celebrate Germany’s World Cup win.

These days, though, making people laugh is not necessarily enough, and even the term p.c. is outdated. Lately, there’s room — arguably, a lot of room — for earnestness in comedy, especially among the critical darlings. Aziz Ansari grapples with taking his immigrant parents for granted in his Netflix series Master of None. Schumer imbues nearly all of her show’s sketches with straightforward feminism. Even Louis C.K. occasionally makes being a middle-aged white guy feel profound. So it’s probably no coincidence that after eight years of working on her E! late-night show, Handler was ready to tackle her most ambitious, socially aware project to date, even if she can’t refrain from delivering a few what did she just say? shocks along the way.

“I think it’s just responsible, as an entertainer,” says Handler. “We’re not saving lives or anything, but if you’re going to be in this business, then you should want to be as interesting as possible, and make interesting choices, and keep it compelling.”

It’s January, and we’re in her Bel-Air home, an expansive, well-appointed property: white walls, neatly arranged atlases, a coffee-table book as tall as a toddler mounted on a music stand and opened to a Dolly Parton spread. The camel-colored dining chairs are covered in some type of coarse hair that feels poky when you sit on them. “I don’t do anything for myself,” Handler says. “My whole fucking house is controlled by an iPad, and I can barely turn on the TV.” (She addresses this in the series’ tech installment, “Chelsea Does Silicon Valley.”)

Several segments of each hour-ish-long documentary unfold here, with Chunk and Tammy, her loyal part–chow chow companions, perambulating in the background, observing their owner, much like they do now. A couple of months ago, for instance, Handler chased an Ambien with vodka to show what happens when a person stays awake on that combo (in this case, she’s awful at Twister, feels judged by her pets, and doesn’t remember any of it the next day). It’s one of the milder scenes in “Chelsea Does Drugs” — later in that installment, Handler learns her friends were once so concerned about her recreational drug use that they considered an intervention, a scene she swears was not rehearsed for the cameras.

“I was like, ‘What? No,’” she says, and her gravelly laughter echoes across the backyard. She’s invited me to join her poolside on more comfortable wicker furniture, and she sits with her knees pulled to her chest. She’s dressed down, even more casual than the plainclothes she tends to prefer for stand-up tours: a baseball tee and some ripped jeans.

Handler admits in the series to having done a lot of drugs but never thinking she had a problem — to which, in the “Drugs” episode, The Mindy Project’s Fortune Feimster, a frequent panelist on Chelsea Lately, responds, “Isn’t the person with the problem always the last to know?” It’s a format that anchors each documentary: Handler sits down with friends and colleagues for frank, topical conversations, Dinner for Fivestyle, which then launch into more personal explorations, some of which touch on sex, her childhood, and her many, many opinions — like that marriage is stupid, or that she believes being equal-opportunity in her humor by hating on everyone insulates her from accusations of racism. Family members make several appearances, mostly so that Handler can grill her dad, a former used-car salesman, about her upbringing, his various prejudices, and his sexual proclivities.

Handler grew up the daughter of a Jewish father and a Mormon mother. The youngest of six, she was forever angling for attention. When their parents had company, her brothers would often tie Chunky — that’s what her mom called her, thus inspiring her dog’s name — to a chair as a party trick and slap her repeatedly in the face until she laughed so hard she peed her pants. “For some reason it was like being tickled,” says Handler. She sits up, animated by the memory. “And my mom, I remember, was like, ‘You’re encouraging it. Stop it. This relationship is completely out of control.’ And my father would go, ‘There’s nothing we can do. She will never listen to anybody.’”

At 19, Handler decided to skip college and move from Livingston, New Jersey, to her aunt’s house in California to try to be an actress. “Do you know how hard it is in this business?” Handler recalls her aunt saying. “You’re not pretty enough. You’re not skinny enough.” In 2002, she was cast in Oxygen’s prank series Girls Behaving Badly — finally she could get paid for putting herself in outrageous situations. Next came the first of the five books, My Horizontal Life: A Collection of One-Night Stands, and her own show on E!.

“It was a real tonic to watch, because late-night tradition has always been very tidy, and she’s not tidy,” says McCormack, who became close with Handler after appearing on Chelsea Lately to promote her USA series In Plain Sight. Now Handler lives down the street, and sometimes McCormack comes home to find her reading the New York Times on the couch, with a fire going.  She adds, “She’ll tell people they’re full of shit right to their face.”

But if you’re famous in part for being unafraid to say bad things about celebrities, becoming a celebrity yourself is kind of an occupational hazard. “I’m like, Who am I going to make fun of now?” Handler says. “I became friends with everybody.” Even reliable targets like the Kardashians crossed over. (Khloé sits at the “Silicon Valley” dinner table.)

And so, when it came time to figure out a next move, “I wanted to do something as far away as possible from what I was doing,” says Handler, who called it quits at E! in August of 2014 after months of suggesting publicly that she was not at all happy during the twilight year of her eight seasons of the show; she once likened it to being “in a wheelchair with no wheels.”

She declines to go into the specifics of her frustration. But despite the fact that at one point Handler was working on her nightly show, the mockumentary After Lately, and a short-lived NBC sitcom starring Laura Prepon, Are You There, Chelsea? — as well as doing book signings and weekly stand-up tours — it was fairly easy to be only peripherally aware of her. By the end of its run, Chelsea Lately was capping out at about half a million viewers per night, which is a fraction of what the Jimmys do. She often gets treated as a parenthetical — once literally, in a 2014 New York Times article about The Tonight Show hand-off (“Bullish on Boyish”) that briefly referred to Handler as the only female late-night host. She responded with an op-ed in the Huffington Post that concluded, “My only goal when I started this show … was to offer viewers another voice to end their day with (even if my show is on E!). That's the appropriate use of a parenthetical.”

Handler pulls loose threads of denim from the hole in her jeans and drops them on the patio. “Everybody running that network was so fucking dumb, and I didn’t respect them,” she says. She pauses. “I mean, they weren’t dumb. That’s so harsh to say. But, you know, they just didn’t know what to do or how to do anything. [At Netflix,] I feel like, Wow, I’m not the smartest person in the room.” She bursts out laughing again. “No offense to everybody I used to work with.”

Yes, she says, “that’s a wrap on Chuy,” and no, none of this has anything to do with her 2010 split from Ted Harbert, former CEO of Comcast Entertainment Group, which oversaw E!. (Handler is single at the moment.) Nor was she interested in the duck-duck-goose of the network late-night circuit, no matter how badly it needs a dose of diversity. “I don’t want to fill someone else’s shoes,” she says. “And that’s such a boring format. Oh, we heard you got a puppy. Who gives a shit?”

Instead, Handler inked a seven-year deal with Netflix, of which the docuseries is just a jumping-off point for a half-hour talk show. It starts filming in May, and will grapple with bigger issues and feature more out-of-the-studio moments. “I just said, ‘Listen, I’m up for anything,’” she told director/executive producer Eddie Schmidt (This Film Is Not Yet Rated) and executive producer Morgan Neville (Twenty Feet From Stardom), both of whom came up with the format for the docs and shot them consecutively, starting in the spring of 2015, so that Handler’s experiential arc with each subject was genuine. “I want to be a fish out of water. I want you to push me to do stuff I’m not comfortable doing.” This includes meeting up with an ex she hasn’t seen in two decades, confronting a white supremacist, going on blind dates arranged by clueless matchmakers, and ingesting the hallucinogenic brew ayahuasca in Peru and enduring the bodily excretions associated with it.  

“I can make a fool of myself easily,” says Handler. “I don’t have an issue with that. The drugs one was not flattering at all. But it’s real.”

This idea of warts-and-all realness is valuable to Handler, as are substances — in the Sliding Doors sense of things, she might not be here today if not for the latter. When she was 21, two years after moving to Los Angeles, Handler was arrested for drunk driving. Her court-mandated DUI class required sharing the transgression with the rest of the room, a prospect that terrified her until she stood up and started cracking jokes about having accused the arresting officer of racism (he was also white). “The guy running the class was like, ‘Okay, this is not a stand-up routine,’” Handler says. But it was, sort of. Acting consisted mainly of waitressing, anyway — comedy, she realized, could be “a last-ditch effort.”

Handler is one of those people who insists she always knew she was going to be famous. To the mean girls in high school she said, “One day I’m going to be something really special.” When her ex Peter, the one who returns in “Chelsea Does Marriage,” wound up in bed with two women a mere 12 hours after they’d ended things, she promised him he was going to be “so pissed he broke up with me.”

“I think [Peter] still wants to sleep with me, but that’s not going to happen,” she says. “And then those girls all showed up over the years at, whatever, Radio City, and they’re like, What’s your life like? I don’t know if that was the impetus for everything. But revenge is never what you want it to be. It’s silly.”

Chunk starts barking at a landscaper, which inspires Tammy. “Tammy, no! No! No!” Handler yells in varying octaves. “She’s such a follower.”

Before breaking into stand-up, Handler crashed at her aunt’s “shithole place” in Bel-Air and drove her nine cousins to school every morning, commandeering the radio to listen to Howard Stern. Recently, she found an old card from her mom dating back to those early broke days. “She wrote, ‘Dear Chunky, I’m sending you this money with all the love I have in my heart because I know one day you’re going to be rich and famous and you would do the same for me,’” Handler says. Her eyes get glassy — her mom passed away eight years ago from cancer. “It’s so sweet.” 

Often, whenever her mom comes up, so does her oldest brother, Chet. When Handler was 10, he died in a hiking accident. “It was like a vacuum,” she says. “I didn’t know what to do. All of a sudden the attention was gone from me. No one was there for anyone else. It was awful for all of us.” She’s had to tell this story so many times, she tends to speed through it. “So when my mom died, I was like, This is the worst way for the person, and the best way for the family,” she says. “You know that they want to go.”

Ultimately, her mom’s prediction about her daughter’s future success came true. Two years ago, Handler bought her aunt a new house in the Valley. She grins: “I was like, ‘I’m fucking skinny enough now, bitch.’”

Here’s a short list of people who have demanded an apology from Chelsea Handler: Beyoncé fans (for comparing Bey’s 2010 Grammy dancing to a Clydesdale); Little People of America (for Chuy, and what they see as her treatment of little people in general); Nick Cannon (for tweeting, “I just heard nick cannon is starting a comedy tour. Who’s going to do the comedy”); internet commenters outraged that she would use the hashtag #miscarriage to caption an Instagram photo of a poorly chopped pomegranate on Pregnancy and Infant Loss Remembrance Day (which she did not know existed); Serbia (for calling the country a “disappointment”). With Chelsea Does, that list is bound to grow.

“I’m sure I’m going to get a lot of shit,” she says. “I always do.”

Take, for example, “Chelsea Does Racism.” Somewhere in the middle of the hour, at dinner with Margaret Cho and actor-comedian Aasif Mandvi, Handler confesses, “This is not going to be a popular thing to say, but honestly, if Muslims are primarily the people blowing up planes, then I would like them to be searching Muslims before I get on a plane.” Mandvi pushes back to say that nobody paints in such broad strokes when Christians commit crimes, but Handler gets the last word, and it’s usually a joke (in this case, she quips that Klansmen should absolutely be searched, too).

“I’m not proud of that opinion,” says Handler. “I know it’s not right. But I don’t want to worry about offending people. Bullshit political correctness is more racist than anything, because nobody’s saying anything real. We’re all racist without even trying to be.”

Elsewhere, she sits down with representatives from various media-watchdog groups to address the age-old issue of who can joke about what and why. Guy Aoki, of Media Action Network for Asian Americans — whom some may remember for taking Sarah Silverman to task on Bill Maher’s Politically Incorrect 15 years ago — chastises Handler for making fun of Pax Jolie-Pitt. “I was like, ‘Okay, I get it,’” she says. “I wasn’t going to apologize, but it might make me think about if I’m going to make fun of a little kid. [I wanted] to illustrate the difference between a joke and something with malice. Saying black people are late is not the same thing as shooting a black person in the back. Let’s just everybody calm down.”

She meets with the family of Walter Scott, an unarmed black man who was fatally shot by police. She grills Southerners who maintain that slavery wasn’t all bad. She talks to a guy who supports building a wall on the U.S. border with Mexico. “She honestly wants to understand how people think,” her director Schmidt says. “And that’s different than just coming in and making jokes or hiding behind a character. She’s going into that situation as herself.”

Engaging with more serious subjects is probably going to surprise fans who tune in expecting her to make fun of people and talk about shadoobie (Handler-speak for poop), and she realizes that. “But I think we’re all growing up,” she says. “This for me is, I’m going to college and Netflix is paying.”

And access to a certain kind of fanbase hangs in the balance. For all the exposure Handler’s had, she’s noticeably absent from some communities: She’s not in the Apatow inner circle, or hosting Saturday Night Live, or starring in summer comedies. Not that she necessarily wants these things. “Let people who are good at acting be acting,” says Handler, who had a modest part in the 2012 Reese Witherspoon comedy This Means War.  

But is there anybody she admires? “Daniel Craig and Rachel Weisz. I’m always curious about people who stay out of the spotlight.” Okay, but anybody whose career she envies? “There’s always a level of competitiveness,” she says diplomatically. “Sometimes you see something, and you say, ‘I wish I could have done that,’ or, ‘I wish I had that opportunity. Why are they getting so much attention?’ But there’s room for everybody.” She’s insistent about not having a forebear who’s influenced or inspired her, but not even a peer whom she enjoys now? I throw out names: Amy Schumer? Aziz Ansari? Bill Maher? “I love Bill Maher,” she says, finally. “I love political humor. I love that he has such a severe point of view.”

HBO’s Real Time With Bill Maher is probably the closest in sensibility to Handler’s plans for the new talk show: celebrity guests, roundtable discussions, topic-driven episodes — except where Maher’s show airs once a week for approximately 30 weeks per year, Handler plans to do her show thrice weekly for about 90 episodes in total. It’s ambitious, which suits her go-go-go personality (both Schmidt and McCormack commented on the pace of her reading list alone, which currently includes Madame Bovary). But with Netflix, she has the opportunity to share her own point of view, and reshape her brand in the process. “I’m still me, but I just wanted broader subjects,” says Handler. “I want people to get information in a cool way.”

Still, taking an 18-month leave of absence is always a risk, and Handler was all too aware of it. “I felt insecure this year,” she says. “When you’re on TV every night of the week and then you’re out of the limelight, coming back is like reentering the atmosphere. I was like, Do people even care about me?

Whether or not they do, they’ll see a different side of her. Judgmental and sarcastic, of course — when she spars with Ashley Madison founder Noel Biderman in “Chelsea Does Marriage,” you wouldn’t want anything less — but her personal interrogations reveal vulnerabilities, too.

“I never really thought about how I was coming across,” says Handler, who admits she even saw herself differently afterwards. “When I watched the marriage documentary, I was like, Oh my God, she’s sweet. I feel bad for her.”

McCormack elaborates. “The thing is, Chelsea’s the biggest mush in the world,” she says. “She does everything at, like, an 11, including being a really, really great friend. If I’m crying, she starts crying. That’s not what comes to mind when people think of her.”

Given the acrimonious divorces, and one conscious uncoupling, among her close friends, it’s no wonder Handler started off our conversation saying marriage “makes no sense.” She also ended it by saying the opposite.  “My opinion is so easily changed,” she says. “I won’t rule anything out. Now that I’m able to separate the commercialism from the commitment, I would be open to getting married. But I have such a great thing going that I would be fine without ever being with somebody again.” She waits a second to add the beat that you know she can’t resist: “Obviously, I’d like to get fucked, so it would be nice to have sex with somebody at some point.”