Chelsea Handler is crying. Tucked in the back corner of the restaurant at New York’s Mark Hotel, Handler is dabbing away her tears when a waitress with perhaps the most awkward timing in serving history approaches. She stands dumbstruck at the scene she just walked up to.
“He’s breaking up with me. Can you believe it?” Handler deadpans, still verklempt, gesturing with her snotty napkin across the table at the reporter she’s having brunch with. When the waitress finally walks away, she lets out a big sigh and giggles. “This is like an Oprah Winfrey moment.”
In the grand tradition of Ms. Winfrey, a long conversation about the next phase in the comedian, author, and TV host’s career has meandered through her life’s biggest milestones, striking a surprising emotional chord in the celebrity best known for doling out acid-tongued critiques of Hollywood’s most vapid tabloid mainstays.
Whether it’s in her five New York Times best-selling books, her sold-out stand-up comedy tours, or her seven years hosting the hit E! channel late-night talk show, Chelsea Lately, it’s abundantly clear to both fans and detractors of the 40-year-old performer that Chelsea Handler does not suffer fools. And fools: beware.
As she climbed the ranks, becoming not just the only female talk-show host in late night but among the highest paid people in comedy, Handler honed a brand around her very pointed, very funny comedic middle finger.
She gave it to those who found her style of comedy too acerbic, too sloppy, too edgy, or too whatever to enjoy. She gave it to the Hollywood establishment that was writing her checks, capping off a run on Chelsea Lately noted for her frequent skewering of employer E! by calling the show “seven years of ridiculous stupidity” in its final episode.
And she gives it to everyone who thought she had some responsibility to continue her run as late-night’s only woman by taking over for Dave Letterman, Craig Ferguson, or any of the other men who vacated their late-night seats in the last two years—or assumed that she would even want to.
“Annoying,” she says. “Those assumptions are annoying. Like asking me what it’s like to be a woman in late-night. Like how many times are you going to belittle me as a woman by asking me that question? It’s just like stop talking about it already. It was never an interest of mine. I was never pursuing that at all. So for everybody to be constantly speculating about it was super annoying.”
So it’s understandable that it’s a little jarring to see that middle finger drying tears on a Monday afternoon as we discuss life post-Lately over brunch. (She had a tuna burger. “Enjoy your bowl of cum!” she says as my Greek yogurt arrives.) But it might not be shocking for much longer.
“I feel like there’s a tougher exterior that’s been torn down,” Handler says about herself at one point in her new Netflix documentary series Chelsea Does, a collection of four documentaries hitting the streaming service Saturday. Consider them Handler’s own spin on Anthony Bourdain or Morgan Spurlock—cultural anthropology by way of personal exploration.
The four documentaries center on hot-button topics—Marriage, Race, Drugs, and Silicon Valley—and feature a mix of interviews (the CEO of Ashley Madison is grilled in Chelsea Does Marriage, Al Sharpton appears in Chelsea Does Race), roundtable conversations with famous friends and even Handler’s family, and confessionals by the comedian herself.
Part of a lucrative Netflix deal that also includes stand-up specials and an upcoming talk show set to launch later this year, Handler executive-produces Chelsea Does, which as she says, finds her more vulnerable and exposed than we’ve ever seen her—a tall order following her recent topless Instagram crusade.
“When you’re yourself on TV all the time, you think people are getting to know your full personality,” she says. “Whereas that personality that was being represented on my old show was very one-dimensional: ‘I’m in charge, I’m a bitch, I’m going to tell you when to shut up, and blah blah blah.’”
Enter Chelsea Does.
“This is real, and this is the full spectrum of me,” she says. “It’s me being silly, and stupid, and funny, and bright, and smart, and everything that is embodied in my personality.”
Chelsea Does Marriage, for example, finds her visiting a Las Vegas drive-in chapel, and attending a bachelorette party. Chelsea Does Silicon Valley has her pitching an app.
Chelsea Does Race has Handler traveling to the Deep South to uncover lingering racial tension, patrolling the U.S.-Mexico border, traveling to Israel, and tackling the culture of political correctness—an issue she wrote an op-ed about for The Daily Beast—by facing a firing squad of propriety police featuring representatives from the Anti-Defamation League, the NAACP, and other organizations to glean what they find offensive and why.
While happily deferring to director Eddie Schmidt (This Film Is Not Yet Rated) and producer Morgan Neville (20 Feet From Stardom) for much of the filming, Handler says she really took the lead on Chelsea Does Drugs, which has her sharing a catered meal of marijuana-infused food with friends and spending a night on camera after mixing Ambien and alcohol.
But even then she didn’t entirely get to do or show everything she wanted to do. Because it was illegal.
“I was like, ‘Let’s do mushrooms! Let’s do cocaine, to show everyone what it’s like being on coke!’” she says. “They were like, ‘That’s illegal!’ But they let us go to Peru and do ayahuasca. What network is going to say yes to that? Only Netflix.”
Does Handler have an agenda, or at least a perspective guiding her fact-finding mission? Of course, and that’s sort of the point of Chelsea Does.
“I’ve never ever had the feeling ever, to be like, ‘Oh my god I want to be in a wedding dress. And I want to walk down an aisle,’” she says in the early minutes of Chelsea Does Marriage, for example. “Like that to me is nausea-inducing. But I’m questioning things about it that I never did before.”
Handler has been in serious relationships. A long-term boyfriend she had while she was in her twenties is interviewed in Chelsea Does Marriage. She dated Ted Harbert, who oversaw E! as the former CEO of Comcast for nearly four years, and afterward was attached on-and-off to hotel manager André Balazs for two years.
She also briefly dated rapper 50 Cent, a curio that will likely follow her to the grave.
“I know, and we only dated for two months,” she says, rolling her eyes. “It’s, like, mentioned in every article. It’s so funny. It’s probably more annoying to him—actually, he probably loves it.”
There’s an obvious fascination about Handler’s personal life given her own admitted public candor about it—one of her books was called My Horizontal Life, after all—but also because of her views on marriage. What Chelsea Does Marriage does, however, is make a distinction: Just because she doesn’t want to walk down the aisle doesn’t mean that she doesn’t value a partner and commitment.
“Before I think my problem with marriage was that I didn’t want to do anything that was expected of me,” she says. Making through the years of when-are-you-going-to-get-married-and-have-kids? needling felt like a victory lap. “When I turned 40 I was like, ‘Look! Not married! Not divorced! No kids!’ Just like I said I wanted to be.”
Now that she’s made it to that 40-year-old milestone, her feelings about have gotten a little more complicated—and somehow clearer, too.
“I was like, OK, now the pressure’s off,” she says. “Now I would do something, because it’s unexpected. I would do it if I met somebody. I think I was pairing the showcase of it, the whole pageantry of weddings, with commitment rather than realizing they could become two separate things.”
Not that she’s aggressively in the market for someone now.
“My mind’s not even there lately,” she says. “When you do something like these projects that are so fulfilling, I’m like, ‘OK, what can we do next?’ My friends are like, ‘Do you want to meet this guy?’ and I’m like, ‘Not really.’ If I’m going to meet them I’ll meet them when I’m supposed to.”
She lets out a big laugh: “Like all of a sudden I believe in fate.”
If not fate, partnering with Netflix was certainly kismet for Handler. To see her treating the streaming service as a haven of sorts shouldn’t shock anyone who sensed her very palpable exasperation with making fun of celebrities on E! for seven years. She didn’t exact conceal it. In fact, she aggressively vocalized it.
Handler landed her late-night gig in 2006, after years of working the Los Angeles stand-up circuit and making a quiet mark in the Oxygen network hidden camera show Girls Behaving Badly. She had reservations when E! wanted to reformat a weekly sketch show she was hired to star in into a daily wrap-up of TMZ tabloid stories, a genre she loathed, but leaned into the series with her own acerbic sense of humor.
It quickly became one of E!’s highest-rated programs, turned Handler into one of the most recognizable figures in Hollywood, and, over the course of seven years and more than 1,000 episodes, eventually made her miserable.
“I didn’t want to be there,” she begins, saying that it was around the fifth year of Chelsea Lately that she ran out of enthusiasm. “Everyone was annoying me. My staff was fighting about who was going to be on air all the time. They were catty. I was like, ‘This is so childish.’”
Still, a sense of responsibility for the staff she employed, even if they got on her nerves, guilted her, in a way, into keeping the show running—until she realized how ridiculous it was to make decisions based on that.
“So I think the last go round, I didn’t even really decide,” she says. “I just said it on Howard Stern, like, ‘Yeah, I guess I’m not going to do that again,’ and I figured that since I had thought it I had already said it.” (Former staff members have said they were blindsided by the announcement.) “I was just like, ‘That’s a wrap on this.’”
Chelsea Does serves a bridge between what she used to do on Chelsea Lately and her new show that will debut on Netflix later this year. “It’s not going to be a talk show that you usually see,” she says, apologizing that Netflix has forbidden her from revealing more specific details. “It’s not going to be a late-night show. I’m done with that. I’m not doing that again.”
And at the very least, Chelsea Does proves that anyone who judged Handler based on the celebrity-focus of Chelsea Lately has been underestimating what she’s capable of. “I hope so,” she says. “I think I underestimate myself.”
As she tells it, each phase of her career seems accidental. But each memory is accompanied with a quip about what hard work it was.
“When I start something new, I’m like, ‘I wonder if I can write a book.’ All right, let’s do that,” she says. “‘I wonder if I can write another one.’ Let’s do it. And I also kind of feel like, the book stuff I’m done with right now. I don’t care about that. Stand-up I’m done with. Been there, done that. I’ve done as much as you can do as a stand-up. And I did it so much, four huge tours, that I got good at it and I’m done. I want to get good at other stuff.”
In the year and a half since she’s been off TV, she briefly wondered if, after at one point verging on overexposure, she had become irrevelant. It was a fleeting thought when, as hard as she was working on Chelsea Does, she relished a break from it all.
She was exhausted from flying to the next comedy tour stop on Thursday nights after taping Chelsea Lately. She took a breath. She bought a house in Spain, and learned Spanish. She spent time with her family without feeling the pressure of work in the back of her mind. “That was important.”
She remembers when she graduated from high school, the youngest of six kids to a Jewish father and Mormon mother in New Jersey. All of her siblings had gone to college. Her father told her it would be a waste of time to do the same—in the loving, we-know-what-your-future-holds way—suggesting that she head to California instead.
She waited tables while auditioning for random acting jobs and doing stand-up on the weekends. She was broke—for a very long time—relying on her parents and siblings to send her money. Still, they never doubted that she was going to make it in an industry where almost no one does.
“I thought my family was going to be like, ‘Fuck, when are you going to get a grip and get a real job?’” she says. “But they never once did. I’m 26, borrowing money and waiting tables, partying, not having my act together. But they never once said, ‘Get your shit together.’ And thank god they believed in me because I don’t know if I would have.”
Understanding her connection to her family is key to understanding Chelsea Handler. When she was 10, Handler’s brother died while he was hiking the Grand Tetons, a formative experience for the baby of the family and something that, over the years, fiercely bonded the Handlers together.
Then, in 2006, Handler lost her mother, Rita, to a battle with breast cancer. “I grew up at that moment,” Handler says.
She returned from her book tour in London to be by her ailing mother’s bedside, arriving aghast that no one in her family was capable of handling the situation. “I was the only person that could be like, ‘Let her die! She doesn’t want to be remembered like this.’”
There was a woman smoking in the bed next to Rita’s, and her brother and father were just sitting there. “My mother just looked at me because I was such a fucking shit-kicker,” Handler says. She cursed out the nurses, got her mother a private room, screamed on her behalf when she needed more morphine, and slept on a cot next to the hospital bed for the next 10 days.
“My brother was like, ‘Oh my god. I’ve never seen you take charge,’” she says, her voice cracking as her eyes well with tears. “I was like ‘It’s because you guys aren’t being responsible. She’s dying. Let her fucking die.’” She grabs a napkin and starts dabbing her eyes.
“I can’t believe I’m crying about this, it’s not even noon,” she laughed before continuing her story.
“At my mom’s funeral, my brother gave this beautiful eulogy. It was so beautiful. He’s such a great public speaker. And you know, we’re all in our own worlds. And he said about me and my sister, ‘I’ve never seen my two kid sisters grow up right before my eyes. They’re both women now.’ And he’s right. I stepped up and was not the kid and became an adult. And it was a beautiful time. Even though it was tragic, it was beautiful.”
When the startled waitress who stumbled on a celebrity crying over her tuna burger walks away and Handler makes her joke about me breaking up with her, I bring up how she’s so often characterized in Chelsea Does by the people in her life: strong, intimidating, powerful, abrasive. That’s not all of what I’m seeing. Does she wish other people saw the other things, too?
“When you’re a woman and you’re forthright, people are like, ‘Oh, she’s a bitch.’ Well then, I’m a bitch, you know?” she says.
“But everybody is a bunch of different things. You can be a bitch and be wonderful. You can be a wonderful bitch.”