“We microdosed LSD and skied. It was a whole production!”
It’s not the average way to celebrate turning 50, but Chelsea Handler is not your average woman. For the past five years, the comedian has stripped down to her bikini — and sometimes less — to ring in her birthday on the slopes. This year she invited more than 20 women to join the ski run at Idaho’s Soldier Mountain, which she documented on social media.
The party didn’t stop there. On her actual birthday, Handler released her seventh book, “I’ll Have What She’s Having,” her sixth No. 1 New York Times bestseller.
“I’m at a place in my life where I try not to put that kind of pressure on myself,” she tells The Times. “I wanted to make sure that even if it wasn’t No. 1, that I would be grateful and gracious and not be so competitive with myself or with others. To find out that it was No. 1 when I had accepted that it may not be was the best news.”
She rounded out the momentous day by doing press and appearing on talk shows, complete with live studio audiences singing “Happy Birthday” and cake in every greenroom.
“This is a really manipulative way to spend your birthday if you need attention,” she laughs as we ponder how she will possibly top it next year.
Lest you think Handler is slowing down, on Tuesday she releases her third Netflix comedy special, “The Feeling,” which overlaps thematically with “I’ll Have What She’s Having.” (One viral story she shares in both is about her one-time would-be hookup with disgraced former New York Gov. Andrew Cuomo, who is now running for mayor of the city. “I’m all for giving people a second chance” is her attitude toward his race.) In it, she talks about her childhood in New Jersey — itching to be released from that stifling existence to become her fully realized adult self — and hilariously relays exploring what felt good to her prepubescent body.
“Who were you before the world really besmirched you? When you were untouched and unscathed? When you haven’t had your heart broken or been disappointed or experienced a big tragedy yet? Who were you then? That’s really the essence of who you are,” she says of her motivation for the special.
“Looking back was very meaningful to me because I realized [that] I wasn’t cultivated, I didn’t become this woman — I was born this way. Even when I was a little girl, I could not wait to be a woman and live this life. I was like, ‘Get me out of this body and let’s get this party started.’ I wanted my own house, I wanted my own staff, I wanted to live in a big and loud and brave way.”
She’s certainly achieved all of that, and she’s pleased to have done it single and child-free.
“I’m so proud of myself for never falling into getting married or having a baby when I know those things aren’t natural to who I am,” Handler says. “I am valuable without a husband. I’m a queen with or without a husband, and so are all women. I firmly believe that.”
Jenny Mollen, an actor and writer whom Handler met on the set of the 2006 comedy “Cattle Call,” agrees. “She always knew what she wanted.”
“If it weren’t for Chelsea, I don’t think I’d have the career that I have. I don’t think I’d be an author,” Mollen says. “There were so many things that I wasn’t afraid to do because I watched her do it first.”
Still, Handler is no nun, and she’s had another sexual awakening in later life.
“When you hit your 50s, you return to who you are, you start caring a lot less about what people think, and you’re also much more present. The past is not a preoccupation like it was in my 20s; worrying about what I’d done, if I’d said something to embarrass myself. I do that less often so there’s less to be regrettable about.”
Pop culture is embracing older women’s sexuality as well, with the recent proliferation of age-gap rom-coms. “I might go down that road too,” Handler laughs, referencing who we might see her step out with next after breaking up with fellow comedian Jo Koy in 2022 and recently being linked to actor Ralph Fiennes.
For now, though, she’s busy promoting her book and special, and coming off her third consecutive year hosting the Critics Choice Awards. “I love making fun of celebrities and getting drunk with them afterward. It’s kind of the perfect evening for me,” she says of what keeps her coming back to that particular ceremony.
“In 2025, the easiest way to get a late-night talk show as a woman is to get the creators of ‘Hacks’ to write a fictional story about it,” she joked in her opening monologue about the continued dearth of women in late-night.
“Hacks” star Hannah Einbinder, one of the many female comics Handler has opened doors for, says Handler is her “own personal Deborah Vance: a fabulous blond stand-up comedian who I look up to and admire.”
Fortune Feimster worked as a writer on “Chelsea Lately” in her first comedy job when the rest of the industry wouldn’t give her a second look.
“Nobody really knew what to do with me because I was different and that was not considered a positive at the time. People did not embrace uniqueness as much as they do now,” says Feimster. “Chelsea was the person who was seeing what was different about people, and how that was an advantage and a positive thing. She saw something in me before most people and I’m so grateful for that.”
Handler also is gearing up for a Las Vegas residency. She will perform monthly until 2027 at the Chelsea at the Cosmopolitan, which was a “no-brainer” for her since the “low-commitment” schedule meant she didn’t have to uproot her life in Los Angeles to move to Sin City. She’s the first female comedian to have a residency at the venue.
“I’ve made that casino lucky,” she says, noting that every time she’s had a gig at the hotel, she and her friends have won big when they’ve gambled afterward. “Come and find me and play as close as possible to where I’m playing!”
Handler’s breadth of projects satisfies her desire for human connection.
“I love people, I love interpersonal affairs, drama between family members or [in] relationships, fractious conversations within a family or workplace dynamic,” she says. Her long-running podcast, “Dear Chelsea,” allows her to “touch base with real people. I’m a real person, no matter how famous I have become. I’m from New Jersey. I’m salty and I want to get down to business with people. The podcast has been a surprise gift that I’ve really loved doing.”
Though she writes in “I’ll Have What She’s Having” about how difficult she found hosting her eponymous Netflix talk show in 2016 and 2017 after her confidence was shaken, she’s not opposed to doing something like that again if the right opportunity presents itself.
“I like doing that job,” she says. “I like regurgitating the news, I love regurgitating pop culture. I’m one of the best people that can do that. It’s one of my strengths. I’m quick, I’m sharp, I can retain information and I can spit it back out and distill it for people.”
And although the political landscape is more fractured now than it was back then, Handler is galvanized.
“Women are not going anywhere. That’s why men are so scared of us, because we have become so powerful and so independent. The repercussion of #MeToo was Roe v. Wade being overturned. Men were like, ‘Oh, you think you’re going to tell on us now? Let us remind you who’s really in charge.’ Our whole political landscape is a repercussion of #MeToo, of Black Lives Matter, of us standing up and voicing what becomes intolerable. Our government right now is a death cough of white supremacy.”
Still, though, she’s an optimist by nature.
“I’m not losing hope. This is a moment in time, this isn’t the rest of time.”
