Chelsea: Too Hot to Handler

She’s hilariously inappropriate, hugely successful and happiest when she’s blonde. Chelsea Handler reveals why she’s changed her mind about marriage, what she’ll do after her show ends and how she landed bottoms up in her own birthday cake

by Leah Rozen
SPORTMAX viscose dress, 212-674-1817
Photograph: Peggy Sirota

Handler grew up the youngest of six children in a nondrinking household in the New Jersey suburbs. “I’ve wanted people to know my name since I could talk,” she says. At 16, upon learning that she was pregnant, Handler ran away to Niagara Falls with a girlfriend in the same fix. There, she tried to dye her hair red (“as if I was a famous person and the police were going to be looking for me”), but it turned bright orange. “It took us about 48 hours to realize we’re not going to make it here. Let’s just go back and tell our parents we’re pregnant,” says Handler, who ended up having an abortion. “That my hair turned orange was more of an impetus for me to go home than the lack of jobs in Niagara Falls.”

After high school and a halfhearted layover at a community college, she moved to Los Angeles at age 19, determined to become famous. Handler struggled as an actress but, after a couple of years waiting tables (“Now I’m a very generous tipper”), turned to comedy at 21 and found the track to success. She published her first book, a humorous sex memoir called My Horizontal Life: A Collection of One-Night Stands, in 2005; landed Chelsea Lately in 2007; and made Time’s 100 Most Influential People list in 2012. Today she reportedly hauls in at least $10 million annually, lives in a house in L.A.’s posh Bel Air neighborhood, drives a Tesla (“Whatever the nicest one is, is the one I got”), is pals with Charlize Theron, Jennifer Aniston and Gwyneth Paltrow and has a personal assistant who packs her underwear for trips in clear Baggies labeled fresh panties.

“The life I live now is better than any life I could have imagined,” she says. “If someone had told me 20 years ago that I was going to be able to live like this, support my family, take friends on amazing vacations and be able to run a company—I never thought of myself as somebody who could be in charge in the way that I am. All of that is possible just by really, really working hard.”

Also possible, it seems, is marriage, which Handler, who in the past dated TV executive Ted Harbert, rapper 50 Cent and hotelier André Balazs, had long ruled out. “I’m not getting married right now, but in 10 years or even five, if I met somebody I was really in love with, I wouldn’t mind being married once,” she says, adding with a laugh, “I don’t see it going very long.”

Closing in on 40 can give you that kind of perspective. Handler turned 39 in February but says, “Now I just assume I’m 40 because 39 is so close to 40.” And 40 is fine by her. “I feel like I look younger than I have in a while and act it. But I also feel more adultlike because in the last few years I know how to bifurcate my social and professional life more than I did. They used to meld and blend together, but now they are definitely separate.”

She anticipates throwing a blowout bash for her 40th birthday. So how did she celebrate her 39th? Theron gave her a ladies’ brunch in L.A. “I wanted this to be mellow,” says Handler, who was gearing up for her book promotion and stand-up tour. Instead, it turned into a girls-gone-freaky fête—and all because of a gluten-free birthday cake, brought by a friend. Handler tries to follow a gluten-free diet but owns up to frequently cheating—and Theron called her on it. “Charlize said to me, ‘Why don’t you man up and be a real woman and eat whatever the hell you want and stop eating this -gluten-free bullshit?’ I’m paraphrasing,” says Handler. “And then my friend Mary [actress Mary McCormack] said, ‘You need to pull your pants down and sit in that cake.’ So I did. And I have the evidence to prove it.”

First published in the June 2014 issue

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