By Ben Lyons
Photographs by Andrew Southam | May 27, 2011 | People
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Trying to track down Chelsea Handler is no easy task. Not because she’s reclusive or overly private—far from it, in fact—but because she’s that busy. Her nightly talk show, Chelsea Lately, continues to be a ratings monster for the E! Network, which just picked up season two of her scripted comedy series After Lately. This past April, she appeared in the number one movie, Hop, alongside Russell Brand and James Marsden, and can be seen this winter as Reese Witherspoon’s best friend in This Means War. On the heels of her successful book and comedy tour, Chelsea Chelsea Bang Bang, she’s about to hit the road on yet another tour, this time called Lies Chelsea Handler Told Me—though, she insists, “this tour is only eight weeks, and I’m not adding second shows because I just don’t care. I’m spending more time in New York, and I’ll definitely be out in the Hamptons this summer.”
While today the Livingston, New Jersey, native may spend her summer sipping vodka martinis on the East End or sailing on a yacht she’s renting with friends in Croatia, growing up her parents would spend the season in Martha’s Vineyard. “My parents have a summer house there,” says Handler. “This will be my first experience with the Hamptons.”
Hamptons, be forewarned.
Honing the Handler Empire
I manage to get Handler on the phone one morning and ask where in the world she might be. You never know with her. Earlier in the year, she took her late-night show down to Australia for a week, and last year she did just shy of 80 stand-up dates across the US. While I’m expecting her to be on the move, she simply states, “I’m just sitting here, trying to act like an adult.” I explain to her what the interview is for, to which she replies, “Oh—I thought this was for Esquire. I’m so stupid.”
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She can’t be too stupid, or else she wouldn’t have been able to build her very own media empire. “You must be confusing me with Ryan Seacrest,” she points out. But it’s true: In addition to her hit TV shows and sold-out stand-up tour, her previous books, My Horizontal Life: A Collection of One-Night Stands; Are You There, Vodka? It’s Me, Chelsea; and Chelsea Chelsea Bang Bang all found their way onto The New York Times’ best-seller list, with the last two reaching number one. That’s why she isn’t too concerned with how her most recent book will fare.
“You don’t have to be number one every single time,” says Handler. “As long as you’re in the game, you don’t have to be at the top of the game.” Lies That Chelsea Handler Told Me is written by her friends, family and coworkers, and as Handler puts it, “It’s about different ways I’ve screwed them over, because I get bored a lot.”
A Stand-Up Support
She seems to have a true love-hate relationship with the company she keeps. For example, E! News correspondent Michael Yo, a frequent guest during the nightly roundtable on Chelsea Lately, recently embarked on a stand-up career of his own and has said he looks to Handler as a mentor.
“Well, that’s embarrassing,” she says. “He sent me a note with flowers saying, ‘Thank you so much for allowing me to do stand-up. I have my first show this weekend. I would never have been able to do this without you.’ And I thought, Oh no! Don’t involve me in your stand-up career. Don’t ever mention that to people. Ever.”
Josh Wolf, Heather McDonald and Brad Wollack, other regular guests on her talk show and series regulars on her sitcom, will go on tour with Handler this summer, doing 20 minutes each of stand-up and participating in a panel Q&A at the end of every show. Despite giving them their big breaks in the business, Handler doesn’t seem too keen or quick to sing their praise.
“I like underdogs,” she says. “I like people that don’t belong on television. There’s no way anybody would put Brad Wollack on television. I think it’s hilarious to put my brother on TV; there’s no way in the world that someone would put my brother on TV. I like putting people like Chuy [Bravo, her personal assistant on Chelsea Lately] on. I like saying ‘Screw you’ to everybody that thinks there is one way to do television. I think it’s hilarious to put people that are not attractive on TV. I surround myself with people that I find really funny and really kind of stupid. So if I get joy out of it, I have to assume other people are getting joy out of it. There are a lot of girls out there that are just like me but not as obnoxious about it.”
Enter the Celebrities
She doesn’t rub shoulders with just her fellow comedians or immediate family members anymore. Hollywood’s A-List can be found five nights a week on her couch getting more candid than they might on other late-night talk shows.
“I just had Gwyneth Paltrow on the show. She was hilarious talking about her grandmother calling her a name that I don’t think anybody has ever heard Gwyneth Paltrow use, which I thought was amazing because her timing couldn’t have been more hilarious,” she recalls. “I love Jennifer Aniston. I love any girl that comes on and has fun and isn’t self-conscious about what she says, because it’s not that serious. I don’t get in trouble a lot for what I say because people are used to hearing me say it, but if you’re a really big celebrity and say something that I would say, you get so much heat for it. It shouldn’t be that way. You should be able to say whatever you want as long as it’s not malicious or racist. As long as you’re joking around and it’s kind of innocuous, it’s OK.”
|Dress, Proenza Schouler ($1,525). Jeffrey New York, 449 W. 14th St., NYC; jeffreynewyork.com. Peretti earrings, Tiffany & Co. ($1,395). 53 Main St., East Hampton; tiffany.com. Bangles, Susie Fox ($3,600 each). London Jewelers, Americana Manhasset, 2046 Northern Blvd.; londonjewelers.com|
After years of paying dues and fighting her way into the conversation, Handler is as relevant as ever to the fans across the world who have always loved her, as well as the Hollywood community that has finally accepted her. Even the hip-hop community loves Chelsea.
“Rappers are great interviews because they just don’t really care and they are willing to say anything,” she says. “And I love that because that’s kind of how I am. They all hit on me. I love Pharrell and thought he was really sweet; Nelly, too. P. Diddy was the only one I was like, ‘Get away from me.’ He’s so late all the time—maybe he won’t show up in the Hamptons until summer is over.”
Styling by Julie Matos
Hair by Lona Vigi for The Magnet Agency
Makeup by Gina Monaci for Chanel and Bumble & Bumble
Photographed on location at Loews Santa Monica Beach Hotel
July 21, 2016