A waiter approaches and she orders margaritas for both of us. In an oversized tote bag swimming with loose paper, Handler somehow easily locates pages from her forthcoming book of travel essays, Uganda Be Kidding Me. She wants to show me photos from the trip of herself and her friends peeing off the sides of various modes of transit -- a Jeep here, a boat there.
"I have 85 pictures of me peeing," she says as she takes me through the photos. "This is me peeing off a boat, in Botswana peeing off a Jeep, my sister and my cousin peeing, Sue"-- who works with her -- "peeing." She laughs. "It was crazy."
Handler is just as put together as she is crazy. The author of the memoir Are You There, Vodka? It's Me, Chelsea's party girl persona suggests otherwise, but it's hardly a secret that she has to be wildly hard-working and smart to run a talk show on E!, Chelsea Lately, that attracts more women in the 18 to 34 demo than any of her competitors on network television. Four books, three of which flew to number one on the New York Times' Best Seller list, contribute to the legend. (Grand Central Publishing gave Handler her own imprint several years ago.) When she's performing stand-up or hosting her show, she's certainly putting on a bit of an act -- but only to a degree. She really does love to drink (we both have two strong margaritas before two in the afternoon the day we meet) and she really does say inappropriate things (she jokingly refers to the bartenders waiting on us as "Asians" because they are all Asian). She really is the American Everywoman's most outrageous friend who somehow always seems to have more fun and be more fearless than you and everyone you know. You want her to be your plus-one at every event, even though you worry she might cause a scene.
Handler didn't think she'd write another book after editing Lies That Chelsea Handler Told Me, a collection of funny stories about her by her family, friends and coworkers. "It was just as much work as a real book for some reason," she says. Then, "I went on tour back-to-back for two years, which meant shooting my show from Monday through Thursday, flying out Thursday, performing, doing a book signing, two shows Friday and book signings after each, then flying to a new city Saturday, two shows and book signings at each -- it was the most insane schedule you could imagine. I was happy to do it. But by the end of it, I was like, 'I don't ever want to hear the sound of my own voice again.' Which was unfortunate because I had my television job."
But on that Africa trip, she decided to write another one. After lunch, she's headed to her publisher with notes on the cover mock-up she has in her purse. "I hate this font," she says. And on the retouching: "Can you make my arms look a little less airbrushed and fatter or more muscular?" She's confident they'll do what she says. "No one tells me what to do -- in any capacity."
Handler unabashedly enjoys all the "nonsense" -- her word for the fruits of her fabulous wealth and success--she has now. She's become so successful that -- like the state of modern celebrity -- it's comical. She's rumored on many websites to be worth $35 million. Forbes put her on its Celebrity 100 for the first time in 2010, reporting her income as $19 million with $10 million from her stand-up tour and $4 million from book advances. She didn't go to college. She held -- and was fired from -- nine waitressing jobs, which she worked from age 19 to 27.
"I was the biggest bitch," she says of her waitressing days. "I didn't understand people who wouldn't look you in the eye and tipped before tax. Do you have any idea the kind of tips I leave? How you make someone feel when they get a $100 tip on a drink?"
Even when she was waitressing and doing stand-up, she had a hard time saving money. "I would go to San Francisco and lose money on my week because you have to put yourself up at a decent hotel if you don't want to be, like, staying with drug dealers and prostitutes," she explains.
When Handler finally did get on TV, she still waited tables, but none of her customers recognized her "because I was on the fucking Oxygen network doing like a kitchen camera show."
Skirt and top by Dsquared2, earrings and bangles by David Webb and bracelet by Lulu.
She decided to write her first book, My Horizontal Life, after her friends urged her to put all her funny and outlandish one-night stand stories -- which Handler says are all true -- into a book. "I had been reading David Sedaris and I'm like, 'Well, maybe I can write discursive, essays about different things and then have a through line,'" she says. "I wrote a couple chapters and I sent it to my manager, who at the time had never read a book in his life, and he was like, 'These are really cute. You write like you talk.'" She found a literary agent who sold it to Bloomsbury for $35,000. "I called one of my friends who told me to write a book and I go, 'I just got a book deal because you told me to write a book.' She goes, 'You didn't hand in what you wrote, did you? Because we saw that and that's not a book.' I go, 'That's exactly what I handed in. You told me to do it, and then I got a book deal, and now you're not happy for me?' That was the reaction. I couldn't believe it." (She later made up with the girl.)
Now she has assistants, flies privately, lives in a mansion in Bel Air where she employs, much to her amusement, a one-armed gardener, drives a Tesla and shacks up at the Four Seasons when she visits New York, where she feeds her dog bits of chicken paillard from her plate. "Life has become so ridiculous because I have access to such nonsense and I can go to these places. I've become so infantilized by having so many assistants -- people who take care of you and pack for you and dress you. It just never stops," she says. "It's very random nonsense but I'm glad to have it.
"We stay in places based on how they make a margarita," she continues. "I call ahead and have my assistant talk to them. I'm seriously on the border of turning into Jennifer Lopez. That's what I think of myself." She counts among her close friends Sandra Bullock, whom she refers to casually in conversation as "Sandy," Jennifer Aniston ("Jen") and Charlize Theron ("Charlize"). "People are like, 'Why are you friends with her and her and her?!' I'm like, 'You guys, I have a different person on my show every day,'" she says. "That's how I date, that's how I make friends."
Handler is quick to point out that she has tons of friends who aren't famous. Like Shelly, who lives with her and whom Handler calls "my lesbian" -- the owner of one of the dogs who's joined us for lunch. They traveled with Handler on the safari and force her to leave L.A. when she needs to get work done.
"Hawaii is gross. I just went there to finish my book. My friends were like, 'Where can we go that you will fucking finish this book?' I went and I sat there," she says. "I went out on the beach the first day and there were paparazzi everywhere. Thank god the pictures were nice."
Handler never writes in her home. She wrote half of Uganda Be Kidding Me at the nearby Hotel Bel-Air. "I go there and I have to have two margaritas. There's a great quote from Ernest Hemingway and it says, 'Write drunk, edit sober.'"
Chelsea wears a dress by KaufmanFranco
You wonder where Handler's real and stage personas begin and end. She's made a career out of simply being herself, but part of her act is just that: an act. At the Paper Nightlife Awards, which she hosted the night before I meet her, she told the crowd sardined into the Manhattan nightclub Marquee that she hates Brooklyn. It's one of those things, in the age of Girls and the obsession with artisanal everything, that you're not supposed to say, which is exactly why it's funny and why Handler knew the audience would laugh hysterically. But offstage, over lunch: "I don't really hate it. I've been to Brooklyn like twice and I don't hate it. I'm sure it's probably great."
But she stops short of being disingenuous. Handler really thinks what she thinks, and she doesn't care how that makes you feel about her. For instance, she hates Fashion Week and finds fashion reviews "utterly ridiculous." "I'm interested in looking good for me, but I'm not interested in going to a fashion show. It's not real," she says. "I went once last year with a boyfriend. I was like, 'This is the worst nightmare I could have ever been to.' I was embarrassed to be there."
She also never wants to go to Vogue's annual Met Ball ever again. She attended in 2012. "I was like, 'Why am I here?'" she recalls. "I didn't have fun." The theme was "Impossible Conversations" between fashion designers Elsa Schiaparelli and Miuccia Prada.
For Handler, the whole thing was just, well, impossible.
"I have no idea what the theme was, nor did I care. I know that I wore motorcycle boots under my Roland Mouret gown. I think it was a Roland Mouret and Anna Wintour was like, 'She cannot wear motorcycle boots.' I'm like, 'Well then I'll wear them so I can guarantee never getting invited again.'"
She has plenty of projects to keep her busy anyway. She's doing a stand-up tour to promote the book this spring, as well as onstage conversations with Ronan Farrow at 92Y in New York and Gwyneth Paltrow at the Alex Theatre in L.A. And she's working on developing shows for a few fellow comedians. As for herself, she drops hints about a Netflix project but won't go into specifics. "I'm on a network that doesn't get a lot of people watching, so all my people, I'm bringing in," she says. "So if I'm doing that on that network, imagine what I could be doing where there are viewers."
With all this work, how much does Handler even sleep?
"A lot," she reassures me. "I take a Xanax every single night."
Chelsea wears a skirt and top by Dsquared2, earrings and bangles by David Webb, bracelet by Lulu Frost.
styled by Jill Lincoln for rachel zoe studio / shot at The Podosin House courtesy of Meyler & Company Locations
Makeup by Gina Monaci for Magnet Agency / Hair by Adir Abergel
Photo Assistants: Courtney Beckett and Marc Kelly / Stylist's Assistant: Alyssa Sutter