Chelsea Handler: Funnier Than the Boys

It's not easy, making Chelsea Handler laugh. As the host of Chelsea Lately, the E! Entertainment network's late-night talk show, the stand-up comedienne and best-selling author is as dry as a Belvedere martini. Sitting across from guests like the soon-to-be-incarcerated rapper T.I. or one of a squadron of Kardashians, she fires off questions in her big, sandpapery, Jersey-girl voice and barely cracks a smile. Her guests, on the other hand, are downright giddy. It could be because they don't often hear a petite and pretty blonde talk about flushing a "shadoobie" down the toilet, or they aren't used to fielding such incredibly frank and, yes, hilarious questions in front of a studio audience. Then again, it could just be their nerves. Handler, 34, may be one of just two women (the other is Mo'Nique) in the testosterone-heavy 11:30 time slot, but she's earning a reputation as its toughest and most original interview.

While the fellas of late night are busy giggling at their own jokes and getting into trouble with their "assistants," Handler delivers shockingly astute, tweezer-sharp commentary on the dubious culture of celebrity (on E!, no less). As a result, she's racking up a steadily growing audience in the coveted 18-to-34 female demographic.

"I'm into politics, and I love watching the heavier news magazine shows," Handler says. "But let's be honest. I'm on E! It's not what I do, and it's not what my audience wants."

Handler and her writing staff, which includes four other women and five men — a fairly gender-neutral ratio in the notorious boys club that is comedy writing — gather around a conference table at 9:30 every morning with a stack of tabloids and Web page printouts from gossip sites. In a matter of minutes, the room turns into a raucous shoutfest of jokes, each a little grittier than the last. The goal: to make Handler smirk, even laugh, and to write some of the freshest and most outrageous comedy on television.

Handler arrives at the studio office wearing white cutoff gym shorts, running shoes, a Kelly green Nike jacket, and a white baseball hat with a ponytail peeking out of the back. Chunk, her recently adopted rescue dog and frequent subject/guest on the show, is trotting along beside her. The walls of the hallways, the writers' room, the cubicles, the writers' offices — virtually every vertical surface — are plastered with photos.

In the writers' conference room, the staff has gathered with their morning coffee. None of them eat, except for Handler. She's snacking on a grapefruit the size of her head (she keeps a giant bowl of them in her office/dressing room) and a bowl of sliced turkey.

Handler is calorie conscious, but she has a well-chronicled weakness for vodka — her second book of first-person essays, which came out in 2008 and held a solid spot on The New York Times nonfiction best-seller list for 14 months, was titled Are You There, Vodka? It's Me, Chelsea. There are no fewer than 10 unopened bottles of the stuff in her office. For years, she's called out Grey Goose as her favorite brand, but she recently defected to Belvedere because "a friend told me that Belvedere has zero sugar in it, and that's all I needed to hear," she says. "So I called them up, and now Belvedere is sponsoring my upcoming comedy and book tour this spring."

Her third book, Chelsea Chelsea Bang Bang, hits stores in March. She will take a brief hiatus from taping the show and embark on a 23-city stand-up tour to coincide with book signings and appearances. It is in front of a live audience that Handler feels most at home.

After moving to Los Angeles at 19 and working the comedy-club circuit (she made the esteemed Montreal Comedy festival at 24), Handler got her big break in 2002 as one of the four hosts of Girls Behaving Badly, in which young female actors pulled public stunts and pranks for hidden cameras. In 2006 she launched The Chelsea Handler Show, a weekly half-hour sketch-comedy series that lasted for two seasons. But it wasn't until Ted Harbert, president and chief executive officer of E!, approached Handler about a talk show that she considered being a late-night host.

"I never really saw that coming," she says. "I didn't become a comedian to work this hard. But Ted, my boyfriend, who was not my boyfriend at the time, was saying, 'You need your own show. You have such a strong point of view.' But the only way I was going to be on E! was if I could make fun of E! and everyone on those shows. I thought, That would be a great job."

The first topic of discussion in the writers' room this morning is a public-service announcement airing on CBS that encourages men to give their wives or girlfriends Pap smears for the holidays. A round of jokes about diamond necklaces in vaginas don't impress. Then Handler suggests making up a list of the various gifts she's gotten over the years, including an STD test and an ultrasound. After a little riffing among the group, they land on a gag about finding a lost iPhone in her uterus, which eventually makes it onto the show.

"I love a stupid joke, something that doesn't make any sense," Handler will explain later. "And things that come out of left field I find very funny. The challenge is to keep it fresh. If you're talking about Britney Spears over and over, it's very hard to keep that interesting."

A lesser item on the agenda is the birth of former Hugh Hefner girlfriend and E! star Kendra Wilkinson's baby, a 9-pound, 5-ounce boy. "Which makes him bigger than Ryan Seacrest," says Handler, without even looking away from her citrus. Sarah Colonna, a writer/comic on the show, says, "Hef was contacted for comment, and he said, 'Where am I?'"

The women of Chelsea Lately have a unique and seemingly authentic bond. They're all stand-up comics who often join Handler on her tours. That they have penetrated this traditionally all-male domain and that, even more surprisingly, the five of them are actually friends, is unique. Once a week, they meet downstairs for a group pilates session, courtesy of Handler. Heather McDonald, another writer/comic on the show, turned up to exercise one day in what she describes as "the ugliest running shoes in the world."

"Chelsea saw them and said, 'Those are ridiculous. You can't wear those,'" she says. "I took them off for pilates, and Chelsea was texting her assistant about something. By the end of class, she'd come down and replaced my shoes with a brand-new pair in my size."

"When you're doing stand-up, there are usually five or six men and maybe one woman on the bill," says another woman on the show, Jen Kirkman. "Many women just don't want to see another woman around. They don't want to share the attention. Chelsea's not like that. She's really supportive."

After the 90-minute session in the writers' room is over, the writers retreat to work on the material they pitched, and Handler heads to the editing room for 10 minutes. Then she's off to the gym for her daily hour-long workout. By 12:30, she's back in the office, showered, in a red velour robe, and into hair and makeup in her office, which is really more like a studio apartment. There's a sofa, a mini fridge, a food scale, an ice machine, and a makeup table; racks of tailored, colorful, dressy-casual clothes that show off her tiny, athletic frame; and shoes — lots of them — from Lanvin, Miu Miu, and Yves Saint Laurent. The hairstylist stands behind Handler, who's checking e-mails at her desk, with a curling iron. A staff writer comes in with a rough outline of the night's program, including all of the material written while Handler was working out. While having her makeup applied, she checks off which lines will make the cut. Minutes later, a production assistant comes to fetch Handler (with half-done hair and no lip gloss and still in her robe) and her dog to film promo-teasers for upcoming shows in the studio downstairs, which she improvises on the spot.

Handler names Jennifer Aniston, Jenny McCarthy, and Jim Carrey as her favorite all-time guests. "I haven't heard of anyone who's been unhappy with how they were treated on the show. At least it hasn't made it back to me. But I don't make fun of people who lead respectable lives. Like the Reese Witherspoon and Jake Gyllenhaal breakup — I won't talk about them because they seem like smart, decent people. But if you go out and behave in a ridiculous way, you should expect to be made fun of."

Next, Handler heads to the editing room to punch up a sketch about giving employee reviews, while eating a jar of pickles, then back to hair and makeup to finish before the 2:30 taping.

On the show today is an Animal Planet host named Dave Salmoni, who's brought along with him a lemur, a wolf, and a giant South American reptile, which Handler proclaims would make her take a "giant shadoobie" if she saw it in the wild. Adam Lambert from American Idol is in to film an interview for an upcoming show, to whom Handler says, "You used to be hugely fat in high school, right? And your hair isn't really black. You're a redhead. So you were just really unlucky." Lambert thinks it's hilarious.

By 4:45, Handler's whirlwind day has ended. On most days, she's wrapped and ready to go home to the condo she shares with Harbert in Marina del Rey by 6 p.m. "To be honest, my favorite part of the day is when we're done," she says. "The day is always really busy. We're all friends, and I like the writers. It's like summer camp that just keeps going. But I like it to be over. I like the minute when I can get off the stage and go home, and I know I've done a good job."

Christine Lennon is a writer in Los Angeles, where she lives with her husband and two children.