How Chelsea Handler Turned the Private Into Profit

Chelsea Handler Art Streiber / August

Chelsea Handler is onstage at a New Jersey concert arena, complaining about one of her politically incorrect pet peeves: names African-Americans give their babies. (Other things the blonde, blue-eyed equal-opportunity offender tells the audience bug her: Russians, Asians, the Kardashians, and Angelina Jolie.) She mimics a fan at one of her book signings, who complained when Handler misspelled her daughter’s name. “You spelled it wrong! It’s B-a-i-l-e-i-g-h.” To which Handler snapped: “Look, bitch, you spelled it wrong. If you’re going to name your daughter after a liqueur, at least have the courtesy to f--king spell it right.” Don’t even get her started on people who use numerals in their names, like the woman she met named L’4sha. “Can you imagine having sex with someone with a number in his name?” Handler says as she sticks out her butt and moans, “Give it to me, 50, give it to me!” It’s a clever wink at the rumors that she’s dating the rapper 50 Cent. The crowd goes insane.

For Handler, the personal is not only public; it’s profit. In just under a decade, she’s gone from a stand-up comic touring the nightclub circuit to a full-fledged brand—call it Chelsea Inc.—with books, TV shows, concerts, movies, and sponsorship deals that raked in a reported $20 million last year alone. Her act—think Joan Rivers’s irreverence, Howard Stern’s prurience, and Chris Rock’s rage—hasn’t changed much, but her fan base, which is largely women and gay men, doesn’t mind. Their insatiable appetite for her stories of sexual mishaps and other personal humiliations keeps her first two books on the bestseller list. (Together they’ve sold 1.7 million copies and counting.)

Handler is currently touring in support of her third release, Chelsea Chelsea Bang Bang. She recently signed a deal with Grand Central Publishing to head up her own imprint, Borderline Amazing; the first title, Lies That Chelsea Handler Told Me, is a collection of essays by family and friends and comes out in May. NBC is developing a sitcom based on Handler’s second book, Are You There, Vodka? It’s Me, Chelsea, and the comic is working on After Lately, a behind-the-scenes program to follow her Chelsea Lately talk show on E! Between all this, she found time to host the 2010 MTV Video Music Awards, film This Means War with Reese Witherspoon, and voice an animated role in the film Hop. Katie Couric, who is friendly with Handler, calls her “the hardest-working girl in showbiz.”

Yet unlike Tina Fey or Jon Stewart, Handler is not a darling of the media elite. She rarely appears on magazine covers. She’s never hosted Saturday Night Live (though a Facebook group is lobbying for this to happen). Her books aren’t reviewed by The New York Times. And when they do notice her, critics are unkind. After Handler hosted the Video Music Awards, the Times called her performance “among the worst in the show’s history.” The New Yorker described Chelsea Lately as “too sloppy by half.” “It’s like she’s a certain radio station,” says her friend Jenny McCarthy, the former Playboy model turned actress. “If you tune into that frequency, she’s huge, but people who don’t tune in don’t connect.”

Handler claims to enjoy having a lower profile than some of her counterparts. “I like being a bit under the radar,” she says over dim sum the morning before her New Jersey show. “In terms of income, I probably have a lot more than most everyone in my business, so it is interesting ...” she trails off.

Part of the reason Handler isn’t embraced by critics may be her refusal to wrap air quotes around her sexuality. On Saturday Night Live, Maya Rudolph, Amy Poehler, and Kristen Wiig have lampooned overtly sexual female characters: think Rudolph’s drunk, orange-skinned, libidinous Donatella Versace. By contrast, there’s nothing ironic about Handler’s sexiness—lots of cleavage, lots of heels, and the frequent assertion that her pubic hair is waxed in the shape of the E! logo. In publicity shots, she often has a hand on a cocked hip and a come-hither smile—a pose Fey might adopt, but only with one eyebrow satirically arched.

In her books and onstage, the comedian’s tales of sexual encounters gone awry mix bathroom humor with putdowns of her partners. Her former boyfriend Ted Harbert, CEO of E!’s corporate parent, Comcast Entertainment Group, has been the butt of numerous jokes: Handler’s routine includes a bit about how she smeared chocolate cake on the sheets while Harbert was in the bathroom with food poisoning. (He did not react well to the prank.) She claims to have a sexual obsession with midgets, and likes to fondle her dwarf sidekick on Chelsea Lately, Chuy Bravo.

Handler calls herself a “hot mess,” but hers is a controlled explosion. She says she has no patience for starlets like Lindsay Lohan who flash their “hot pockets,” and points out that the number of successful assignations detailed in her first book, My Horizontal Life, is in the single digits. Though much of her comedy trades on her party-girl persona, Handler’s work ethic and knack for monetizing her peccadilloes (Belvedere Vodka sponsored her latest tour) suggest otherwise. In fact, she says her busy schedule means she’s usually in bed by midnight.

It’s unclear if her fans get the nuance. During her show in New Jersey, a drunken young woman repeatedly interrupted a riff on Angelina Jolie (Handler expertly humiliated the fan into shutting up). After the show, the train to New York City was filled with knots of girls proudly discussing such Handleresque topics as “blackout sex.” But if Handler herself were to have blackout sex, she’d likely make her partner sign a nondisclosure agreement—and then spin the experience into a special for E! (She confirms to NEWSWEEK that she’s now dating 50 Cent, a.k.a. Curtis Jackson, saying that “he’s sweet and not a thug.”)

Handler grew up in New Jersey, the youngest of six children. Her mother was a housewife, and her father sold used cars. When she was 10 her oldest brother died. “The whole family dynamic shifted,” she says. “My dad went nuts, and I kind of got lost in the shuffle.” After high school, she moved to Los Angeles and wound up doing what every other wannabe does in Hollywood: waiting tables. It wasn’t until she told the story of a drunken driving arrest in a court-mandated DUI class and got laughs that she realized there was another way to get the audience she craved.

Handler launched her E! talk show in 2007 and initially featured quasi celebrities like MTV’s Tila Tequila, on the premise that they were more likely to match her level of candor. But as Handler’s profile has risen, so has the caliber of her guests, and now she books the same stars who make the rounds of Leno and Letterman. Her approach remains more Howard Stern than Oprah, and it can be fascinating to watch polished, platitudinous stars like Gwyneth Paltrow and Demi Moore adjust gears to match Handler’s style. When Jennifer Aniston appeared on the show, the normally circumspect actress volunteered that she had dated a Mormon once, which meant “no sexy time” and “no vodka.” (Aniston and Handler’s friendship has since become fodder for the tabloids: the two went to Cabo San Lucas together over Thanksgiving, and when a video of Handler calling Angelina Jolie a “home wrecker” and a “c--t” went viral last month, tabloids were abuzz with speculation that the comedian was helping her new BFF get back at Jolie.)

“She’ll never be Chelsea Plugged unless she shows up on Sesame Street,” says Couric. But the comic, whose contract with E! expires in 2012, may be ready for a reinvention. “I can’t keep doing this show forever; it’s too stupid,” she says. “It makes your brain melt.” At times she has expressed interest in doing a serious, topical show or taking her program to a major network. “We’re both not really sure where she’ll be in five years,” says her business partner Tom Brunelle, who declines to confirm reports that she’s been offered a network spot already. When asked about rumors she might replace Jay Leno, Handler deadpans, “I don’t really know if The Tonight Show is the wave of the future.”

Paradoxically, the woman who has built a small industry around her outsize personality says what she really wants is to move offstage. Handler, who is 35, says, “The whole idea is to get the hell off camera by the time I’m 40.” It’s impossible to know if this is another put-on (she’s also said her next goal is to buy a dolphin), though she is already developing shows for several of the comics who are regulars on Chelsea Lately. “It’s a happy gravy train,” Handler says, “and it’s happier when everyone’s getting a little bit of the gravy.”