Chelsea Handler's Split Personality; May Be 'Done With This Show'

This story appears in the current issue of The Hollywood Reporter:

It's a late-March day, and Chelsea Handler is sitting behind a schoolteacher-inspired desk scribbling away on a pile of papers preparing for that afternoon's back-to-back tapings in Los Angeles of E!'s hit show, Chelsea Lately. As a hairstylist works her signature TV-worthy coif, Handler lifts her gaze momentarily and offers a reporter a drink: "We've got lemonade, and we've got water." The best-selling author of Are You There Vodka? It's Me, Chelsea, an ode to alcohol -- some would say addiction -- does not keep a martini bar anywhere nearby.

PHOTOS: The evolution of Chelsea Handler

Handler is distant but cordial. "This is my dog, Gina," she deadpans, pointing to the woman standing behind her. "And this is my hairstylist Chunk," she motions to the 100-pound brown and black mutt sleeping at her feet.

It's 1 p.m., and Handler is reviewing the two opening monologues she'll be performing and is editing blog posts writer Sarah Colonna drafted. A self-proclaimed control freak, Handler demands signoff on every decision. Her schedule fluctuates pending on her touring, but when in Los Angeles, she maintains a strict routine: 9 a.m. writers meeting; 11 a.m. workout and shower; 1 p.m. hair and makeup while editing, writing and rewriting; 4 p.m. taping.

"I have final say in everything I'm a part of, whether it's Chelsea Lately or my books and my stand-up," says Handler. "That [kind of power] doesn't happen a lot. And I didn't know it didn't happen until it happened to me and I realized I was the only one."

Something then catches her eye. It's Vanity Fair's May cover of a shirtless Rob Lowe, and her hairstylist has uncovered it on the makeup vanity. "Really, Graydon?" she says witheringly, with disdain, referring to VF editor Graydon Carter.

I inquire about the cover and ask to see it too. "Would you like a few minutes in private, Leslie?" she says with a small smile.

I can't tell -- am I being made fun of? Or is it just girls joking around? Am I in on the joke or the butt of it?

It's uncomfortable.

But that's Chelsea's charm. Isn't it?

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Later that day, there's just one hour to go before taping will begin on this day's Chelsea Lately. A production assistant enters Handler's second-floor office without so much as a knock to discuss an opportunity that has surfaced: Victoria's Secret swimsuit models. After a last-minute cancellation on Ellen, the company is looking to book three of its models (led by Adriana Lima) on that afternoon's taping of Lately to promote its new Miraculous Push-Up swimwear line.

"What would they do?" Handler snipes. "Sit next to [3-foot-7 sidekick] Chuy in bathing suits? Adriana Lima is a pretty big-time model. Wouldn't that be a little embarrassing?"

None of the three or so employees around her says anything as they await her decision. After taking a few moments to mull it over, Handler dismisses the idea with a wave of her hand.

"Tell them it's too late," she says tersely. "I don't really need Ellen's scraps." Another hint of a smile creeps across her lips.

To know Handler is to know that Ellen just got off easy. With a reputation as a grenade-throwing outsider (not too many A-listers can claim their first book was about their one-night stands) but a career resembling that of an insider, the 36-year-old comedian has engaged in headline-generating spats with everyone from Nick Cannon ("just heard nick cannon is starting a comedy tour," she tweeted in October. "Who's going to do the comedy?") to Tori Spelling ("I'm going to try my hardest not to tell her she looks like a man anymore. It's not nice. Even if it's true, it's not nice."). Late last year, the stand-up superstar -- who is in the midst of a 21-city tour of single-night engagements to promote her newest best-seller Lies That Chelsea Handler Told Me, a jaunt that will gross $6.5 million -- made gossip websites explode after scorching Angelina Jolie. "She can rescue as many babies from as many countries as she wants to," Handler said onstage in Newark in December. "I don't f--king believe you. … She gives interviews, 'I don't have a lot of female friends.' Cause you're a f--ing c--t … you're a f--ing bitch."

Sometimes, her bombshells are more personal in nature. In late May, Handler told a reporter from The New York Times that she had had an abortion when she was 16. "I'm pretty candid," she explains a few days later. "I'm not interested in hearing celebrities lie about stuff like that. I'm not proud of having an abortion, its just part of the fabric of my life. There's no reason to hide it."

Clearly, Handler the provocateur and Handler the businesswoman are two different entities. The latter, currently in the throes of contract negotiations with E!, of which she speaks openly, is not someone who makes random slips of the tongue; like any gifted comedian, Handler deploys shocking statements that only seem spontaneous, wild, dangerous. They are designed to generate the kind of attention that makes fans -- and Handler's are legion -- want to pay $60 a ticket to sit in anticipation, wondering just what in the world will come out of her mouth next. Thanks to that filterless relationship with her audience, Handler has built the rarest of creations in Hollywood: a female comedy empire (perhaps second only to Tina Fey's). Her fourth book, Lies, is resting comfortably, as of press time, at No. 3 on The New York Times best-seller list (hardcover nonfiction), and at NBC's recent upfront, E!'s new sister network announced it had ordered to series Handler's Are You There, Vodka? It's Me, Chelsea, based on her 2008 best-seller, as a midseason replacement.

Through her late-night show (which dominates the coveted women 18-to-34 demographic and has a median age of 33) and 3.5 million Twitter followers, Handler has cultivated a loyal fan base of women who love her willingness to say what everyone else is thinking. "She'll poke fun at anyone, but she's also not afraid to poke fun at herself," says Bonnie Hammer, chairman of NBCUniversal Cable Entertainment. "That makes her vulnerable, open and funny and gives her permission to do the same to others."

That freewheeling making-hay-of-everyone formula is great for late-night but is somewhat uncharted turf for a play-it-safe network like NBC. "Part of what we need to do at NBC is to get people to know that we're doing things different and a little more in-your-face," explains entertainment chairman Robert Greenblatt. He says the goal of the series is to embrace Handler's caustic barbs without driving away viewers. "I think when you get into business with somebody whose voice you like, you need to let it go out there unfettered. She's smart enough to know that she's doing a mainstream network television show and there are things she would want to do that probably don't make sense in the bigger landscape."

And there are fewer bigger question marks in cable at the moment than what exactly that landscape is. Currently, Handler is knee-deep in negotiations with E! as the clock winds down on her contract that expires at the end of 2012 (it was extended in 2009). As nearly 1 million Lately loyalists continue to tune into her top-rated talk show (her nightly ratings come in fourth on the network behind the seasonal Kardashian-themed weekly series, Kendra and Holly's World), E! is scrambling to find a way to keep Handler on its payroll, even as it looks to expand its scripted programming under Hammer. "I'm sorry that we weren't able to do Are You There Vodka? for E!," says Hammer, laughingly adding, "and so the second-best choice is to do it for NBC. At least in my mind; Bob probably disagrees." For her part, E! president of entertainment programming Lisa Berger isn't afraid to show her hand. "Our hope is that we have a long relationship and that she continues to be one of the most important faces for our network. We're working with her to craft something where everyone wins."

Still, the comedian's future with both E! and her Lately mothership, whose bread and butter remains the celeb-fueled gossip Handler admits she has grown to deplore, remains far from clear. "We'll see how it goes and if it works out for me to stick around here," Handler says, without a trace of emotion. "It's a lengthy process. They tell you you're valuable, and then you get a counter and you think, 'I guess you really don't care about me at all.' Nothing is set in stone, so if things go south, then obviously I'll be moving along."

So what would Handler -- who brought in more than $40 million in ad revenue for the network in 2009 -- do next? She says she and her production partner Tom Brunelle are weighing those options carefully as they grow their newly minted production company, Borderline Amazing. Says Handler: "I talked with Bonnie about how I see myself growing as a producer and a performer. I'm not one to plan ahead, but I don't want to be doing the same thing for five more years."

Adds Brunelle: "We're not really sure what's going to happen, but we've got 18 months to figure it out. We're never going to have a drama department; we're comedy people. We're developing plenty of shows. Whatever it is, it has to be funny." Handler has shown a knack for finding, nurturing and supporting other talent, be it Whitney Cummings or Ross Mathews, both of whom have developed pilots with Borderline.

Greenblatt says Handler "could do more for us on NBC, whether it's late-night or primetime." But Handler isn't so convinced. In fact, it's not something she even wants.

"The next step for me is not The Tonight Show," she says. That's a job for Jimmy Fallon. I'm way too divisive for a show like that."

Her definition of what is funny, though, seems to be in some sort of existential flux. "I want to do something that's going to utilize my brain a little more than this show," she says. "If Lately is the show that I'm going to do, it's going to change. But it may turn out that I'm done with it altogether. I can't keep doing the same thing; my brain is bleeding. I want to do something that's more mindful and isn't celebrity-centered. I'm not looking to totally bail on E! They've done a lot for me, and I like it here." Beat. "If you take away the Kardashians."

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"She'll poke fun at anyone, but she's also not afraid to poke fun at herself. That makes her vulnerable, open and funny and gives her permission to do the same to others." -- Bonnie Hammer, chairman of NBCUniversal Cable Entertainment

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With a bank account brimming at $22 million and seven-figure checks coming in annually from her three previous best-selling books, Handler built a fortune lambasting the very inner circle in which she increasingly resides. Her 30-minute show won fans with an original recipe: a format that includes a self-deprecating opening monologue, celebrity interviews -- which recently has acquired a higher caliber of talent, including Handler pals Jennifer Aniston and Reese Witherspoon -- and a roundtable of Handler sidekicks she refers to as "misfits" who dissect the most ridiculous celebrity gossip. After 700-plus episodes, Handler is no longer just the wry outsider. Even after she was critically panned for her September 2010 MTV Video Music Awards hosting job ("You have to be an idiot to not know that was going to happen," she says), the show nabbed its highest ratings since 2002 (11.4 million viewers), becoming the third-most-watched MTV telecast ever.

Thus Handler is now in the fantasy mode of her career -- the part where you are so rich, so successful, that you can step off the treadmill and reassess. "I want to do something people aren't expecting from me," she says. In a nod to her current employer, the woman who cites Gloria Steinem and Fran Lebowitz as role models, adds: "I want to educate people and deliver news that isn't just surrounded by Charlie Sheen. I'd like to be able to do the serious stuff in conjunction with the comedy. I'd like to make an impact and have more responsibility than I do now."

Hammer, in her first discussion of what is ahead at E!, says there will be room for what Handler is seeking. "I would say that E! is a wide-open book right now in terms of where we go," she says. "We're about to launch into what I call a brand audit, not dissimilar to what we did at USA seven years ago, to figure out what E! is right now. E! is very successful, it's not broken, but the goal is to do to E! what we did to USA -- take it from a successful channel and have it just completely break out. I'm a big believer that E! can be a top 10 cabler, maybe even top five, in the not so distant future." She adds, "As we look at where the brand can go, Chelsea may be able to play a wonderful part in that. I don't know what that means yet in terms of new formats and points of view, but we will not be going downscale but instead moving to kind of a broad, upscale, fresh tone. There are a lot of possibilities."

And so it is that Handler's show, perhaps reflective of its host's celebrity fatigue, may seem a wee gentler lately. Once the voice of her nightly roundtable that unleashes on the likes of Lindsay Lohan, Handler now acts as a sounding board -- allowing her panelists to throw the necessary punches audiences as Handler interjects with an occasional one-liner either at her own or her comics' expense.

Four years ago, Handler joked to an audience: "Katie Holmes [said] Tom's turned on by the sight of her in a suit and miniskirt. Tom also likes it when she wears the monitoring bracelet on her ankle." Would she do the same joke today? Probably.

"I only have talked about people that I think are acting irresponsibly or are making fools of themselves," she says, putting her face in front of her dog Chunk and receiving a lick on the nose. "There's no reason to talk about Reese Witherspoon. I've never talked about those people and anyone I've become friends with. I'm not going to be friends with them if they're idiots in the first place."

And in her mind, she knows who the idiots are and the distance she wants to keep from them.

"Jennifer [Aniston] said she saw the Kardashians at dinner last night," Handler says. "She was like, 'They're nice.' And I said: 'Don't get photographed with the Kardashians!' People will blame me for it!"

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Blessed with a knack for one-liners at an early age, Handler headed to Los Angeles from Livingston, N.J., at 19 to pursue an acting career. The youngest daughter of a Mormon mother, who passed away in 2005, and a Jewish car salesman father, she says: "I wanted to be famous. It's embarrassing to admit, but I came out to L.A. thinking it would happen in no time," Handler says with a snort. "I thought, 'Once they see me, they'll be so glad I came.' I always had a ridiculous amount of self-confidence about what was going to happen to me."

But like many fame-seekers before her, Handler was met with the harsh reality of Hollywood and quickly wound up waiting tables at Le Petit Four on Sunset and the old Morton's steakhouse on Melrose. After nearly three years of failed auditions and answering cattle calls ads in the pages of Back Stage West, Handler decided it was time to do something to differentiate herself.

"It doesn't hurt to be attractive, but I thought about what I could do that would give me my own voice," Handler explains. With a sharp tongue from a young age, Handler -- who enjoyed comedy as a child -- began developing a stand-up act at a friend's suggestion. "I didn't know at the time it would totally dictate my career," she says.

In 2002, Handler, then 27, landed a role on Oxygen's hidden-camera sketch comedy series Girls Behaving Badly and quickly realized her own behind-the-camera potential. "I remember knowing what would work and what would be funny, but I still had to answer to these guys," Handler recalls. "I thought, 'This is never going to work for me.' "

Handler spent the next five years angling for guest spots on series including My Wife and Kids and The Bernie Mac Show and managed a fairly stable gig as a quick-witted, hyper-snarky talking head on a variety of E! countdown shows. Eventually, Handler caught the eye of Harbert, and he plucked her out in 2006 to create an original series for the network, The Chelsea Handler Show. At the time he developed the concept with Handler, E! was floundering with reality shows such as The Simple Life 4 and Gastineau Girls.

"Immediately, Ted noticed her and felt she had this unique comedic voice," says Berger. "We wanted to try and find the right vehicle for her on our network and ended up developing a weekly show."

The show was short lived, as the network canceled the series after its first-season run and created the idea for Chelsea Lately. Around the same time, Harbert and Handler began their four-year relationship (it ended in January 2010).

Handler teamed up with future production partner Brunelle, then a producer on MTV's Your Face or Mine?, to create the 12 episodes of The Chelsea Handler Show that would evolve into her nightly talk show and where Handler would become the boss she craved to be. Chelsea Lately premiered in July 2007 and after only one year on air was averaging more than 500,000 viewers at 11:30 p.m. In February 2009, Handler moved up to the 11 p.m. slot and developed a cultlike following that averages 1 million viewers. "There are little spikes here and there, but we have pretty steady ratings," she says. "Our same audience shows up five nights a week."

Handler, whose audience is overwhelmingly female (more than 80 percent of her viewers in the 18-to-34 demo are women), has maintained steady ratings for close to two years as she holds a monopoly on the thritysomething working-woman demo in late-night.

Earlier this year, Handler and Brunelle launched their documentary-style sitcom After Lately for an eight-episode run. The weekly show followed the Chelsea Lately cast and crew re-enacting the behind-the-scenes shenanigans of the nightly talk show. One part fake, one part real, the premiere season drew more than 1 million viewers a week. E! has already ordered a second season.

Now, Handler also personally is financing an autobiographical documentary, which she hopes to take to the Toronto Film Festival, following her throughout the 2010 Chelsea Chelsea Bang Bang stand-up tour (which grossed more than $16 million). The documentary captures a vulnerable Handler as she struggles with her breakup with Harbert (the comedian lies in bed and tells the camera she's texting her ex, "You're not the boss of me anymore"). Even though the documentary catches a visibly exhausted, makeup-free Handler curled under the sheets of her hotel room bed, she maintains that she does not suffer the usual comedian demons, nor professional insecurities. "When I was starting out and I didn't have my own show, yes, I was insecure," Handler explains. "But no, I'm not insecure now. Once you've achieved success and you're making decisions that are working, I don't understand why anyone would be second-guessing themselves."

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It's another day back at Handler's office. "I flew in from New York yesterday," she says, attempting to describe the ridiculousness of her office when she arrived. "I walked in, and three people were in cheerleading outfits and another was naked with tape over them."

Handler has moved from the desk and now is sitting on the couch across from me. She has traded her Jimmy Choos for Havaianas flip-flops and is visibly more relaxed and more comfortable with my presence, here on our third day together. Now that I've withstood a few blows, I'm seemingly worthy. She continues: "I said, 'Wow, this is great. This is exactly what I want my life to be like.' "

Even with the faint stain of sarcasm in her voice, she's being genuine. That is exactly what she wanted her life to be like. I slowly begin to understand her method. She'll test and poke. And if you have the guts to come back for more, she'll slowly begin to lift the curtain. She doesn't trust easily. But once you're in, you're in (just ask her staff, who benefited from an all-expenses-paid Cabo vacation last summer).

"It was nice meeting you," Handler says. Oddly formal, she sticks out her right hand as she heads toward her maroon Bentley.

What Handler's future holds is anyone's guess. She avoids comparisons to other female comedians, even Joan Rivers, who long ago also was criticized for raunchy humor and rough treatment of celebrities. When asked her thoughts about the Rivers documentary A Piece of Work, Handler says, "I thought, 'I hope I'm not doing stand-up at that age.' "

So what will it be? She makes it clear, whatever she does, she will do it her way. "I have really strong opinions; I'll never sell out," Handler says. "I'm not going to wake up one day and have a perfume. That's never going to happen." She adds, "It would smell like rubbing alcohol."

-- Lacey Rose contributed to this report.

HANDLER'S COMEDY EMPIRE: With no signs of slowing down, Handler continues to nurture her brand and promote her own rising star

TV & Film

• Are You There, Vodka? (2012)
• Hop (2011)
• This Means War (2011)
• After Lately (2011)
• Chelsea Lately (2007-present)
• Pretty Wild (2010)
• In the Motherhood (2007-08)

Tours

• Chelsea, Chelsea, Bang, Bang (2010)
• Lies Chelsea Handler Told Me Tour (2011)

Publishing

• My Horizontal Life: A Collection of One-Night Stands (2005)
• Are You There, Vodka? It's Me, Chelsea (2008)
• Chelsea, Chelsea, Bang, Bang (2010)
• Lies Chelsea Handler Told Me (2011)

Miscellaneous

• Belvedere Vodka endorsement (2010)
• Playboy cover model December (2009)
• Grand Marshal of Los Angeles LGBT Pride Festival in West Hollywood (June 2009)