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Comedian Whitney Cummings: Bewitching, brazen and with jokes to make you blush

By Dan Zak
Washington Post Staff Writer
Wednesday, December 8, 2010; 9:50 PM

IN BALTIMORE -- "I don't know how long you have to be on cable TV before they start bringing you takeout menus," says Whitney Cummings, prancing around the greenroom in faux-diva mode before her set in a group comedy tour.

"What, you're too much of a snob for deli meats?" says fellow comedian Brad Wollack, forking some curled slices of roast beef.

"Brad said she's the hottest thing in L.A.," offers Whitney's mother Patti, shutting the mini-fridge and opening a can of diet Red Bull backstage at Rams Head Live.

"Oh my God, Mom, this is so embarrassing," Whitney brays. Patti takes a sip and shrugs.

"Yeah, I guess I did say that," Wollack says. "She's very popular right now. She's blowing up."

Whitney Cummings, who was born and raised in Georgetown, and her tourmates are all regulars on "Chelsea Lately," the late-night talk show on E! hosted by comedian Chelsea Handler. In January, Cummings will film a test episode of a show to follow "Chelsea." She's done "The Tonight Show" twice this year. She and "Sex and the City" creator Michael Patrick King have written a sitcom pilot that's awaiting a buyer. She's hosting MTV's New Year's Eve special with the cast of "Jersey Shore," a high-profile if dubious gig that will render her a household name (in the houses of tube-glued teenagers, that is). She's written her own pilot for an NBC sitcom tentatively titled "In Between," starring herself as a woman who's afraid of marriage. If it's picked up, she will be one of two female creator-writer-actors in a network sitcom. The other is Tina Fey.

And screenplays are coming her way. Problem is, all the characters are a certain type.

"I open up the script and in the character description it says something like 'Claudia: a volatile [rhymes with witch],' " Cummings says, removing her flapper hat, shaking out her raven mane, revealing sculpted eyebrows and Vermeerian cheekbones. "And she's like an insane whore who [bleeps] everyone. Do I give that off? I guess it's the roasts."

It's the roasts.

Over the past year, Cummings's most visible gig has been her appearances on Comedy Central's roasts, wherein bloated icons of pop culture (William Shatner, Bob Saget and so on) are subjected to ridicule by a stable of B-list comics (Lisa Lampanelli, Gilbert Gottfried and so on). Cummings has stood in front of David Hasselhoff, Joan Rivers and Quentin Tarantino and incinerated them with flaming barbs that are unprintable here. Suffice to say they involve grotesque analyses of the roastee's private parts, with kickers invoking Jim Crow and T-cell counts that stunned even the coldest members of the Friars Club, into which she was inducted last week in New York.

"A lot of people consider me edgy, and definitely the topics I talk about are taboo," she says. "I'm talking about porn, I'm talking about relationships and sex. But I don't really curse. What I'm doing now, people will look back in 20 years and not think it's edgy. I guess it's just contextual."

Except she does curse. Often. Onstage and off. She can't place a takeout order -- salmon, shrimp and extra broccoli -- without ornamenting it with invective. Otherwise, she's clean as a whistle: She's off sugar, wheat and caffeine, since she equates being a good comedian with being a super-fit athlete. She's tall and bony, with traces of gangliness remaining from her high-school basketball prowess. At 28, she's the youngest comedian on the "Chelsea Lately" tour but thinks she looks 50. Which makes sense, she says, given all the traveling, all the late nights. But someone once asked who did her cheeks.

"I was like, 'What?' " she says. "If I was gonna get plastic surgery, do you think that's where I'm gonna start?"

She points to her breasts with rehearsed self-pity.

If there's a stereotype of Georgetown girls it might be that they are beskirted, quick to blush, proper to the point of dullness. The very opposite of a Friars Club inductee. And while she grew up in rowhouses on tony streets near Dumbarton Oaks, while she was bookish at Holy Trinity School and studied with the sons and daughters of diplomats and World Bankers at St. Andrew's Episcopal School in Potomac, Cummings does not exactly exude Georgetown.

"Women always start dirtier because you try to neuter yourself," Cummings says of her first stab at stand-up, five years ago. "The dirtier I am, the tougher and less feminine I'm gonna come off. I think I just tried to, like, pass as a guy."

This hasn't stopped the populace from classifying her in the pop-culture cohort bodaecious hilaerious, or Hot Chicks With Filthy Mouths, for whom Handler is the current mother superior. (Cummings is "unique and memorable, and someone that has a long career ahead of her if she makes the right decisions," Handler writes in an uncharacteristically bland e-mail. "Her own show is the next obvious step, and of course, I wanted to be involved in that.")

"The only thing I'm selling here is comedy," says Cummings, who did runway and catalogue modeling in high school and college. "When people bring me onstage, it's my biggest pet peeve when they say, 'And this next comedian is beautiful, you're gonna love her.' I'm like, 'What?' That's not even a variable. There's not an inverse relationship between funny and pretty. You can have both."

Exhibit A. Handler, whose comedic persona might best be described as "sardonic-feminist barfly."

Exhibit B. Sarah Silverman, who mashes together "Jewish American Princess" and a 6-year-old's fascination with scatology.

Cummings wants to be Exhibit C, the Samantha Jones of stand-up, the sexy, swaggering smart aleck who busts people's body parts.

She's working overtime to expedite her own arrival. Last year she skipped out on the "Chelsea Lately" Christmas party to do a set at the Comedy Store, Wollack says.

"She works really hard," Wollack says. "It's like, knock it off, Whitney."

"Does that make me a loser?" Cummings asks, almost earnestly.

"Yes," Wollack says. "What are you chasing?"

"It's not what I'm chasing," Cummings says, fetching a Fresca from the fridge. "It's what I'm running from."

She jests. There are no apparent demons, save for her obsession with overachievement (which is very Georgetown). Her parents divorced when she was 5 -- hence the sitcom alter ego who doesn't want to marry her boyfriend -- and her mother raised her and older sister Ashley in relative comfort padded by free lotions, perfumes and clothes from Bloomingdales and Neiman Marcus, for whom Patti was a public relations manager (her father is a venture capitalist).

Cummings, who interned for WRC (Channel 4) and studied acting at the Studio Theatre, resisted the temptation to jet to Los Angeles right out of high school. Instead she got a communications degree from the University of Pennsylvania in just three years and enlisted an agent who directed her to MTV, which cast her in the 2004 season of "Punk'd." She moved to Hollywood intent on being an actor but paid the bills by hosting countdown shows on E! and VH1.

In 2005, a friend told her she should do stand-up.

"And I was like, 'Huh,' " Cummings recalls. "It had never entered my mind, but I realized at that point everything I'd done in my life led to being a stand-up." The obsession with current events, the women's studies and communications classes, the rejection endured while doing theater and modeling, the hosting of various TV shows -- the lessons learned are the building blocks of a comedian. Timing and timeliness, personality and punch.

Before she even performed her first set, she landed super-manager Barry Katz after a spirited off-camera repartee with one of Katz's clients, comedian Jay Mohr, when they met by chance at the Sundance Film Festival.

"I never saw anybody give it back to him like that," Katz says. "It was like an unranked tennis player going up against Nadal and taking him to a new level. At the end Jay took me aside and said, 'Barry, I know this is something I've never said to you before, but that's somebody you should work with.' "

Cummings moved into a "Melrose Place"-style complex near the Comedy Store on Sunset Boulevard, and for two years auditioned relentlessly during the day while bombing during late-night spots around town. She wrote 20 pages of jokes on spec for Comedy Central's roast of the rapper Flavor Flav, which got her a writing spot for the roasts of Saget and then Cheech and Chong and then a chair on the dais for the roasts of Rivers, Hasselhoff and Tarantino.

Of all the mouths on the dais, hers was probably the dirtiest. But vulgarity is simply the current language of comedy, says Rivers, who calls Cummings "smart, outrageous and fearless" and sees no danger in being beautiful and coarse onstage -- as long as you're (a) relevant and (b) funny.

"Please, if Hitler came back with 20 good minutes Leno would say, 'Come on the show,' " Rivers says by phone. "Funny is so asexual, truly. Someone's either funny or not. Comedy is all about surprise, and to have a very pretty girl walk out onstage and then be funny and clever -- that's a double gift to the audience."

"Okay, the first thing I would do is take the phrase 'dirty mouth' and replace it with 'truthful mouth,' " says Michael Patrick King, who conducted a "Scarlett O'Hara search for the new funny female voice in comedy" to collaborate with and decided on Cummings based on a script she wrote. "The world is very loud now, very noisy. So the voice maybe needs to get a bit louder. She's still talking about classical themes like relationships, like Phyllis Diller did, only she's in the gear that the world is moving at now -- she's just adding the word 'balls,' or whatever."

She taped her one-hour special "Money Shot" at Sidney Harman Hall in the spring, and her traction keeps growing. But insecurity is proportional to the size of the venue. With two sitcoms and a talk show in the works, the venue -- and the stakes -- has never been bigger. Her roasting of Rivers was a "holy [bleep]" moment in her career, her manager says, and she now must constantly raise the bar to stay hot.

Tommy Morris, talent coordinator for the Comedy Store, has never seen anyone work harder and views Cummings as more intense than Handler and more feminine than Silverman.

"She's already made it, in a way, but Whitney needs about two more years to really get somewhere," Morris says. "She's going to continue to mellow into herself and start writing from a different perspective. She can be critical of men, but we still love her because she's not a man-hater, she's a man-observer, and she looks like she could actually get a date. She's exploding because of that relatability. There's never been someone like that before."

"Someone dropped off a birthday present for you," says tourmate Sarah Colonna, after finishing her own acerbic set.

"My birthday is in September," Cummings says.

"This brunette girl dropped it off," Colonna says, handing over a card.

"Oh, see, more small boob jokes," she says, reading it. "I can make them, but you're not allowed to. 'Have a very happy birthday, a year that's perfect too.' She replaced it with 'a very happy birthday, I have small boobs too.' It's funny when I say it, sad when someone else says it."

"What is this?" Patti says.

"Mom, don't," Whitney says, continuing to read the card. " 'Assuming I won't be able to form complete sentences when I meet you, I thought this would be the best way to let you know how much you've inspired me. I recently started doing stand-up in Northern Virginia. . . . You're one of my biggest idols. . . . It's awesome to see a female comic native to the area gain so much success.' "

Cummings pauses. "I paid her to do that," she says.

By 9:30 she and her tourmates are waiting in the darkened wings as comic Chris Franjola finishes his set. Cummings guffaws as Franjola riffs about pinkeye and feces. Then Wollack takes the stage to introduce her.

"She's young, she's beautiful -- "

"I [bleeping] hate that," Cummings whispers, rolling her eyes, then bounding up the ramp, ponytail swishing, into the blue glare of the spotlight, in front of a balcony brimming with young women who will hang on every epithet.

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