Why Do So Many Pretty Female Comedians Pretend They're Ugly?

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Phyllis Diller was among the first to show us all that women could, indeed, be funny—but they'd have to give up their looks, smarts, and accomplishments first.

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AP Images; NBC

After Phyllis Diller died this week at the age of 95, many an obituary fondly remembered the comedienne for her big laugh, her ou­trageous hair, her cartoonishly hideous outfits, and the refreshing, unceremonious manner in which she brushed aside the expectations of what was previously off-limits for women to joke about.

But there's one superlative Diller earned that's only been hinted at in the days since she passed: She may be the only woman ever deemed too sexy for Playboy.

Yes, that's right. The comedienne posed for the lad mag--as a gag, she would later explain--in the late 1960s. Playboy's editors thought it would be funny, she said, and what better way to get a laugh than by sending out seductive centerfold photos of a hilariously tacky, impressively unsexy woman? It seemed like a foolproof plan.

There was, however, one problem: Diller, who had long obscured her figure with the trademark ill-fitting lamé dresses she often wore onstage, turned out to have a shapely, sexy physique--and a pretty face, too, under all her clownish makeup. To everyone's bewilderment (except maybe Phyllis Diller's), Phyllis Diller was a bombshell.

So, as the legend goes, the startled Playboy execs scrapped the photos, deeming them too sexy for their comical purposes, and the pictures were never published.

Diller was a performer who built a career out of making fun of her supposed unattractiveness. "A peeping Tom threw up on my window sill," she once told an audience. She also targeted her own social and sexual ineptitude; her decrepit, aging body; and her failures at traditional femininity. "My cooking is so bad my kids thought Thanksgiving was to commemorate Pearl Harbor," she famously quipped.

But obituaries have brought to light this week that the real Diller--the offstage, offscreen Diller--was not only an attractive woman, but also a gourmet chef, a painter, a pianist, and a shrewd humorist who crafted almost all of her own material.

Diller's reign as the frumpish, clumsy queen of the underbrag was groundbreaking on many levels. She did, after all, prove that women with bad hair, bad cooking, and loud mouths could be America's sweethearts, too. She was an iconoclast, a refreshing antidote to the June Cleavers and Harriet Nelsons that had been dominating pop culture in the years prior. But Diller's trademark brand of hapless, self-deprecating, ugly-girl humor was based an invented set of shortcomings she didn't actually have. Which highlights a weird glitch in the system that still plagues women in comedy today: Why can't funny women be hot? Or accomplished? Or smart? Why do so many women with these otherwise highly valued traits have to downplay them to get laughs?

Diller was one of the first to disguise her sex appeal for the sake of her comedy, but she wasn't by any means one of the last. Many beloved female humorists, both now and in the past, have made the deliberate choice to highlight their un-sexiness in the interest of being funny.

And there's a disturbingly simple explanation for that. "You can't have people look at you and listen to you at the same time," says Gina Barreca, a professor of English literature and feminist theory at the University of Connecticut, with a laugh.

According to Barreca, young, attractive female comics in the stand-up industry have always been targets of sexualized heckling. Even today, "They still have people screaming at them, 'Take your clothes off!,'" she says, "or "'Shut up and show me your tits!'" Realizing this, Diller cleverly diverted masculine attention away from her looks by making herself ugly. "She took herself out of the sexual marketplace," Barreca explains.

Today, Diller's most recognizable heir apparent in the "attractive-woman-with-a-homely-comedy-persona" tradition may be Tina Fey. A disciple of Diller's, the 30 Rock star remarked in her 2011 essay collection Bossypants that her her pre-makeup, wet-haired self resembles "an uncooked chicken leg," and professed that when left to her own devices she clothes herself like she's "here to service your aquarium." And her 30 Rock character Liz Lemon, a high-powered, frequently frazzled TV showrunner who's somehow always losing at her own game, is often put down, even inadvertently, by her colleagues for her appearance: "Lemon, the grown-up dating world is like your haircut," sighs Jack, Alec Baldwin's corporate condescender-in-chief. "Sometimes, awkward triangles occur."

And yet, in the spring of 2010, Fey had her own Phyllis-Diller-in-Playboy moment. One surprisingly smokin'-hot Tina Fey graced the cover of Esquire, vamping in red lipstick, stilettos, and handcuffs. It's hard not to look at the hard-partying themed spread--especially the cover image--without hearing a Tracy Morgan-style "Damn, Liz Lemon!" in your head. But Fey herself was quick to declaw any notion that the photos had captured the real, raw, "unleashed" Tina Fey. "The idea of the photo shoot is something like my wild night out. The irony being that I don't do that," she explained in the accompanying interview. "I got to get my kid into kindergarten." Almost every photo from the spread, too, features ­­Fey cheekily derailing the shoot's straight-faced, male-gaze sensuality--absentmindedly streaking lipstick across her cheek, for example, or falling into a laundry cart in the hallway of a swanky hotel.

Barreca says there's a line in the sand for women: On one side, there's too funny to be sexy, and on the other, there's too sexy to be funny. And trying to straddle that line, she says, doesn't often end well. For instance: If Fey had arched up against that laundry cart in full come-hither mode, or if Playboy had published those photos of Diller, she says, there would have been cognitive dissonance. "Women couldn't be attractive and smart, or attractive and funny," she says. "Attractive and anything else, really."

The onstage Phyllis Diller fans came to love in the 1960s wasn't just laughably unfortunate-looking, though--lest we forget, she was also lazy, rampantly irresponsible, clumsy, and as hopeless in the bedroom as she was in the kitchen. Diller told audiences she hated office Christmas parties because it was such a bother to look for a new job the next day; she professed to love going to the doctor because, as she put it, "Where else would a man look at me and say, 'Take off your clothes'?"

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Ashley Fetters is a former associate editor at The Atlantic.

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