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

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.

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.

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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'?"

But Diller, who was married three times and had five kids, clearly wasn't quite as much of a slouch in the love and relationships department as she made herself out to be. She also held a degree from Bluffton College, and she worked steadily and successfully from the time she was 35 until as recently as August of last year, when she appeared on her friend (and disciple) Roseanne Barr's reality show.

Fey, similarly, is married with two daughters; she's the face of Garnier hair color treatments, and lives in a posh apartment on Manhattan's Upper West Side. But many of the running gags on 30 Rock revolve around Liz Lemon's sloppiness and chronic singledom. So why are we laughing at Diller and Fey for their shabbiness, their sofa dependence, and their chronically sad love lives? Why do these well-loved, impressively accomplished women invent incompetence to fuel their comedy?

Barreca, a humorist herself, puts it simply. "Women lead with their vulnerabilities," she says. "This is how we get men and other women to like us."

Humor, Barreca explains, is in itself an act of power and aggression; audiences are known to be intimidated by comedians, especially at live venues. (That's why nobody sits in the front row, she says.) "When women in are in comedy, there still needs to be a certain mitigating factor for the ferocity that goes with any kind of effective humor," Barreca says. "So if we show someone our neck, rather than our squared shoulders, we'll be more appreciated--and they'll permit us into their company."

Robert Lynch, a cultural anthropologist from Rutgers University and a part-time stand-up, agrees: "Maybe women have to go overboard with the self-deprecation because comedy can be an alpha thing," he says--the alpha being the class clown, the attention-grabber, the presence dominating the room. "Women alphas in general tend to be disliked. They can sometimes be distrusted, I think. And they're not sought after."

"The female stand-ups I know," he admits, "they don't get a lot of dates out of it."

That can be traced back to evolution, according to Lynch. Citing a 2005 study that aimed to distill how humor was prioritized in the selection of friends and lovers, Lynch explains that men and women both look for a "sense of humor" in companions--but define that phrase in vastly different ways. "What men mean by 'a sense of humor' is that they want someone who laughs at their jokes," Lynch explains, "and what women want is [someone who's] funny."

And thus, "Self-deprecation probably does work better for women," Lynch says--but he points out that guys like Ricky Gervais employ it, too, and just as effectively. "Gervais jokes about what an elitist asshole he is, because he realizes you've got to be an everyman, not an elitist [jerk]," Lynch says. "A big part of humor is rearranging hierarchies, and putting other people down." So comics of both genders, he says, often self-deprecate early in the routine to, one could say, come down to the audience's level.

And according to Barreca, that's why Diller's formula worked, and continues to work, so well. Already in a doubly threatening position as an uproariously funny woman as well as an attractive one, Barreca says, "She stooped to conquer."

Stooping to conquer wasn't a new tactic, of course. Rodney Dangerfield and Milton Berle had mastered ityears before Diller came along. But it was Diller who first turned that approach onto the notion of womanhood--and in so doing, she managed to disguise a distinctly highbrow point in distinctly lowbrow humor.

"She used herself as the target of her humor, yes," Barreca says. "But when you really listen to what she was talking about, she sort of systematically undermined the institutions associated with traditional femininity." Like the French feminist philosopher Simone de Beauvoir, Barreca says, Diller demonstrated that femininity is performative; or, in other words, that women are only as "feminine" in behavior as they decide to be."So Simone de Beauvoir and Phyllis Diller were absolutely on the same page," Barreca says with a laugh. "Straight trajectory."

The awkwardization of the self that Diller first perfected back in the 1960s and 1970s has grown to mainstay status in women's comedy as we know it today. From Julia Louis-Dreyfus's impetuousness, gawky dance moves, and all-consuming frizz (early on, at least) as Elaine Benes on Seinfeld to the countless public wedding-party embarrassments Kristen Wiig tackled with gusto as Bridesmaids' social train wreck, Annie; even Nora Ephron's self-effacing claim that she was the only White House intern during the Kennedy administration that JFK didn't bother to hit on: These are just a few of the notable examples of the successful, well-educated, ambitious--and yes, beautiful--comedy-devoted women who have taken a page out of Diller's masterful stooping-and-conquering book. It's a list that also includes Sandra Bullock, Amy Poehler, Judy Tenuta, Lisa Kudrow, and, of course, Diller's contemporary Joan Rivers.

And what of Tina Fey, the successor to Diller's underbragging throne? Fey might be the best example of all: As the creator and head writer of 30 Rock herself, Fey uses Liz as a dumbed-down avatar for herself. Liz is often the butt of the other characters' jokes on the series--for reasons ranging from her pitifully dormant love life to her hygiene habits. "You still have a good body!" one ditzy colleague reassures her. "How'd you dress before you were married?"

"I've never been married," Liz responds through a forced smile.

"Oh, really? I thought you had, like, three kids," the coworker replies. "Sometimes you have, like, food stains on your shirt. So I just figured, you know. Kids."

The brighter side to all this, of course, is that Phyllis Diller proved once and for all women in show business didn't have to be beautiful--or sweet, or well-dressed, or angelically pleasant--to be beloved. Though Diller herself was well-endowed in all the graces of womanhood, the immense popularity of her clumsy, outrageous onstage alter ego proved that it was OK to not be.