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."