5 Sexist David Letterman Moments That Tainted His Long Late Night Legacy

As David Letterman prepares to say goodbye with his final episode of Late Show With David Letterman Wednesday night, many have begun looking back at the host's funniest and most memorable moments. While there's no question that Letterman pushed the boundaries further than other late-night hosts and his lack of fear over offending the audience or even guests was something to behold, that doesn't mean all of his jokes are to be revered. Although Letterman was normally on the right side of social progress, he has told his fair share of sexist jokes that unfortunately mar an otherwise bright and bold television legacy.

Letterman's sexism charges stem beyond his jokes and seemingly unfiltered quips. Some have accused the host of running a sexist working environment behind the scenes, a charge that was seemingly validated when Letterman himself admitted on air in 2009 to having extramarital affairs with several female staffers. In October 2009, the same month that Letterman made his confession, former Late Show writer Nell Scovell — one of the few female writers in the show's history — wrote a tell-all account for Vanity Fair, in which she describes her less-than-pleasant experience on his staff:

There’s a subset of sexual harassment called sexual favoritism that, according to the Equal Employment Opportunity Commission, can lead to a “hostile work environment,” often “creating an atmosphere that is demeaning to women.”And that pretty much sums up my experience at Late Night with David Letterman.

Although Letterman confessed to the affairs and apologized to his wife on air, he never spoke about Scovell's piece in 2009. Bustle has reached out for comment. These revelations paint a darker picture underneath all the on-air jokes and laughter. But at times, that darkness has even crept up to the surface. Here are five sexist Letterman' moments.

Whore Joke

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Letterman crossed the line again as recently as last month, when he silenced the audience with an unabashedly sexist joke. During the warmup portion of the taping, which is not aired, Letterman opened up questions to the audience and one member asked what advice the host would give to this year's graduates. Letterman said:

Treat a lady like a whore, and a whore like a lady.

What?? What does that have to do with transitioning from collegiate life to the working world? Absolutely nothing. Regardless, it's just awful, sexist advice. According to the New York Post, the audience was noticeably uncomfortable and one viewer called the advice "disrespectful to women."

Madonna

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In 1994, before Madonna's appearance on the talk show, Letterman gave her an introduction that made a vulgar joke about her sexual history.

Our first guest tonight is one of the biggest stars in the world. In the past 10 years, she has sold over 80 million albums, starred in countless films and slept with some of the biggest names in the entertainment industry.

Understandably, she was not amused, and being the badass that she is, Madonna proceeded to drop the f–bomb on his live program 14 times, including when she called him a "sick fuck."

Lady Gaga

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When Lady Gaga visited the show in 2011, Letterman — just like he did with Madonna — became fixated with something other than the real reason she was on the show, which was to promote her album Born This Way. Letterman began by asking about her outfit, which was a black rubber bra, black jacket, black boy shorts, and knee-high lace-up boots with a black mask. After she told him what she was wearing, Letterman said:

You and I are very different in that way. I have never thought to myself, "I’m just going to wear my underpants."

Focusing so much inane attention on her outfit seemed really out of touch — it was as if he'd never seen Lady Gaga before. If there's one thing the world has learned about Gaga, it's that she wears whatever she wants.

Sarah Palin

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Letterman acknowledged that he had crossed a line when he made an inappropriate sexual joke about Sarah Palin's daughter, who he thought was 18-year-old Bristol but was in fact 14-year-old Willow. During his opening monologue, Letterman joked:

One awkward moment for Sarah Palin at the Yankee game, during the seventh inning, her daughter was knocked up by Alex Rodriguez.

Letterman later apologized on PBS's NewsHour:

I told a joke that was beyond flawed, and my intent is completely meaningless compared to the perception. ... I would like to apologize, especially to the two daughters involved, Bristol and Willow, and also to the governor and her family and everybody else who was outraged by the joke.

But Palin wanted him to apologize to women everywhere, saying on the Today show:

I would like to see him apologize to young women across the country for contributing to that kind of thread that is throughout our culture, that makes it sound like it is OK to talk about young girls in that way, where it's kind of OK, accepted and funny to talk about statutory rape.

Boner Joke

Of the many, many female celebrities Letterman has flirted with throughout his show's 22-year run, the host was excessively aggressive with Charlize Theron in 2008. After making a big fuss over how good she looks in her low-cut dress, the actress says that her birthday is coming up and asks if he's going to send her anything. Letterman responds, "I'm sending you something right now" (ew), to which Theron quickly retorts, "I didn't want that."

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