30 most shocking late night scandals

17. Drew Barrymore flashes David Letterman in front of his desk

In the 1990s, people were just as on guard as ever about what could be shown on television. Nudity, obviously, was something that was not allowed at all. But even hinting at nudity was still enough to spawn some controversy. So much so that one particular instance of implied nudity is still being talked about over 20 years later. And it involves the famous actress Drew Barrymore.

During an appearance on The Late Show with David Letterman in 1995, guest Drew Barrymore may have been too excited. Because she was feeling a bit frisky, and perhaps because it was to celebrate Dave’s birthday, Drew gave the host quite the surprise. With her back to the audience, Barrymore would lift her shirt and flash Letterman, prompting the crowd to go nuts.

Letterman jokingly responded that he couldn’t thank her enough for doing that. Afterwards, the interview gets somewhat more normal, and Barrymore would make other guest appearances following this. But that moment when she would expose herself to Letterman has become infamous. During the exit videos which would come when Letterman was finally retiring from the show, the Barrymore flashing incident was commonly shown and referenced.