Drew Barrymore Flashed David Letterman As A Memorable Birthday Gift

Drew Barrymore was a sprightly 20-year-old, but she recalls flashing David Letterman in 1995. As a guest on his show, she hatched the idea to give him an unforgettable birthday gift. She didn’t know how it would end up, but she flashed her boobs to a stunned Letterman, who couldn’t thank her enough in the end, citing an ET Online report.

Drew, 40, appeared on the Late Show on the host’s 48th birthday. In a purely spontaneous moment, Barrymore jumps onto Letterman’s desk and began dancing provocatively as if she were doing a striptease. Then, the magic happens: she flashes David, and the rest is history, as she recalls.

“He’s always been known as the person who had no problem letting the audience know he was not down with what the guest was doing. It was scary.”

Letterman was left speechless after Drew’s boob-flash. “I can’t thank you enough for that,” he said to Barrymore. And after that Kodak moment, the two would go on to remain close over the years, the Grey Gardens actress told Entertainment Weekly in an interview.

“From that infamous show, we developed a really fun chemistry. Then I just looked forward to going back. There’s an energy to his show. The more you tried to charm him, the less he wanted it. He either liked you or he didn’t. When you usually go on a talk show it’s very buddy-buddy. But with him you have to work for it. But not too hard, because he won’t like that!”

Drew is not the only guest who’s flashed Letterman. Ahead of David signing off, Ellen DeGeneres recalled “stripping” for the veteran late night host. While helping him with his “Top 10 Things That Have Been on Ellen DeGeneres’ Mind Lately” list, Ellen flashed the audience by stripping off her pants and top that were pixelated for the viewing audience.

Well, unlike Drew’s flashing moment to Letterman, Ellen’s parting gift was a mash-up. Thanks to her clever use of the green-screen, she appeared to go completely nude. Had that been real, it would have been a moment Letterman would have never forgotten, right?

The longtime funnyman retired from his post on the late night show after being at the helm for 33 years. Arguably, Letterman is still thinking about that night Drew flashed him.

[Photo by David Buchan/Getty Images]