30 most shocking moments in late night history
By Jeremy Dick
![NEW YORK - FEBRUARY 11: Actor Joaquin Phoenix, waves to the audience during his interview with Late Show host David Letterman during the Late Show with David Letterman Wednesday Feb. 11, 2008 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo by John Paul Filo/CBS via Getty Images) NEW YORK - FEBRUARY 11: Actor Joaquin Phoenix, waves to the audience during his interview with Late Show host David Letterman during the Late Show with David Letterman Wednesday Feb. 11, 2008 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo by John Paul Filo/CBS via Getty Images)](https://images2.minutemediacdn.com/image/upload/c_fill,w_720,ar_16:9,f_auto,q_auto,g_auto/shape/cover/sport/8ed16452841e9fc699b8f9cd5bde831b6b6e2f076586a02c07d87b2cd15bed0d.jpg)
4. Drew Barrymore flashes David Letterman for his birthday
E.T. child star Drew Barrymore had grown up by the time 1995 rolled around, having appeared nude in the first issue of Playboy of the year. Perhaps baring it all had made Barrymore become a little too comfortable with her body, to the extent of flashing a talk show host during his own show. As you can guess, that’s precisely what happened.
Letterman was lucky enough to invite Barrymore onto the show which would take place on his birthday, as the actress had planned a special “gift” for him. She would do a little dance on his desk before flashing him, with her back to the camera, giving him an up close and personal view of her body. Letterman was understandably shocked when it happened, but told her that he couldn’t thank her enough for doing it.
Barrymore would keep her clothes on as she matured, but the fun chemistry she developed that day with Letterman would see her brought back as a return guest many times. To this day, it remains one of the most shocking moments ever seen on late night TV, although it occurred so long ago that many of Barrymore’s younger fans might not know about it.
Next: 3. Conan trolls the network that screwed him