Late-night talk shows are a part of the American cultural landscape. They have been around now, in one way or another, for close to 70 years.

With so many different shows, so many great and iconic hosts, and so much time on the air, you’d certainly expect these shows to produce an enormous wealth of unforgettable moments.

And they most certainly have. Here are some of the most hilarious, shocking, disturbing, and otherwise memorable moments in the history of late-night TV.

Madonna Drops the F-Bomb

Madonna’s entire career is a living embodiment of the idea that there’s no such thing as bad publicity. From the very beginning, she has made a name for herself by pushing boundaries, turning heads, and shocking people.


And when she appeared on Late Night With David Letterman, she certainly continued to do that. Madonna holds the record for the most censored late-night interview of all time, blurting out the f-word a total of 14 times. Plus, the interview was peppered with all sorts of barbs and innuendo, so the atmosphere between her and David Letterman was extremely tense.

Drew Barrymore Flashes David Letterman

Drew Barrymore comes from a famous acting family. She first came to national attention for her role in E.T., but as the 1990s began to dawn and Barrymore entered into adulthood, she began taking on the image of a wild and seductive party girl.


David Letterman learned that first hand when she appeared on his show and sat down for an interview with him in 1995. The interview proceeded normally at first, with Letterman making the playful and humorous banter that he was so well-known for. Suddenly, though, Barrymore got the idea to stand on Letterman’s desk and perform a seductive dance. For one brief moment, she turned her back to the crowd, lifted her shirt, and flashed Letterman.

The look on his face was priceless.

Three Cheers for Cheers

When the show Cheers finally came to an end in 1993, after 11 years on the air, Jay Leno decided to invite the cast on The Tonight Show and interview them. Ted Danson, Woody Harrelson, Kelsey Grammer, George Wendt, Rhea Perlman, and others all appeared. For added effect, the whole segment was filmed from the famous Cheers bar in Boston.


What Leno didn’t know, however, was that the cast members had started drinking before the interview had even begun. By the time Leno had begun talking to them, and everyone was on live TV, the entire cast was completely hammered. Millions of people saw all of these actors completely drunk out of their minds.