Why Fans Will Never Forget Madonna's Appearance On David Letterman

When you think of David Letterman and Madonna, you think unique — and that might be the only thing the two stars have in common. Letterman is known for his wry sense of humor and hosting two successful late-night talk shows over the course of three decades, while Madonna is known for her music, dancing, and daring takes on fashion.

Letterman was the host of "Late Night With David Letterman" on NBC from 1982 to 1993, where he was known for his always-timely top 10 lists. He later brought his act to CBS with "The Late Show With David Letterman" from 1993 to 2015 (via IMDb). Meanwhile, Madonna is known as "The Material Girl," often called that due to one of her first hit songs. She also became known for her racy videos with decidedly sexual undertones (via Biography). 

So, when Madonna was a featured guest on Letterman's CBS show in 1994, it was an appearance that the host — and the audience — would remember for years to come.

Madonna had a very special request of David Letterman

"The Late Show With David Letterman" hadn't been on the air for very long when Madonna stopped by as a guest one day in 1994 — and she didn't hold back. The interview quickly went off the rails when Madonna uttered the "F" word no fewer than 13 times as she answered Letterman's questions and went off on her own tangents (via Far Out). 

When Madonna walked out clad in all black, with slicked-back black hair, she immediately told Letterman that she was only there because there wasn't a New York Knicks game that night. Oddly enough, that prompted Letterman to tell Madonna to go kiss a guy in the audience — because why not? Madonna then had to ask why Letterman was so obsessed with her sex life. As the conversation went on, Madonna also called Letterman a "sick f***."

The banter continued like this for the next several minutes and, finally, Madonna did one more thing nobody expected — but perhaps shouldn't have been so surprising since this is Madonna, after all. The singer, who was smoking a cigar at one point, handed Letterman her underwear and asked him to smell them. While he hemmed and hawed and said no, she kept bringing it up as the two dropped sexual innuendos throughout the conversation. He does his best to cut to a commercial, but Madonna doesn't want to. She said that she just wanted the chat to go on and on, to which Letterman deadpanned, "I feel like it already has."