David Letterman's ratings when through the roof when this pop star insulted him

David Letterman just did what he wanted. There are tons of examples of the talk show host stepping over the line or making fun of his guests, but none of his awkward interactions topped a particular episode of Late Show from 1994.

Letterman met his match in the guise of a pop star. He tried to make demeaning remarks about the guest's personal life, and urged her to kiss a member of the audience. The pop star, however, fired back and proceeded to call him a "sick f**k" in return. Who was the pop star? None other than the queen of controversy herself, Madonna.

Letterman and Madonna clashed back in 1994

Letterman sealed his fate before Madonna even walked out. He mentioned that the pop star had "slept with some of the biggest names in the entertainment industry," which even managed to get a shocked response from Letterman's sidekick, Paul Shaffer.

The disdain was palpable. Madonna claimed that she had smoke marijuana prior to going on the show, and Letterman repeatedly mocked her about her sexual habits. He asked if she wanted to kiss a random man in the audience, and when she balked at the notion, the host mockingly congrajulated her for not succumbing to peer pressure.

Madonna proceeded to call Letterman "twisted" and "suck" amidst a tangent that include 14 f-bombs and various sexual innuendos. In the biography, Madonna: Like an Icon, author Lucy O'Brien claimed that Madonna refused to leave the set. She was booed by the Late Show audience, and then ordered to leave the set by producers.

Madonna was ordered to leave the Late Show set

Letterman tried to make light of the situation when the show came back from commercial, but even he acknowledged that things had spun out of control. "Oh, I see we've been canceled," he quipped. "There is no show tomorrow night."

Not only was there a show the next night, but the disastrous interview became a massive story. The episode featuring Madonna became one of the highest rated of Letterman's entire late night career. It had a less positive impact on the pop singer, with many describing the interview as one of her lowest moments.

Both Letterman and Madonna went on to dominate 90s pop culture and beyond, though. The latter even returned to Letterman's shows over the years, to prove there was no hard feelings.