It was thirty years ago today that Madonna made an infamous appearance on Late Night with David Letterman. 

The interview was described as a train-wreck for both the music star and the late-night talk show host, and critics of singer decried she’d “reached a new low.”

Madonna had appeared on Letterman before, but the previous year he’d quit NBC and set up a new show at rival broadcaster CBS. This was her first appearance on his new show Late Night with David Letterman.

She’d faced a lot of criticism in the USA in the proceeding years for the overt sexuality presented in her Sex book, the accompanying album Erotica, and her role in the erotic thriller Body of Evidence.

Madonna’s appearance on the show came at an odd time. Having finished a world tour in Tokyo the previous December, Madonna’s only musical release had been the sedate track I’ll Remember which appeared on the soundtrack to the film With Honors, directed by friend Alek Keshishian. Her next album Betime Stories was still six months away. Madonna went on to Letterman with no new work to chat about.

In the interview the singer presented the host with a pair of her undergarments and asked Letterman if he wanted to sniff them. He said he’d save them for later.

She managed to drop the F-bomb 14 times during the chat, and a conversation about her dating life left audiences a gasp. The studio audience jeered the singer and told her to get off, but she refused to leave the set. After a commercial break Madonna was no longer there.

It was later claimed that Letterman’s team were fully aware that Madonna was going on the show to make a comment about television censorship, but the host had not handled the exchange well, and Madonna had gotten annoyed at his questions about her personal life.

In the years that followed Madonna appeared on Letterman’s show several times, but it would be six years before they had another sit-down chat.

Six months later Madonna was finding new success with her Bedtimes Stories album, but she returned with a much more conservative image, and ballad heavy R&B sound.

Website Late Nighter has assembled an oral history from many of the people who worked on the show, revealling exactly what went on behind the scenes. 

OIP Staff