One of the most notorious interviews in late night history took place on March 31, 1994 when Madonna paid a visit to The Late Show With David Letterman.

The appearance came at a bumpy time in the singer’s career. Though Madonna was still unquestionably one of the biggest stars on the planet, she’d had more recent misses than hits. Her 1992 album Erotica, became the first studio LP since her debut to not reach No. 1. It’s themes were overtly sexual – even by Madonna’s standards – and her coffee table book Sex, released around the same time, received harshly negative criticism. Her 1993 film Body of Evidence – which featured scenes of bondage and sadomasochism – didn’t make things any better. All of these factors converged when she visited Letterman, and Madonna was anything but toned down during the interview.

For starters, the singer gave Letterman her panties after walking onstage, then was disappointed when the host said he wouldn't smell them. After teasing that she was only on the show “because there wasn’t a Knicks game,” Madonna preceded to call Letterman a “sick fuck.” It was the first of 14 f-bombs that she’d drop during the interview.

“You realize this is being broadcast, don’t you?” Letterman responded, only for Madonna to giggle at the situation. The host tried to steer the conversation into tame territory, asking Madonna if she was interested in buying an NBA team or whether that was just an “untrue rumor.”

“Isn’t that an oxymoron, an ‘untrue rumor?’” Madonna responded, before adding, “Oxymoron, “Like funny David Letterman.”

The interview continued like this, with both sides verbally sparring in various ways. For most of the conversation, any question Letterman asked resulted in a penis joke.

“Oh come one!” Letterman proclaimed at one point, when Madonna somehow made a question about her nose ring once again sexual. “What am I, speaking Chinese here? Stop it!”

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The Material Girl went on to mention the many jokes Letterman had made at her expense over the years, a subject which brought on some uncomfortable silence. When the late night host tried to go to a commercial, Madonna did her best to stop him.

“I don’t think that we should ever cut to a commercial. Let’s just keep talking and film every second of it,” she declared. “Oh yeah, because if the rest of it is as fascinating as the first part of it, we’ve got something there,” Letterman wryly responded.

Things continued to devolve throughout the interview. Madonna asked Letterman if his hair was “a rug.” The host responded by pointing at her tight black hair and asking, “What is that, a swim cap?”

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Madonna claimed that Letterman had gone soft since becoming successful, insisting “you just kiss up to everybody on your show now.” Letterman cheekily offered to “suspend that behavior tonight” in response.

Barbs flew back and forth, and every time Letterman tried to get the conversation on track, Madonna would gleefully deliver some more profanity.

“This is American television, you can’t be talking like that,” he declared. “Why?” Madonna asked in response. “Well, because people don’t want that in their own homes at 11:30 at night,” the host insisted.

'Can't We Just Break the Rules?'

Adding further awkwardness to the scene, Letterman’s director, who seemingly was trying to get the interview wrapped early to end the chaos. At some points, the studio audience also seemed to turn again Madonna, tiring of her explicit display. One elderly couple in particular was shown on camera several times, looking shocked and dismayed by the singer’s foul mouth.

“Why can’t we just talk to each other? Why do we have to have all of this contrived bullshit? Fuck the tape, fuck the list, everything,” Madonna stated at one point. “Can’t we just break the rules?”

“No!” came a shout from a man in the audience, obviously fed up with what he’d seen.

Watch Madonna's Infamous Interview With David Letterman

After 20 uncomfortable minutes, Letterman was finally able to go to commercial. When the show returned from the break, Madonna was gone. “Ok, coming up in the next half hour, Mother Teressa is going to drop by,” Letterman quipped, garnering some of the night’s biggest laughs.

Outrage Over Madonna's Letterman Interview

Media outcry followed Madonna’s controversial appearance. The New York Post ran a headline that said “STUPID MADONNA TRICKS - Sex Star Goes Ape on Letterman.” Others called her “shocking,” “disgraceful” and “a very rich has-been.” “Her once-exhilarating bravado and impudence have curdled into a sullen, crude rebelliousness,” opined Entertainment Weekly.

In subsequent conversations, Letterman took shots at Madonna and her tirade of expletives. Of course, the host couldn’t ignore one fact – her episode was a ratings bonanza. Approximately 9 million people tuned in for the interview, one of the most-watched episodes in Late Show history.

Tension from Madonna's appearance lingered for months as the interview and subsequent feud became one of pop-culture's most talked about topics. That September, Letterman and Madonna appeared together at the MTV Video Music Awards, holding hands in a moment that seemingly buried the hatchet.

"And you thought we wouldn't last," the singer announced, feigning that she and Letterman were a couple. "I'll be in the car. Watch your language," the host responded, walking offstage to laughter and applause.

Watch Madonna With David Letterman at the 1994 MTV Video Music Awards

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