EW Staff
March 25, 2011 AT 04:00 AM EDT

The pop icon’s March 31, 1994, Late Show visit turned into a ribald bleepfest that stunned viewers — and Dave himself

DAVID LETTERMAN has famously sparred with many celebrities on his late-night talk show (see sidebar), but his most buzzed-about guest spot remains his 1994 sit-down with Madonna. The 20-minute interview’s saucy tone was set up with Letterman’s introduction of the pop diva: ”In the past 10 years, she has sold over 80 million albums, starred in countless films,” he said, with his trademark smirk, ”and slept with some of the biggest names in the entertainment industry.”

Madonna, black hair slicked back, emerged with guns blazing — asking Letterman, ”Why are you so obsessed with my sex life?” The segment then devolved into a profanity-laced, often uncomfortable back-and-forth that saw the singer drop the F-bomb 13 times, among other naughty words — all of which were bleeped for air. ”Why do we have to have all this contrived bulls — -?” she asked when Letterman attempted to go to a taped segment. The Material Girl also puffed on a cigar, refused to go to commercial break, and insisted that Letterman smell a pair of her panties.

The show instantly became the stuff of late-night legend, with everyone from Conan O’Brien to actor Charles Grodin to comedian Robin Williams weighing in (Williams described the encounter as ”a battle of wits with an unarmed woman”). The interview proved to be a ratings bonanza, with Late Show pulling in 9 million viewers. Madonna, though, defended her language as an attack on censorship. ”You can show a person getting blown up, and you can’t say ‘f — -‘?” she huffed to Spin in the fall of 1995. ”It’s such hypocrisy. The fact that everyone counted how many f — -s I said — how small-minded is that? The way he introduced me was derogatory, so my whole thing was, okay, if that’s how you want to play it, you cannot beat me at this game.”

Joaquin Phoenix (Feb. 11, 2009)

The Oscar nominee mumbled and fidgeted his way through the interview before sticking gum under Dave’s desk. He returned last September to explain it was all performance art.

Farrah Fawcett (June 5, 1997)

The late actress appeared incoherent, distracted, and downright loopy, but insisted she was just bantering.

Drew Barrymore (April 12, 1995)

Barrymore danced on Dave’s desk and gave him an impromptu birthday gift — a topless peep show (albeit with her back to the audience).

Crispin Glover (July 28, 1987)

Glover’s outfit — a crooked wig, bell-bottoms, and platforms — didn’t make much sense, and neither did the actor. He tried to arm-wrestle and kick Dave, prompting the host to walk off stage.

Cher (May 22, 1986)

Looking less than thrilled to be there, Cher admitted that she had rebuffed previous offers to go on the show because Dave was an ”a — hole.”

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