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When David Letterman signs off from the Ed Sullivan Theater one last time on May 20, he’ll be saying goodbye to decades of interviews with celebrities and “celebrities” alike. As a farewell to Late Show With David Letterman, we’ve sifted through his countless chats—from the CBS program as well as his old NBC show, Late Night—to revisit the most ridiculous, notorious, and memorably off-script appearances Letterman’s ever emceed.

Andy Kaufman, 1982

The comedian “feuded” with professional wrestler Jerry Lawler in the early ’80s, culminating in a furious debate over who was to blame for Kaufman ending up in a neck brace. Skip to 9:13 to see Lawler deliver a slap that leaves Kaufman on the floor and scurrying behind Letterman’s desk after the commercial break.

Cher, 1986

In her first appearance on the show, Cher called Letterman an “a–hole.” In her last appearance, she apologized—and then did it again.

Madonna, 1994

After Letterman introduced the pop star by saying, “In the past 10 years, she has sold over 80 million albums, starred in countless films, and slept with some of the biggest names in the entertainment industry,” Madonna retaliated with 14 f-bombs and enough sexual innuendos to make the interview one of the highest-rated TV programs of the year.

Drew Barrymore, 1995

In 1995, a young Drew Barrymore hopped onto Letterman’s desk and delivered the flash seen around the world. “It was scary,” Barrymore told EW about the moment. “I’m so glad that from the moment I went on—especially with my fun little dance number, which was completely spontaneous and not calculated in any way—he let the audience know that it was all okay.”

Farrah Fawcett, 1997

Fawcett went a little off-script—or rather, make that way off-script. In a rambling interview, she impersonated a New Yorker, defined the word “embankment,” and baffled Letterman, who would go on to refer to her appearance in several shows to come.

Michael Richards, 2006

This one’s tough to watch. Richards—Kramer to Seinfeld fans—appeared on the show via satellite after Jerry Seinfeld persuaded him to make an on-air apology for spewing the N-word at a West Hollywood comedy club. Instead of inspiring sympathy from the studio audience, however, his disjointed appeal—along with his use of the term “Afro-Americans”—welcomed laughter that only made his situation worse.

Paris Hilton, 2007

The socialite was a frequent Letterman guest, but when she returned to the show in 2007, she had just left a short stint in jail. Letterman pounced on that fact right away, asking her how it was. “That’s how you start?” an incredulous Shaffer responded.

Joaquin Phoenix, 2010

Where to start with this one? The actor-turned-rapper (and later turned actor again) went on Letterman to mumble responses behind a full beard and unnecessary sunglasses. Letterman eventually gave up trying to coax full-sentence responses out of Phoenix, and told the star, “We’re sorry you couldn’t be here tonight.” It’s plenty uncomfortable to watch—even knowing that the whole thing was just an act for Phoenix’s faux-docmentary I’m Still Here.

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Late Show With David Letterman

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