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6 Iconic David Letterman Interviews

As the late-show host announces his retirement, we look back at six of his most memorable interviews

Joaquin Phoenix David Letterman

Joaquin Phoenix David Letterman

John Paul Filo/CBS

He was a former weatherman and a failed morning-show host who perfected a sort of snide, irreverent attitude towards showbiz types. After getting noticed by Johnny Carson and making a fan out of NBC bigwig Fred Silverman, however, David Letterman found himself taking his goofy antics to a 12:30am time slot — and thus, a late-night TV legend was born. When Letterman announced during the taping of his show today that he would definitely be retiring next year, he signalled the beginning of the end of a three-decade-plus career of entertaining people in the wee small hours. And while he was definitely the reigning King of Late-Night Smart-Assery, Letterman could also do wonders with a celebrity interview —the stranger or more shocking, the better.

David Letterman Announces He’s Retiring in 2015

In honor of The Late Show‘s host saying he was rounding the track for his last lap, we remember six of his most iconic interviews. From nearly taking a kick to enduring performance-art schtick, here’s a six-pack of Dave behind the desk, on his toes and at his best.

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Andy Kaufman vs Jerry Lawler (July 29th, 1982)

Only somewhat settled into their late-night perch, Letterman & co. decided to book an old friend: meta-stand-up Andy Kaufman, then deep into his pro-wrestler phase. The host had also invited on Kaufman's nemesis, Jerry "The King" Lawler, who injured the comedian during a match the previous spring. After a lot of mutual trash-talking, Lawler stood up and slapped Kaufman right out of his chair. The feud between the two men was later revealed to be a hoax — but neither Dave nor anyone in the audience (or folks watching at home) knew it was all a put-on. The sense of danger and anything-goes chaos was palpable, and the incident made headlines. Letterman and Late Night had arrived.

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Crispin Glover Kicks Off His First ‘Late Night’ Appearance (July 28, 1987)

You could tell things were going to get odd the moment The River's Edge star walked out wearing a wig, skintight pinstripe pants, platform shoes and a seriously nerdy pair of glasses; he appeared to be shouting something to somebody in the wings before turning, deer-in-the-headlights style, to face the audience. This infamous interview only got weirder once Glover and Letterman started "chatting," as the actor proceeded to read unflattering stories about himself from the L.A. Weekly aloud. ("Is this the first time you've seen a man die, Paul?" Letterman asked his bandleader.) Then Glover started challenging Letterman to an arm-wrestling match and proceed to unleash a karate kick that missed Dave's face by inches. "I have to check on the Top Ten list," the host said, and walked off. The interview had ended, but Glover's reputation as a volatile kook had officially begun.

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Madonna’s Less-Than-Holy Appearance (March 31st, 1994)

"She's sold over 80 million albums, starred in countless films, and slept with some of the biggest names in the entertainment industry," joked Letterman before his guest sat down; apparently, Madonna felt the need to one-up Dave in the shock department after such an auspicious introduction. After ribbing the host about his "obsession" with her sex life, the pop star then proceeds to smoke a cigar and say the F-word a record 14 times. Controversy and FCC handwringing ensued, as did high ratings for Dave's show (now at CBS). It was neither the first time she'd sat across from Letterman's desk nor the last, but it's still the most memorable of her apperances.

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Warren Zevon’s Long Goodbye (October 30, 2002)

He was the only guest scheduled for the entire show that night, which viewers might have chalked up to Letterman being a legendary superfan of the singer-songwriter. But it was apparent once Zevon announced that he had terminal lung cancer, however, that it became apparent that Dave wanted to give the musician a nice, long victory lap. Zevon would crack wise, play several numbers — including the host's favorite, "Roland the Headless Thompson Gunner" — and advise everyone to "enjoy every sandwich" before the hour was up; he'd also bring out a tender side of Letterman that people weren't used to seeing. It was the final appearance Zevon would make on the show; he'd pass away 11 months later.

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Oprah and Dave Bury the Hatchet (December 2nd, 2005)

It was a "feud" that lasted 16 years — but after Letterman virtually pleaded for the daytime talk-show host/lifestyle guru to appear on The Late Show for months and months, Oprah Winfrey finally gave in. Entering to a timpani fanfare and copious applause, Winfrey embraced the host and the two immediately made up for lost time. The two talked about kids' books and Dave's "Uma, Oprah" Oscar moment while making nice with each other; for someone who'd made his bones by being cynical and sarcastic, it was sweet to see Letterman so conciliatory.

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Joaquin Phoenix: Professional Beardo (February 11th, 2009)

"You look different than I remember you," said Letterman to the Oscar-nominated star, and it was safe to say he was speaking for everyone who'd tuned in to see Phoenix sporting a hermit's beard, sunglasses and shabby black suit. After mumbling about retiring from acting so he can pursue a hip-hop career and thouroughly alienating everyone — including the host — Letterman cracks "Well, I'm sorry you couldn't be here tonight, Joaquin." Now, we know that whole interview was part of a performance art-cum-film project that Phoenix was working on ("I'm Still Here"), and the star would eventually return to the show a little over a year later to apologize. At the time, however, it was simply one of those can't-watch-can't-look-away car-wreck appearances that had become hallmark of The Late Show.