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David Letterman retiring: His most memorable moments

David Letterman is retiring from late night television in 2015 after 33 years as a host for both "The Late Show" and "Late Night." We take a look back at some of his most memorable on-screen moments.

Drew Barrymore: 1995

A fresh-faced but up-to-no-good Drew Barrymore offered to
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A fresh-faced but up-to-no-good Drew Barrymore offered to show Letterman a routine she learned at a "nude art performance dance place" (The Blue Angel Cabaret on Walker Street) and then proceeded to get up on his desk and flash him.
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Crispin Glover: 1987

The actor appeared entirely off his rocker, wearing
Photo Credit: YouTube

The actor appeared entirely off his rocker, wearing a wig and big platform shoes, and he challened Letterman to an arm wrestle and almost kicked him in the face before the host walked off set.
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Bill O'Reilly: 2009

Tell us how you really feel.
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Tell us how you really feel. "In my mind, I think of you as a goon," Letterman said to on-again-off-again nemesis O'Reilly, adding that he hopes his son doesn't turn out like him.
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Joaquin Phoenix: 2009

Awkward is the only word to describe Letterman's
Photo Credit: YouTube

Awkward is the only word to describe Letterman's Joaquin Phoenix encounter. The actor, who was on a break from acting to work on his "hip hop career," looked down, barely said a word and told Letterman he made him feel uncomfortable. That didn't stop Letterman from calling him out on his unruly beard and bizarre attempt at a career change.
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Jerry Lawler and Andy Kaufman: 1982

WWE Hall of Famer Jerry Lawler's contempt for
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WWE Hall of Famer Jerry Lawler's contempt for funnyman Andy Kaufman hit a boiling point right in front of Letterman's eyes, when Lawler whacked Kaufman right out of his chair. A profanity-filled rant ensued.
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Jerry Garcia and Bob Weir: 1982

In this famous interview, Letterman
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In this famous interview, Letterman "teaches" Bob Weir how to play guitar and asks him and "The Grateful Dead" band-mate Jerry Garcia for their favorite memories from the late 60s. (They admit they don't remember much.)
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Paris Hilton: 2007

After exchanging pleasantries, Letterman dove right into interrogating
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After exchanging pleasantries, Letterman dove right into interrogating Hilton about jail, right down to each meal she ate. Eventually, the interview became too much for the heiress, who appeared on the verge of tears.
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Madonna: 1994

Photo Credit: YouTube

"Our first guest tonight is one of the biggest stars in the world... 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," Letterman said of Madonna. Then he asked her to go kiss a guy in the audience. She responded by calling him a profane name and asking him to smell her underpants. Because really, what else would she do?
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Courtney Love: 2004

Courtney Love used
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Courtney Love used "mocking" Drew Barrymore's appearance as an excuse to take her clothes off for Letterman, but somehow it was much, much worse the second time around.
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Bryant Gumbel: 1985

Letterman had everyone laughing with his bullhorn prank
Photo Credit: YouTube

Letterman had everyone laughing with his bullhorn prank on Bryant Gumbel during the taping of "The Today Show."
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