Entertainment David Letterman retiring: His most memorable moments By amNY.com Updated April 3, 2014 6:14 PM Print Share fbShare Tweet Email 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 Photo Credit: YouTube 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. Watch the clip Crispin Glover: 1987 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. Watch the clip Bill O'Reilly: 2009 Photo Credit: YouTube 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. Watch the clip Joaquin Phoenix: 2009 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. Watch the clip Jerry Lawler and Andy Kaufman: 1982 Photo Credit: YouTube 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. Watch the clip Jerry Garcia and Bob Weir: 1982 Photo Credit: YouTube 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.) Watch the clip Paris Hilton: 2007 Photo Credit: YouTube 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. Watch the clip 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? Watch the clip Courtney Love: 2004 Photo Credit: YouTube 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. Watch the clip Bryant Gumbel: 1985 Photo Credit: YouTube Letterman had everyone laughing with his bullhorn prank on Bryant Gumbel during the taping of "The Today Show." Watch the clip By amNY.com Share on Facebook Share on Twitter Comments We're revamping our Comments section. Learn more and share your input.