tv-lookoutOn the day the king of late-night longevity announced his plans to retire, we thought we’d take a look back at some of David Letterman‘s most memorable moments. We’ll start with two unforgettable incidents from his NBC days and work our way up through the CBS era. First, we set the wayback machine to the first Reagan administration …

Andy Kaufman vs. the Wrestler, July 1982
The polarizing comic was known at the time for wrestling women and mouthed off until he finally got into the squared circle with a man. He took on pro grappler Jerry “The King” Lawler and lost, falling victim to a piledriver. A few months later, the two faced off on Late Night:

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Crispin Glover Gets His Kicks, July 1987
The actor who played George McFly in Back To The Future — but, notably, not in the sequels — came to Late Night presumably to plug his film The River’s Edge. Instead, a decidedly odd and/or out-of-it Crispin Glover decided to show off his “strength,” and hilarity ensued. But not for Letterman, who promptly walked off the stage:

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Madonna Tests the FCC’s Limits, March 1994
Letterman had been having fun at the singer’s expense for years, peppering his monologue with jokes about her sexual escapades. When Madonna was a guest on his show, she unleashed a flood of profanities that might have made Sam Kinison blush:

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Drew Flashes Dave, April 1995
The heir to Hollywood’s Barrymore throne was a wee lass of 20 when she decided to give Letterman a birthday present he’d never forget. She climbed up on his desk, danced a little and … well, Dave’s face says it all:

Dave Returns From Heart Surgery, February 2000
Just after the millennium turned, Letterman had a routine checkup that revealed a blocked artery, and he was rushed into quintuple bypass surgery. Five weeks later (!), he returned to Late Show to — of course — joke about it. And thank some people:

Dave Addresses 9/11, September 2001
About a week after terrorists attacked his city, Letterman was back on the air — and he had some emotional, unscripted and none-too-subtle words about that awful day and its aftermath:

Two Lads From Liverpool Reminisce at the Birthplace of American Beatlemania, February 2014
Letterman chats with Paul McCartney and Ringo Starr for a CBS special celebrating the 50th anniversary of the Beatles’ U.S. television debut on The Ed Sullivan Show — in the theater where Late Show has been taping for more than three decades: