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10 Best Music Moments on 'Late Show with David Letterman'

The late night host is retiring after more than three decades, but that doesn't mean his legacy—and the legacy of his musical guests—won't live on. Check out our favorites here!

1 / 10

Le1f (2014)

Le1f's Letterman set wasn't only the rising hip hop star's television debut—it was the first time an openly gay rapper performed on a network late-night program. Donning a skort, he took the stage with two male dancers. Letterman didn't make mention of the rapper's sexuality, letting his high energy gig speak for itself.

2 / 10

Madonna (1994)

Not a performance, but Madonna did turn heads when she dropped a total of 14 f-bombs during this early '90s interview. To this day, the episode is still the most-censored American talk show, reaching record ratings. It was later revealed that the producers of the show told Madge to curse as much as she did, but for an unknowing audience, it came as quite the surprise.

3 / 10

R.E.M. (1983)

A young R.E.M. made their television debut on Dave's Late Show in 1983. The band was visibly nervous, and a usually charismatic Michael Stipe refused to talk.

Coincidentally, R.E.M.'s Mike Mills announced the host's retirement before the press got to it. Everything comes full circle?

4 / 10

Bruce Springsteen (1993)

Springsteen was the last guest to play Letterman when the host left NBC. The show—and the Boss' set—went into overtime, delaying the evening news. Punk!

5 / 10

Courtney Love (2004)

Ten years after Drew Barrymore famously flashed her breasts at the Late Night host, Courtney Love did the same. The grunge icon teased Letterman before jumping on his deck and exposing herself in this pretty NSFW clip.

6 / 10

James Brown (1982)

James Brown was one of the best performers of all time. James Brown's set on Letterman was one of the best televised performances of all time. Don't believe me? Click above.

7 / 10

Weezer (1995)

Frontman Rivers Cuomo was born with his left leg 1.75 inches shorter than his right. As a result, the pop-punk songwriter has to undergo surgery and routinely stretch. Cuomo rocked a brace for many years, which is visible in this 1995 Letterman performance. Pinkerton, and all its melancholy, makes a little more sense now.

8 / 10

Miles Davis (1987)

Miles Davis brought his brand of slowed-down cool to Letterman's stage, proving that quality live music doesn't always have to be rockin'.

9 / 10

Ted Nugent (1982)

Letterman and Ted Nugent duet on "The Christmas Song" in this Bing Crosby/David Bowie parody. 

10 / 10

Future Islands (2014)

Baltimore synth-pop band Future Islands are known for their live shows for one distinct reason: frontman Sam Herring's dance moves. Maintaining a hunched position, Herring's fluid dance moves are inimitable, causing Letterman to exclaim, "I'll take all of that you got! That was wonderful!"

The recent clip already has more YouTube plays than any other musical guest in the show's history. 

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