David Letterman's 5 Best Late Night Music Moments

David Letterman
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David Letterman is seen during a taping of the "Late Show with David Letterman" on Wednesday, April 2, 2014, in New York.

"What this means now, is that Paul and I can be married." There goes David Letterman, cracking wise about his longtime musical counterpart Paul Shaffer during a monologue Thursday announcing he'll retire next year. The longtime host, who launched NBC's "Late Night" in 1982 and CBS' "Late Show" in 1993, informed the audience at a taping today (April 3), the news being broken by R.E.M.'s Mike Mills in a tweet.

David Letterman's Retirement Scooped by R.E.M. Alum Mike Mills

In his 30-plus years at the helm of late night shows, Letterman has played host to a score of musicians, both as special and musical guests. From overseeing the Beatles' 30th anniversary of appearing on "The Ed Sullivan Show" to encountering Joaquin Phoenix's ill-fated rap career, here are five of the host's best music moments.

1) The Beatles' 30th Anniversary on "The Ed Sullivan Show"

The stage on which Letterman hosted "Late Show" originally housed the classic Ed Sullivan-led variety show, so it was only fitting that the celebration of the Beatles' performance on the show 30 years earlier would fall to Letterman and his crew. In commemoration? Naturally, "Top 10 Signs the Beatles May Be Here Tonight."

2) Madonna Drops 14 F-Bombs

Madonna isn't exactly known for her profanity, but when she unleashed a tirade of 14 f-bombs on Letterman's show in 1994, it bested even the dirtiest of potty mouths for the most censored episode in American talk show history. The episode was a ratings hit, apparently spurned on by the producers themselves, who the singer later said told her to curse as much as she did.

3) Warren Zevon Visits Letterman One Last Time

Warren Zevon was dying when he came to "Late Show" in October 2002, having contracted a form of lung cancer. To commemorate the singer's illustrious career, Letterman devoted an entire show to Zevon and Zevon only. Along the way, Zevon performed multiple times while giving the talk show host one of his final interviews and public moments before succumbing to cancer the next year.

4) Courtney Love Attempts to Flash Dave

In 1995, Drew Barrymore famously flashed her breasts at Letterman, certainly denoting one of the show's more memorable moments in its history. Nearly 10 years later, Hole frontwoman Courtney Love did the same thing, teasing it in a will-she, won't-she manner before finally jumping atop his desk and lifting up her shirt. What followed was a decidedly strange interview, Love seemingly barely coherent to interview. 

5) Joaquin Phoenix Visits Letterman to Pimp His "Rap Career"

We didn't know it at the time, but Joaquin Phoenix's brief foray into rap was actually an acting piece for his new mockumentary "I'm Still Here." When he actually appeared on the show to promote one of his new films at the time, Phoenix donned sunglasses and a long beard, a far cry from the actor many had come to know. His behavior was highly erratic, chomping on gum and seemingly unable to understand many of the questions posed. "Joaquin, I'm sorry you couldn't be here tonight," Letterman deadpanned at the end in one of his best lines on the show.