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David Letterman’s Top 10 Musical Moments

From Sonny and Cher’s reunion to Future Islands’ freakout, the most memorable performances during Dave’s 33 years in late night

David Letterman

David Letterman onstage with the Foo Fighters and Zac Brown on 'Late Show with David Letterman,' Monday Oct. 13th, 2014.

Jeffrey R. Staab/CBS

When David Letterman permanently signs off the airwaves later this month, it won’t just be the end of one of the greatest comedy institutions in TV history — it’ll also close out an amazing showcase for musical talent. Nearly every episode of NBC’s Late Night With David Letterman and CBS’s Late Show With David Letterman had a musical guest, and it was the place where many Americans first saw everyone from R.E.M. and Weezer to Future Islands. We’ve put together 10 of the greatest musical moments from the shows’ history, and though the list is by no means complete — we could easily have gone to 100 — these are the performances we keep returning to over and over again. 

David Letterman

Warren Zevon – ‘Roland The Headless Thompson Gunner’ (2002)

Warren Zevon's appearance in October of 2002 was a gut-wrenching experience, as the longtime friend of the show had recently been diagnosed with an incurable form of cancer. Dave devoted the entire hour to the singer/songwriter, who famously said that the experience taught him to "enjoy every sandwich" during the interview segment. At the host's urging (Dave later claimed that he "begged" the musician to play it), Zevon closed out the night with his 1978 classic "Roland The Headless Thompson Gunner"; though the artist surprised doctors by living another 11 months, this was the final song he ever sang in public. 

Ben E. King

Paul McCartney – ‘Get Back’ (2009)

No matter how many legendary performances took place on the Ed Sullivan Theater stage during during the Late Show's run, nothing will ever top what took place there on February 9th, 1964 when the Beatles made their American television debut. That moment changed the world forever — so when Paul McCartney came back in 2009, he decided he didn't want to return to the same stage. Instead, he set up on the famous marquee of the theater and, in a recreation of the Beatles' last public performance in 1969 on the rooftop of Apple Records, hr put on a free show for the lucky crowd gathered on the street. (Here's Macca's rendition of "Get Back.")  

Ben E. King

Future Islands – ‘Seasons (Waiting On You)’ (2014)

These days, bands don’t have huge breakthrough on moments on television like they did in the pre-Internet era; there’s just so many ways for people to experience new music now. But occasionally a TV performance is so electrifying that it creates a viral sensation, and that’s exactly what happened when the synthpop band Future Islands went on Letterman. Frontman Samuel T. Herring poured so much passion and energy into his vocal delivery (and unique dance moves) that nobody could possibly ignore it. “How about that!” Letterman said. “I’ll take all of that you got. That was wonderful!” The world agreed — nearly four million views on YouTube, the appearance turned out to be a career-defining moment for the band. 

David Letterman

Darlene Love – ‘Christmas (Baby Please Come Home)’ (1986 – 2014)

Darlene Love is known for many different things. Some remember her as one of the main voices in Phil Spector’s Wall of Sound, singing “He’s a Rebel,” “Today I Met The Boy I’m Gonna Marry,” “Wait Til’ My Bobby Gets Home” and many, many others. Others will recall that she’s Danny Glover’s wife in the four Lethal Weapon movies. But to Letterman fans, she’ll always be that amazing singer that came on every December and belted out “Christmas (Baby Please Come Home).” It was an annual tradition from 1986 to last year, when she graced us with one last rendition. Here’s a compilation of her singing the song numerous times throughout the years; the holiday season will seem quite lonely without it.