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“I’ve had a great run.”

Last week, Paul Shaffer, the musical director for (and sidekick of) David Letterman spoke about their 33-year history on the air together, on NBC (1982-93) and CBS (1993-2015). Canada’s Schaffer picked an appearance by James Brown in 1982 as his favourite musical moment, while host Letterman brought up a 1984 drop-by appearance by Bob Dylan. On May 20, Letterman and Shaffer retire. With that in mind, here are the Top 10 best musical moments from Late Show with David Letterman and its predecessor Late Night with David Letterman.

No. 10 It got weird in the eighties, and nobody can afford to remember it all. But there was the night in 1984 that Latino punk band The Plugz backed Bob Dylan for three songs, including Jokerman.

No. 9 Paul Simon and Art Garfunkel harmonized on The Boxer and America in 2003, but Garfunkel had eased our mind even more with his epic solo version of Bridge Over Trouble Water a decade earlier.

No. 8 More than 4 million YouTube hits can’t be wrong. With its Seasons (Waiting On You), in 2014 the Baltimore synth-pop band Future Islands wowed the Internet and thrilled an ecstatic Letterman too: “I’ll take all of that you got! That was wonderful!”

No. 7 Earlier this year, the Canadian funnyman Martin Short appeared for the 42nd time as a Letterman guest, swinging from the ceiling. “Talk about deflated balls,” he crooned on Fly Me Through This Room (a parody of the Sinatra-famous Fly Me to the Moon), “this harness is way too small.”

No. 6 “If you like gap-toothed men in double-breasted suits, he’s No. 1 on your top-ten list.” Last week, comedian Adam Sandler strummed a hilarious (but heartfelt and commendable) ode to the dentally unique Letterman, whose name Sandler rhymed with “no better man.”

No. 5 Late Show with David Letterman on CBS was taped at New York’s Ed Sullivan Theater, the same venue in which the Beatles made their American television debut on Feb. 9, 1964. In 2009, Paul McCartney was back where he once belonged, performing the Beatles’ classic Get Back atop the theatre’s marque.

No. 4 The World’s Most Dangerous Band was never more dangerous on the night in 1982 when James Brown got his groove on with Sex Machine, There Was a Time and I Got the Feelin’. Brown felt good; we all felt good.

No. 3 In 1987, Cher put her little hand in Sonny Bono’s during I Got You, Babe. The famously divorced couple crooned amicably and sweetly, thus creating one of pop music’s most touching televised reunions.

No. 2 In October, 2002, the Letterman friend and Werewolves of London singer Warren Zevon sat in with the band for a week, during which Letterman devoted an entire show to the rocker who had recently been diagnosed with cancer. Roland The Headless Thompson Gunner – Letterman begged him to play it – was the final song Zevon ever sang in public; he died 11 months later.

No. 1 On the night in 2000 when David Letterman returned after heart surgery, the musical guest was Foo Fighters. “My favourite band playing my favourite song,” the appreciative host said, before Dave Grohl and company roared through Everlong. “If everything could ever feel this real forever,” Grohl sang. “You gotta promise not to stop when I say when.”

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