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Flashback: Bob Dylan Sings With Country Leading Ladies on ‘Letterman’

Legend’s backing choir for the show’s 10th anniversary special included Emmylou Harris, Rosanne Cash and Nanci Griffith

Bob Dylan took the Ed Sullivan Theater stage as David Letterman’s second-to-last musical guest Tuesday night, returning to the Late Show nearly two decades since playing “Forever Young” in 1993. But it was his appearance the year prior on the Titanic that was Late Night With David Letterman’s 10th anniversary show that stands out not only for its all-star choir — Rosanne Cash, Nanci Griffith, Emmylou Harris, Mavis Staples and Michelle Shocked — but for the foreboding undertone to all that celebrating. Dylan hates manufactured pomp and circumstance almost as much as Letterman, but somehow the two came together on this special that aired only months before the host was denied The Tonight Show crown. But when they reunited Tuesday night, they docked the ship instead of watching it sink.

Letterman never got bullied into doing another one of those retrospective anniversary shows again, but at least for his 10-year, he pulled out all his favorites: Harris, Staples, Carole King on piano and, of course, Dylan, who personifies the art of the singer-songwriter that Letterman holds so dear. So how was the performance itself, a version of “Like a Rolling Stone” with a heavy dose of Paul Shaffer steroids? A little awkward, with the girl choir dancing strangely to the side like a Richard Marx video in pantsuits; but Dylan and Harris hadn’t officially sung together since she provided background vocals for Desire, so that pairing, along with Dylan’s long-documented crush on Staples, made the whole thing thrilling for the geekier fan (Letterman himself, namely).

Dylan’s arguably lackluster performance is commonly credited to a rumored disagreement with Shaffer prior to the special airing: Letterman reportedly requested “Stuck Inside of Mobile With the Memphis Blues Again,” while Shaffer wanted “One of Us Must Know.” But Dylan? He just wanted to play with his small band, not a celebrity-filled entourage. “I don’t need this band to play my music. Me, I got four pieces. That’s all I need,” he said. He got what he wanted at that 1994 appearance, playing a beautiful “Forever Young” embellished by ace steel guitar courtesy of Bucky Baxter.

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