“It Was So Bizarre”: Revisiting the Bob Dylan Performance That Baffled David Letterman (And Everyone Else Watching)

Bob Dylan has built an entire career on his mysterious, elusive reputation, but one performance in particular proved especially baffling to David Letterman and the rest of the world watching. For those who don’t consider themselves to be big Dylan fans, the songwriter’s performance might not have raised any eyebrows.

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But if you know, you know. And back in 1992, Letterman knew…even if he couldn’t quite wrap his head around what his guest performer was saying into the mic.

Bob Dylan Performs Strange Rendition Of Iconic Hit On David Letterman

On January 18, 1992, Radio City Music Hall was abuzz with stars, crew, and audience members eagerly anticipating the 10th anniversary special of Late Show with David Letterman. The celebration featured a wide variety of Letterman’s former guests, including Bill Murray, Carole King, Mavis Staples, and Bob Dylan. In a December 2024 appearance on the Barbara Gaines Show, a YouTube series hosted by the former Late Show executive producer, Letterman recalled the, er, interesting performance choice Dylan made that night.

According to Letterman, he had finished listening to a podcast about the cultural and musical impact of Dylan’s iconic 1965 hit, “Like a Rolling Stone,” when he felt compelled to look up performances of Dylan singing the song on Letterman’s show. He stumbled upon the archival footage of his talk show’s anniversary celebration, pressed play, and tried to listen—try being the operative word here. “You would think, ‘Oh, I better have my hearing tested,’” Letterman said.

The problem wasn’t in the stage mix, instrumentation, or broadcast resolution. It was Dylan’s voice, or, perhaps more accurately, mumbles. The songwriter muttered through his iconic hit in an almost indiscernible fashion, which, of course, might be par for the course in some non-Dylan fans’ opinions. However, Letterman said Dylan’s choice was a deliberate act of rebellion over the show’s stage setup.

The Songwriter Exacted His Petty Revenge Live On The Air

Bob Dylan might have a knack for delivering loose, rubato vocal performances, but his rendition of “Like a Rolling Stone” on the 10th anniversary special of Late Show with David Letterman was exceptionally slurry. As Letterman recounted the memorable performance with his show’s former executive producer, Barbara Gaines, the long-time television personality revealed that Dylan’s artistic choice was actually a form of petty, on-air rebellion.

“As Paul [Shaffer, Letterman’s band leader and long-time sidekick] tells it, Bob agreed to be on the show but did not realize he would be accompanied by others,” Letterman explained. “Bob was under the impression it would be Bob and his guitar. I think this was Bob’s little way of having fun. I had forgotten it was odd. But boy, is it odd, especially after you’ve had half an hour of a guy telling you how important this piece of music is and then listening to it be important, and then you watch Bob on stage at Radio City Music Hall. You almost needed someone signing because it was so bizarre. Nice going, Bob.”

Photo by Jeffrey R. Staab/CBS via Getty Images