For the final scheduled musical guest in David Letterman's Late Show history, the retiring host welcomed Bob Dylan, who he considers "the greatest songwriter of modern times." Dylan, making a rare late-night television appearance, performed the oft-covered "The Night We Called It a Day," a single off his Sinatra-inspired 2015 LP Shadows in the Night. Dylan last visited Letterman in November 1993, just months after the Late Show launched.
"I spend a lot of time, like everyone does, driving around with my son Harry, and sometimes you take an opportunity to teach him or reinforce things for him. And I say, 'Harry, what are the two most important things to know in the world,'" Letterman said in introducing Dylan. "'One, you have to be nice to other people,' and what's the other one? The greatest songwriter of modern times is Bob Dylan. That's all you need to know in life."
While fans likely hoped for a more popular selection from the Dylan songbook, the jazz standard fit perfectly with the reflective mood of the evening, including final Late Show visits from Regis Philbin, deli owner Rupert Jee and Bill Murray. "The moon went down, stars were gone / But the sun didn't rise with the dawn / There wasn't a thing left to say / The night we called it a day," Dylan crooned just 24 hours before the curtain closes on Letterman's Late Show after 22 years and a career in late-night television that spans 33 years.
Dylan first appeared on Letterman's Late Night program on NBC in March 1984 to perform Infidels' "Jokerman." Dylan's late-night appearances have been virtually non-existent in subsequent decades, but when he does show up on television, it's usually for Letterman: After performing "Like a Rolling Stone" on Letterman's 10th anniversary NBC special in 1992, the rocker once again visited the host – this time on CBS – to play "Forever Young" on the then-nascent Late Show.
In the lead-up to Letterman's grand finale, the late-night host invited Paul Shaffer, his longtime bandleader, to sit on the couch and talk about his career in music. In the interview, Shaffer talked about meeting with Dylan.