Watch Tom Waits Perform Letterman Ode 'Take One Last Look'

Singer also marks 10th and final 'Late Show' visit with an interview eavesdropped by a handcuffed George Clooney

UPDATE: Bob Dylan will make a rare late night TV appearance – and his first Letterman musical guest spot in 22 years – when he performs on the May 19th penultimate episode of Late Show With David Letterman. Dylan last appeared on Letterman's CBS program in 1993, just months after the Late Show debuted. Eddie Vedder, originally billed as Letterman's final musical guest, is scheduled to perform on Monday's episode.

"This is for you, Dave," Tom Waits told David Letterman before performing a new song fittingly titled "Take One Last Look." Waits made his first Letterman appearance way back on December 21, 1983 when the late night host was at the reins of NBC's Late Night, and with only four Late Show episodes left before Letterman retires, Waits treated the host and the audience to a never-before-played track.

"Let's watch the sun come up in another town / Try our luck a little further down / Leave the cards on the table, leave the bread on the plate / Put your hand on the gearshift, let your foot of the brake," Waits sang, accompanied only by an accordionist and upright bassist. "And take one last long / At the place that you are leaving." With the finish line in sight – and Late Show's final guests in place – Waits' song was especially poignant as Letterman prepares to leave late night after over 32 years and an unforgettable legacy.

"I don't know when I will see Dave again. I guess from now on we'll have to settle for bumping into each other at pilates," Waits joked on his official site. The gravel-voiced singer was making his 10th and final visit to Late Show With David Letterman.

In addition to the premiere performance, Waits also sat down on Letterman's couch one last time, where he chatted with the late night host while George Clooney sat silently handcuffed to Letterman's wrist. "It's amazing how nice folks are to you when they know you're going away," Waits noted before launching into a five-minute, seated stand-up routine where the punchline was clearly the Oscar-winning actor fastened uncomfortably to Letterman.

"I haven't been in New York in a while, I was really surprised. There was a huge line today on the street and I figured, 'Maybe it's a girlfight,'" Waits tells Letterman. "I asked a couple guys in line. I said, 'What are you in line for?' And they said they were in line for salad. I was frankly embarrassed for them. They said it comes in by helicopter for Cheyenne, it's really fresh."

Waits also joked that he's been working on an antiperspirant called "New Car Smell" and a "perspirant" named "Hard Work." The Rain Dogs great then leaves Letterman with one well-timed joke: "Just be glad that you're not in the tire business. You can't retire from the tire business. It sounds like you're signing up for more time."

Letterman's run will conclude Wednesday, May 20th with Tom Hanks (making his 60th Late Show appearance) and final musical guest Eddie Vedder.