Tom Waits cracks up Letterman, confounds George Clooney with his Tom Waits humor

Tom Waits tells jokes to Letterman, while George Clooney finally clues in

(Image credit: Late Show)

published 15 May 2015

Tom Waits came prepared for his final appearance on David Letterman's Late Show. And not only with a new song. During his sit-down portion with Letterman, Waits started out with a tale about a seeing a long line of people in New York, and finding out they were waiting for salad. "I was, frankly, embarrassed for them." By about his third story, it's clear that Waits is telling jokes. They are all pretty odd, and if you like Tom Waits, pretty funny.

For the better part of the conversation, George Clooney — who perhaps regretted his very sweet decision to handcuff himself to Letterman earlier in the show — looked confused. But by the time Waits got to his "retire" joke, Clooney was cracking up, too. He should listen to more Tom Waits. Watch the spectacle below. —Peter Weber

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Peter has worked as a news and culture writer and editor at The Week since the site's launch in 2008. He covers politics, world affairs, religion and cultural currents. His journalism career began as a copy editor at a financial newswire and has included editorial positions at The New York Times Magazine, Facts on File, and Oregon State University.