Uploaded August 2026 | Updated September 2026, 2 weeks ago

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Letterman’s staff turns everyday mishaps into unforgettable comedy.
(Air dates: 3/27/2006, 7/17/2007, 1/23/2006, 3/24/2015)

#dentist #whatsontheipod #pilates #kankakee #gazebos #letterman #lateshow

0:00 - 4:20: Tom Ruprecht at the Dentist
4:21 - 9:02: What's on the iPod?
9:03 - 13:53: Bob Borden at Grasshopper Pilates
13:54 - 19:20: Kankakee, Illinois & Twin Gazebos

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Welcome to the Letterman YouTube Channel, home to all your favorite clips from Late Night and Late Show - as well as conversations with the writers, producers and performers who helped make it all happen. And for those of you who like Miscellaneous, you may very well find some Miscellaneous here.