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The Most Uncomfortable Letterman Interviews Ever - VideoRolls.com

By: Nicki SwiftPublished: 2 months ago

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In many regards, David Letterman is the perfect antidote to the airless celebrity interview. During his long, legendary tenure as a late-night talk show host, he earned a reputation for keeping guests on their toes and and cracking plenty of jokes at their expense. Of course, Letterman has also fallen victim to plenty of guests who went out of their way to be openly confrontational, provocative, and gleefully obnoxious. Here's a closer look at some of David Letterman's most uncomfortable interviews...

​Madonna | 0:31
Justin Bieber | 1:33
​Michael Richards | 2:20
Crispin Glover | 3:09
​Andy Kaufman | 4:30
Joaquin Phoenix | 5:22

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