The Most Uncomfortable Letterman Interviews Ever

David Letterman never liked giving the kind of interview where a star would plug their latest movie and move on, but these interviews were odd, even for Letterman. Sometimes, the stars came out ready to fight (literally, in one case), while others were quickly made uncomfortable with an insulting introduction by the late-night host -- but these segments all took a turn for the weird, probably leaving the guests wishing that they had just gone on The Tonight Show instead.

From the actor who challenged Letterman to an arm wrestling match to the bizarre apology that just made things worse, let’s take a look at the weirdest and most uncomfortable David Letterman interviews ever.

#DavidLetterman #Interviews #Awkward

​Madonna | 0:00
Justin Bieber | 1:33
​Michael Richards | 2:20
Crispin Glover | 3:09
​Andy Kaufman | 4:30
Joaquin Phoenix | 5:22

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