The Most Uncomfortable Letterman Interviews Ever

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Published 2018-08-27

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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All Comments (21)

@NickiSwift 5 years ago

Which of these was the most cringe-inducing for you?
@anne-fleurvicarini7616 5 years ago

just show us the clips instead of talking
@haineshisway 5 years ago

We might know who was the most cringe-inducing if you'd stop talking for ten seconds and actually show us the clips.
@MrJonswift200 5 years ago

if we could get get rid of the narration it would be great
@chriswaight2762 5 years ago

why do you have to continue with the endless narration. So bloody annoying
@bo64625 5 years ago

The narration really helps me understand that these are interviews. Thank you for considering my small brain
@Scratchingforcash 5 years ago

THE ONLY CRINGE IS YOUR CONSTANT TALKING. LET THE VIDEOS PLAY!!! YOU CAN BE HORRIBLY ANNOYING!!
@VulCitres 5 years ago

Joaquin Phoenix is going to make a good joker 😎
@BoiledOctopus 5 years ago

Too much irrelevant narration. Couldn't get through it.
@alondramedina1645 5 years ago

Love the new content !! I haven’t seen these interviews !
@gutenbird 4 years ago

Letterman was said to be a pretty bad interviewer because he hardly listened to what the guest was saying.
@petermills542 4 years ago

Beiber's "Sixteenth Chapel " is priceless !
@BaddaBigBoom 5 years ago

95% self-important narration 5% actual footage ...thumbs down.
@ronniechilds2002 5 years ago

The Andy Kaufman/wrestler thing was scripted, and Dave was in on it. He said so in interviews.
@stevesheldon8616 5 years ago

Crispin Glover was playing a character in this interview. Duh
@henryb.little3399 5 years ago

Ha! “The 16th chapel” you walked right into that, Beebz.
@gerardmartin4718 5 years ago

tnx for explaining all the interviews i normally just sit and watch with no sense of whats going on
@dizzymindy6024 5 years ago

I watched the Crspin Glover interview live, and Letterman was sincerely concerned about Crispin’s behavior.
@TechGently 5 years ago

I think Seinfeld was right. Richards was trying to be serious why would people laugh?
@k.doolittle2473 5 years ago

Crispin was just playing.Jeeze