From Andy Kaufman on Letterman to Kanye West on Kimmel: 5 Awkward Talk Show Moments

Try not to cringe.

Kanye West on Jimmy Kimmel Live

After their highly publicized Twitter feud, Kanye West and Jimmy Kimmel made peace on Live last night…sort of. While both host and guest were seemingly on their best behavior, the dynamic could not have been more awkward. Case in point: Kimmel’s remark that, “I don’t know if you know this, but a lot of people think you’re a jerk.” Kanye went on to talk. And talk. And talk. He also repeatedly reminded everyone that, as he has said before, he is a massive creative genius – though in our experience, if you have to say it, it might not be true.

Andy Kaufman on Late Night with David Letterman

In what has often been cited as the most unbelievable (more on that later) celebrity outburst of all time, comedian Andy Kaufman completely loses his shit at fellow Letterman guest, pro wrestler Jerry Lawler, following an ongoing public feud that had culminated in a televised wrestling match between the two in which Kaufman was injured. There was slapping, there was profanity, there was a stunned audience…but, alas, 10 years after Kaufman’s death it was revealed that the whole thing had been a pre-planned stunt, Jimmy Kimmel-style. Still, it made for some jaw-droppingly awkward late-night television, and celebs looking for inspiration on how to properly lose their minds in public could borrow a page from these two.

Joaquin Phoenix on The Late Show with David Letterman

This 2009 interview grew increasingly bizarre with every passing moment, as the formerly A-list actor – who showed up looking like a homeless person, chewing gum – behaved as though the appearance to promote what he claimed would be his last movie, was a massive imposition. He gave mostly yes or no answers, eventually asking Paul Shaffer, “Are you fucking kidding me?” when the latter let loose a laugh in response to the strange behavior. Things got even more awkward at around the 4:30 mark, when Dave, visibly irritated, remarks that next time, “I’ll come to your house and chew gum,” prompting Phoenix to stick his used gum on Dave’s desk. Dave didn’t miss a beat, eventually ending the segment with, “Joaquin, I’m sorry you couldn’t be here tonight.”

Danny DeVito on The View

Why should late-night talk shows have all the fun? In this hilarious but nevertheless awkward appearance on The View, Danny DeVito admitted that he was still hammered after what we can only imagine must have been the world’s most awesome night of heavy drinking with none other than George Clooney. He proceeded to, well, act like a drunk person, slurring his speech, referring to former President George W. Bush as “numb nuts,” and sharing an anecdote about banging his wife on every surface of the Lincoln Bedroom. Frank Reynolds would be proud.

David Letterman on The Late Show with David Letterman

One of the most awkward guests ever to grace Letterman’s stage turned out to be Dave himself, when, in 2009, he admitted to having had a sexual affair with a member of his staff. Oh wait, make that WOMEN. Multiple. He tried to keep it light, but just picturing Dave’s wife in the green room with steam coming out of her ears while he made such an admission was enough to make the whole thing painful to watch.