Top 10 Most Awkward Moments on Late Night

It’s kind of assumed by now, for good reason, that when Phoenix does interviews, things are going to get weird… But it’s not always his fault. He’s genuinely shy and a little socially awkward, so he sometimes has trouble following typical interview conventions; yet, TV hosts keep trying. We’re at the point where the awkwardness of these encounters perhaps stems more from hosts persisting. On the other hand, that’s their job. Phoenix was charming while talking about his acting, but once Kimmel became a bit more pointed and personal, Phoenix became less comfortable, defensive, and less engaged. His appearance on Fallon during this same time also went off the rails when the host asked a series of personal questions as well.

This conversation between Burr and Silverman was so cringe and confusing that we’re still not sure what happened almost two years later – and neither is the Internet! Either these two are very close and are just taking the piss out of each other, or this was an impromptu therapy session exploring their likes and dislikes for each other. And, honestly, not knowing for sure makes it all the more uncomfortable! To be fair to Sarah though, Burr is usually on the defensive when it comes to interviews, and doesn’t exude much in terms of emotion (unless you count sarcasm and paranoia!); so, all things considered, it could have gone much worse… right?

For certain celebrities, heading onto “Late Night” in the ‘80s was akin to throwing raw meat into a hungry lion’s cage. Dave mellowed out in his later years, but early on he could be quite confrontational – or as Shirley MacLaine calls him: an asshole. Part way through this interview, Dave wanted to talk about Shirley’s belief in reincarnation, but the actress didn’t think there was time to do so. And, as Dave kept pushing the topic, MacLaine let Dave know what she thinks of him. What’s truly remarkable about this scene is that neither guest nor host attempted to make up or play nice for TV, and the barbs just kept coming until the interview (mercifully) ran out of time.

It’s hard to imagine any interview in this day and age starting out with a headbutt backstage; but, that’s just what happened here. Cavett’s infamous interview featured two literary heavyweights, squaring off over their intense dislike of one another. Mailer was a critic of the feminist movement, and Vidal took his views to task in an essay where he likened Mailer’s misogyny to that of serial killer Charles Manson. Mailer, who had been drinking, was furious with Vidal’s article and subsequently couldn’t maintain his composure in person, headbutting and cursing Vidal backstage while openly insulting everyone (including the host and female guest) on stage. Talk about intense.

If you’ve seen Ferrara’s 1992 film “Bad Lieutenant,” you’d know that the director is not afraid of controversy – which Conan acknowledged while inviting him onstage at his old show. So, not surprisingly, controversy is exactly what ensued… Ferrara was accused of showing up drunk, refusing to go on stage, and – at one point – even leaving the NBC studio, requiring staff members to track him down. And, if you thought that sounds like a mess, just watch the interview. Ferrara is barely audible at times – slurring and rambling incoherently – to the point where Conan suggests viewers will need subtitles to understand him. Conan later admitted that, in his entire career, Abel Farrara was by far the absolutely worst guest he’s ever interviewed.

Remember the Late Night Wars? Well, Jimmy Kimmel sure had a take; and, he didn’t take kindly to Jay Leno’s actions, ruthlessly mocking and impersonating Jay during Leno’s drawn-out “Tonight Show” dustup with Conan O’Brien. For some odd reason, Leno’s producers then thought it a good idea to have Kimmel on Jay’s new show; and, well, it plays out exactly as you’d expect. Leno clearly hates Kimmel’s impression of him, and Jimmy takes every opportunity to insult Jay on his own show. Watching Leno forcing himself to laugh while Jimmy drops bombs on him is the equivalent of having to smile while being punched in the face. Ouch!

It took Letterman about a fraction of a second to insult Hilton when she (unwisely) appeared on his show in 2007 after serving time in jail. Dave introduced her as a “woman of many talents” with a sharp grin on his face, and then went straight to pressing (and mocking) Paris on her jail stay. Hilton initially put on a brave face, but soon refused to talk about her time in the clink, while shooting Dave some dirty looks. This is so painful to watch, because she is drastically outmatched here and obviously cannot trade in sarcasm and insults with a master like Letterman. In fact, it’s just unfair at some points, and we kind of wish there was a referee present to stop the fight.

Conan went to Harvard. And while that doesn’t always mean anything, he is clearly a sharp guy. So, Garner probably shouldn’t have called out O’Brien for his (ultimately correct) language usage before mocking his education at one of the best universities in the world. But, she did. Luckily it was all in good fun, but – being the nerd he is – Conan couldn’t let the opportunity pass to whip out a dictionary and school Garner (quite literally). Jennifer goes from confidently, and enthusiastically, talking about her latest role to utter silence – with more than a hint of embarrassment – as Professor O’Brien rubs it in.

Just like you never know how a Letterman interview will go, you never know how a Madonna guest appearance will turn out! But, we know one thing for sure: everyone at the FCC was having a collective heart attack during this profanity-ridden, innuendo-driven, filthily funny interview! Oh, where to begin, really?? Countless F-Bombs and anatomy jokes are one thing, but it’s Madonna’s constant insistence that Dave’s obsessed with her sexually, and – while never denying this claim – Dave’s flirty behavior that really makes this one for the ages. Do they like each other? Do they loathe each other? Just what are we watching here? It feels like either a fight or a snog-fest is about to break out and both outcomes are equally as worrisome.

Before we unveil our top pick, here are a few honorable mentions:

When Stephen Colbert Interviewed Donald Trump
“The Late Show with Stephen Colbert” (2015-)

When Crispin Glover Got Weird
“Late Night with David Letterman” (1982-93)

When Kari Wuhrer Went After Steven Wright
“Late Night with Conan O’Brien” (1993-2009)

When Bill O’Reilly Talked Politics
“Late Show with David Letterman” (1993-2015)

When Guy Ritchie Was Unimpressed With David Spade
“Jimmy Kimmel Live” (2003-)

Ah, Joaquin again. Sure, his whole shtick turned out to be a wacky piece of performance art for a mockumentary that he and Casey Affleck were making, but in 2009, the world collectively thought that Joaquin had fully lost his mind. He claimed he was transitioning to a career in hip-hop, yet he could barely string two sentences together in real time. Was he drunk? High? Sick? Dying? For every time someone asked one of these questions, the outcome was a torrent of opinion pieces and endless speculation that filled the Internet for months. Yet, the one thing we didn’t get –for over a year-and-a-half – was answers. Joaquin returned to “The Late Show” in 2010 and apologized for his behavior, but even that interview was a little awkward!