10) Crispin Glover Fakes A Kick to Letterman's Face - 1987

David Letterman has been long feared as an interviewer for his ability to keep his subjects off balance, and then sit back and watch from behind an array of smirks and eyebrow raising as they dig their own grave. That's why it's so awkward to see Crispin Glover jibbering about his unusual image and taking total control of Letterman's set, culminating in his standing up and firing off a high-kick inches from Letterman's face, at which point Letterman very awkwardly stands up, walks away, and goes to commercial. Apparently, it was all an act on Glover's part in an attempt be Kaufman-esque, but thankfully nobody knew about it but him, and this awkward comedy abortion is the result.

9) George Michael Smokes a J - 2006

When you've been famous for as long as George Michael has, and you're famous for the reasons that George Michael is, you pretty much get to do whatever you want, and if you decide to do that on camera, too, there's apparently not much anyone can do about it. No, George didn't conduct his interview from a public restroomt, but you can catch him blazing up and then providing a suprisingly even criticism of the wacky tobacky as his interviewer waits patiently for him to finish. Maybe it wouldn't have been so awkward if George had ever learned to share (venereal disease doesn't count).

8) Barbara Walters Asks Katherine Hepburn What Kind of Tree She'd Prefer to Be - 1981

The vintage awkward interview. And it's all on Walters. Hepburn actually takes it in stride when Walters asks her what kind of tree she'd like to be; the awkwardness is in Walters fumbling around and only coming up with that to ask. You've got the greatest actress of all time, and you care about how she sees herself as a tree? She should have just gone all out on awkwardness and asked what it's like to be asexual.

7) Paula Abdul interview on Seattle's Fox affiliate... on Painkillers? - 2007

on't let anybody lie to you. There are only two possible explanations for why Abdul behaved the way she did on Seattle TV during the run-up to the current season of American Idol, and one of them is that she was under regression hypnosis and was seeing the world through her own four-year-old eyes. The other is that she is fueled by painkillers. But either way, the alternating confusion and glee of the anchors at Abdul's mumbling, wild swaying and general mental disorganization was probably enough to make the segment producer chew his own teeth to dust.

6) Vanilla Ice Makes Jon Stewart Shart Himself - 1999

It was hard to blame Rob "Vanilla Ice" Van Winkle for being a little irritated. MTV brought him on a show called 25 Lame specifically to humiliate him for "Ice, Ice Baby," and when they gave him the opportunity to smash the fake master copy with a hammer, he declined. Instead, he used a baseball bat, tearing across the set like a maniac and saying things like, "Just to give you an idea of what I'm talking about," which made no sense, because what he had been talking about was turning over a new leaf, not bizarre quasi-staged meltdowns. The high point of the awkwardness occurs when Vanilla winds up the bat at Jon Stewart, who momentarily convulses in fear before Ice makes it all better with a quick, "Sorry, Jon," and brings the bat down gently on the table beside him. Awkward! What do you talk about after you almost get brained by Vanilla Ice? If it were me, I'd probably say, "Damn, Vanilla Ice almost just brained the shit out of me. I need to seriously reconsider my criteria for handing out baseball bats." But I'm not Jon Stewart, who very nearly became the first person in history to find out what it really means to get rocked like a vandal by Vanilla Ice's harpoon-like flow.

5) Matt Lauer is Glib - 2005

This interview would have made the list even if Tom Cruise wasn't one of the biggest movie stars in the world at the time. But since he was, his circular rantings have that added layer of career self-sabotage that could make any day feel like Christmas for a lover of awkwardness. Cruise is like the crazy bullshitting relative who ruins every Thanksgiving by taking some insultingly half-baked contrarian stance that he swears is based on years of research, but which is really based on self-loathing and a need for constant attention. And Lauer is the level headed uncle who relishes poking holes in obvious nonsense just a little too much. Beating Tom Cruise in an argument is a little like beating an anchor at floating. Tom Cruise was not designed for arguing, so who would expect anything less than extreme awkwardness from his effort?

4) Jon Stewart Calls Tucker Carlson a Dick - 2004

The Daily Show host made an appearance on Crossfire which seems to have murdered the show entirely by way of a series of intensely awkward exchanges between Stewart and resident bowtied douche Tucker Carlson. It takes a lot of awkwardness to derail and ultimately eliminate a show that had once been a staple in CNNs daily line-up, especially when you consider the amount of time they already have to fill with hot, hot garbage. But that's what this interview was: a lot of awkwardness. And then a commercial break. And then even more ferocious awkwardness.

3) Letterman's Audience Laughs at Michael Richards' Apology - 2006

There was no way that this could not have been awkward, but it didn't disappoint. It has all the chief criteria filled in spades. Racial tension? Check. Public humiliation? Oh yeah. A career on the brink? Of course. All that, and the surreality is off the charts as Kramer connects to the Late Show via satellite with Seinfeld on Letterman's couch, and, in a moment of nearly unparallelled awkwardness, laughter breaks out in the audience as Richards refers to black people as "afro-americans" and refers to his own screaming of racial slurs as "trash talk". It would have been less awkward if he had just shown how sorry he was by walking across the stage with a fork in his ass.

2) Mike Tyson Opens His Mouth - Various

No man in the history of history has said more hilarious, unhinged, unpredictable shit than Iron Mike. But it would be pointless to try to sort out just one interview, and, besides, why would you want to? Consider this slot permanently reserved for Mike Tyson; it's like a lifetime achievement award for ruining the entire format of celebrity interviews with outlandishly brutal statements. Somebody should gather up every interview he's ever done, and edit all the interviewers' reaction shots together one after another. I would play that tape on a loop at my own funeral. But, failing that, put your boxing-gloved hands together for Mike Tyson's greatest hits.



1) "Chris" Everett Tackles Jim Rome - 1994

Jim Everett of the Rams was one of the best quarterbacks in the NFL for much of the 1980s. But in a 1990 playoff game against San Francisco, Everett's Rams were getting killed, and Everett found himself the recipient of a series of devastating sacks and pummeling hits. Finally, at one point in the game, Everett crumpled to the ground untouched, apparently in anticipation of getting hit again. The play is known as the Phantom Sack, and Everett was never the same player again. Taking his cues from Everett's decline, ESPN2 talkshow host Jim Rome began referring to Jim as "Chris", a reference to female tennis player Chris Evert. Ironically, Evert was known as one of the toughest figures in the history of women's tennis, but that wasn't enough to keep Everett from appearing on Rome's show intent on physically confronting the tiny loudmouth. And when Rome proved his mettle by refusing to back off, Everett crushed him. This video clip may be the best thing in the world.

