10. Miley Cyrus Gives Director Adam Shankman a Lap Dance
R. Kelly may have seen nothing wrong with a little 
Kristen is the Queen of Gawkiness, so it'd be a travesty if she didn't make this list. But how could we possibly choose just one K.Stew awkward moment? When you drop your award during a live awards show, it probably trumps all. Did her palms get sweaty as she fumbled and dropped her Golden Popcorn statue for Best Female Performance at the 2009 MTV Movie Awards? 'Cause ours sure did
8. Mariah Carey's breakdown on "TRL"
When Mariah Carey showed up at "TRL" unannounced with an ice cream cart in July 2001, it was a little out of sorts. When she stripped off her shirt to reveal a tight tank and gold lame shorts, it was weird. When she started talking gibberish and, with a creepy laugh, said, "You're my therapy session right now Carson. You see, every now and then, somebody needs a little therapy, and today is that moment for me.
7. Faith Hill's CMA Outburst
Losing sucks. And when you have a camera in your face for a reaction shot, it sucks tenfold. Faith Hill learned that the hard way when she lost Female Vocalist of the Year to then-newcomer Carrie Underwood at the 2006 Country Music Awards. Backstage at the time, Faith screamed "What?" in the camera and then walked away. The singer maintains that she was just joking around, it was pretty uncomfortable to watch. 
6. Joaquin Phoenix on "The Late Show with David Letterman"
Now we know that Joaquin's bizarre transformation was just an act, but last year we were scratching our heads as much as Joaquin scratches that gross beard of his during his interview with David Letterman. Sure, we laughed when Dave joked about Joaquin spending time with the Unabomber and taking time off during the interview, but we really felt for him having to reach out to the void that seemed to be his guest.
5. Ryan Seacrest Tries to High-Five a Blind Man
Ryan Seacrest is an equal opportunity high-fiver: Black, white, tall, short -- it doesn't matter. Ryan's quest for equality was put to the test during Scott MacIntyre's "American Idol" Season 8 audition. Scott, if you recall, is blind, but that was no deterrent for Ryan's trailblazing ways. But when the high-five didn't go according to plan, Ryan improvised: He grabbed Scott's hand and walked him through it. Awkward!
4. Britney Spears Performs "Gimme More" at the VMAs
Who wasn't psyched to see Britney make a comeback at the MTV Video Music Awards in 2007? Expectations were high, but what actually went down was quite a different story. Her performance was underwhelming and painful to watch. Dressed in a sequined bra and underwear, Brit-Brit was sluggish, disoriented and out of shape. She moved around the stage aimlessly and wasn't even lip-syncing right. If only we knew how much farther she'd fall ….
3. Ashlee Simpson Lip-Syncs on "SNL"
And speaking of bad lip-syncing, how about Ashlee Simpson?! No list of uncomfortable celebrity moments would be complete without her little jig on "Saturday Night Live" in October 2004 when her lip-syncing ploy was unveiled. Apparently the drummer pressed a wrong button, causing the "Pieces of Me" voice guide track to play for a second time, as opposed to the second song they were supposed to play. Oopsies!
2. Tom Cruise Jumps on Oprah's Couch
Honorable Mention: Tom Cruise's interview with Matt Lauer about psychiatric medication
Tom's a passionate person, and with his passion often comes awkward-to-watch moments. The worst, however, was his infamous couch-jumping incident on "The Oprah Winfrey Show." Watching him on the show, we really didn't know what he was going to do jump on the couch, hug Oprah or whip out an AK-47. 
1. Kanye West: "George Bush Doesn't Care About Black People"
Honorable Mention: Kanye West interrupts Taylor Swift at the VMAs But the more uncomfortable moment has got to be Kanye's off-teleprompter rant during the Concert for Hurricane Relief in 2006. Just watch Mike Myers look at him in utter terror and disbelief, knowing that they’re on live TV and that he's stuck there with him. And when it all culminates with "George Bush doesn't care about black people," it was clear: Hurricane Kanye had come to town.
