Taylor Swift and T-Pain's pre-taped performance of "Thug Story" at last night's CMT Awards is sure to be one of the most talked-about viral clips of the week, but we weren't really that impressed. It's not like we can't find the humor in T-Swizzle rapping about baking cookies, but the whole bit came across as more of a streetcchhhh than hilarious.

She tried though, and quite frankly, we don't blame her or Teddy Pain for the way the video turned out. Collaborations between black and white music stars have a history of turning out cornier than a box of Jiffy Mix. Don't believe us? Revisit Music's most uncomfortable interracial duets below...

COLLABORATORS: Bone Thugs-N-Harmony x Phil Collins
SONG: "Home"
YEAR: 2002
• Wow. Phil Collins has the least convincing head nod we've ever seen. And we know this video is supposed to be "deep", but PC blankly staring off into space had us laughing. Juxtapose that with four Ohio "thugs" draped in work/sports gear and you have one unintentionally awkward collaboration.

SONG: "Life Is Good"
YEAR: 2001
• This record never even got a video and it's still arguably the most bizarre collaboration ever, race notwithstanding. To make matters worse, the song was terrible. Did the Mosh Out Posse like girls that wear Abercrombie & Fitch? Eh, probably not.

SONG: "Stolen Car (Remix)"
YEAR: 2004
• Diddy's award show duet with Sting was a classic moment in hip-hop history. Twista's music video with the same guy was just a classic fail. The '80s icon did look mighty comfortable with the groupies in the club scene though. Go 'head Sting!

COLLABORATORS: Nelly x Justin Timberlake
SONG: "Work It"
YEAR: 2003
• We don't know how this disaster happened, considering JT made bangers with Clipse and 50 Cent right before he hopped on this track with the St. Lunatic. Chalk it up to Nelly's rising cornball status or the god-awful trends at the time, but the two superstars didn't mesh well at all on this track.

SONG: "Play Me"
YEAR: 2003
• Before Lil' Wayne was rocking with Korn in the video for "Prom Queen," Nas was collaborating with them and making really, really shitty songs. See? Doing something first isn't always a good thing.

COLLABORATORS : New Kids On The Block x Nice & Smooth
SONG: "Dirty Dawg"
YEAR: 1993
• This is what a desperate comeback looks like. NKOTB was well past their prime by the time this video debuted and its general lameness combined with corny raps from Nice & Smooth made sure they stayed there. After selling millions of records with prior releases, the Face The Music album that "Dirty Dawg" was featured on was a commercial failure. Shocker.

COLLABORATORS: Hilary Duff x Slim Thug
SONG: "With Love (Remix)"
YEAR: 2007
• Listening isn't necessary to realize how embarrassing this collab was for both parties, especially Slim Thug. The real loss? That same year, Hilary Duff earned a cool $12 million and Slim Thug probably didn't earn a quarter of that. Now who's really the boss?

COLLABORATORS: Paul McCartney x Michael Jackson
SONG: "Say Say Say"
YEAR: 1983
• Ah, the one that started it all. Definitely a classic, but it's too bad the $500,000 spent on this video couldn't get rid of the never ending chessiness. Even more awkward than the single's pause-worthy cover is Latoya Jackson's role as her brother's love interest. With all that said, MJ is still a G for snatching up The Beatles back catalog from under Paul, after McCartney allegedly schooled Jacko about the benefits of publishing money.

COLLABORATORS: Celine Dion x R. Kelly
SONG: "I'm Your Angel"
YEAR 1998
• We know "I Believe I Can Fly" was a huge hit and everything, but the homie R. Kelly rode the inspirational ballad train way too hard with this one. And while it was massively successful, that didn't make it any less awkward. The alternate version of the music video got more spins, but we prefer this one just for the infomercial-esque scenes of Celine and Robert in the studio together.

COLLABORATORS: Jonas Brothers x Common
SONG: "Don't Charge Me For The Crime"
YEAR: 2009
• Career advice for Common: after releasing the worst album of your career, don't fuck things up even more by collaborating with The Jonas Brothers. That next album better sound like Be x1000, homie.