Ebony & Awkward: Music's Most Uncomfortable Interracial Duets

T-Pain and...Taylor Swift? It's not the weirdest black-white music collaboration we've seen. Check out these other awkward fails.

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Complex Original

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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: 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.

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