The 20 Most Awkward Music Collaborations

6. Taylor Swift f/ T-Pain "Thug Story" (2009)

Taylor Swift and T-Pain's pre-taped performance of "Thug Story" at the 2009 CMT Awards was one of the most talked-about viral clips of that year, 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. Watch it below.

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