8. T.I. f/ Justin Timberlake "Dead and Gone" (2009)
Producer: Justin Timberlake, Rob Knox
Album: Paper Trail
Justin Timberlake wasn't making much music towards the latter end of the Aughts, but after T.I. helped him score a No. 1 with "My Love," he owed the King of the South a favor. That favor was a scene-stealing chorus on Paper Trail's fourth and final single, "Dead and Gone."
The song was such an event that it charted on Billboard before it was even officially releasing, later climbing all the way to No. 2. (T.I.'s previous Paper Trail singles, "Whatever You Like" and "Live Your Life" both hit No. 1; you can't win them all.) "Dead and Gone" eventually registered three million in sales and was nominated for two Grammys.
Although T.I. and Timberlake didn't take home any trophies for the track, they did perform at the ceremony. Perhaps that's an even greater testament to record's total dominance at the time. —Ernest Baker