19. "Dirt Off Your Shoulder" (2004)
By this time, producer's Timbaland's rhythms were still so avant-garde, he jokingly asked Jay-Z in Fade to Black whether the rapper was "confused" by his beats. What came out of their Black Album sessions, though, was immediate enough to resonate for years. "I think when Tim played the track early on, it had like a brushing sound on it. I started messing with lyrics about brushing off haters," Jay said in The Hits Collection Vol. 1 liner notes. An actual radio takeover played out in the song's video. In reality, not only did "Dirt" become one of his biggest hits, but it even had Barack Obama following his lead during the 2008 Democratic primaries.