15. 51st Annual Grammy Awards
When: February 8, 2009
Complex says: This will go down as one of the best performances in the history of the Grammy Awards. Jay-Z, Kanye West, Lil' Wayne and T.I.? And all of them are channeling a bit of that Rosewood movement in their suits? Can't get better than that. Also: A pregnant M.I.A. in that outfit.