2005: The College Dropout artist graduates with top honors, wearing a jazzy white tuxedo jacket and metallic aviators to pick up his Best Male Video award.
2008: Dressed in a sharp but conservative suit, the ever-controversial West lets the backdrop of fireworks close out that year's show with a bang during his performance of "Love Lockdown."
2010: A year after his Taylor Swift debacle, the risk taker looks fired up to return to the VMA stage dressed in head-to-toe red.