- Started out as a producer for hip-hop artists including Jermaine Dupri, Jay-Z and Ludacris.
- After fracturing his jaw in a car crash, he wrote "Through the Wire," which got him a record deal.
- Walked out of the American Music Awards in 2004 after losing the Best New Artist award to country performer Gretchen Wilson. He later apologized to her for his actions.
- Took some heat for publicly criticizing President George W. Bush during a 2005 NBC Hurricane Katrina benefit concert.
- Was widely denounced when he interrupted Taylor Swift's acceptance speech at the MTV Video Music Awards in September 2009.
- Made his directorial debut in 2010 with the musical short film Runaway, which is based on the song of the same name from his My Beautiful Dark Twisted Fantasy album.