Formed The Lonely Island web-comedy trio with high-school friends Andy Samberg and Jorma Taccone.
Confronted by passer-by Kiefer Sutherland while filming a scene for one of their earliest shorts, in which they rob an elderly woman.
Hired as a writer for Saturday Night Live in 2005 and co-produced "Lazy Sunday," the digital short that became one of YouTube's first viral videos (over 5 million hits in first two months).
Met his wife, Liz Cackowski, while both worked as writers for the 2005 MTV Movie Awards.
Recorded three albums with his troupe, including Incredibad, the eighth-highest selling hip-hop album of 2009.
Donated $250,000 to his high-school (Berkley Unified School District), a gift earned by his comedy group through a Doritos Super Bowl ad promotion.