- 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.