- His father is a Presbyterian pastor.
- Is an avid snowboarder and surfer.
- Performed at the 1998 Just for Laughs festival in Montreal.
- Made his network debut in 2001 on The Late Show with David Letterman.
- Released his first comedy album, True Stories I Made Up, in 2005.
- Has performed his comedy act at more than 700 college campuses.
- Received the Michelle Akers Award from his alma mater, University of Central Florida, in 2011.
- Began the Tosh Saves the World comedy show in 2011, an annual event that benefits charity.