- Appeared in commercials as a child.
- Played John Goodman's son on a Saturday Night Live sketch when he was 12 years old.
- Performed in an off-Broadway musical before beginning his comedy career.
- Took classes at the Upright Citizens Brigade in New York City.
- Created and cohosted a variety show called Creation Nation in 2003, where he first debuted his Billy on the Street character.
- Starred in a talk-show pilot, which also featured Joan Rivers, but it was never picked up.
- Nominated for a Daytime Emmy award for Best Game Show Host in 2013.
- 2015, Emmy — Outstanding Short-Format Live-Action Entertainment Program: Nominee
- 2017, Emmy — Outstanding Variety Sketch Series: Nominee
- Northwestern University, Evanston, Illinois, United States (BA in Theater, 2000)