- Participated in community theater throughout Southern Illinois.
- Scored paid gigs on camera as a youth, through his father's production company, PoleStar Productions.
- Performed annually in a sketch-comedy show on New Year's Eve in Springfield, Illinois, with his brother and father.
- Wrote songs for the animated series The Looney Tunes Show.
- Performs with the Groundlings improv troupe, where he met wife Melissa McCarthy.