- 2007: Cast opposite Terrence Howard in the inner-city sports drama "Pride"
- 2005: Wrote and starred in the comedy "The Kid and I"
- 2005: First romantic leading man role in "Happy Endings"
- 2001: Co-hosted the FOX Sports' show "Best Damn Sports Show Period"
- 1997: Returned to series TV as star of the WB sitcom "The Tom Show"
- 1996: Co-starred with Rick Moranis in "Big Bully"
- 1995: Played a supporting role in the comedy "Nine Months"
- 1994: Appeared as the sidekick to Arnold Schwarzenegger’s character in the James Cameron feature film "True Lies"
- 1994: Formed the production company Clean Break Productions
- 1994: Created and produced the short-lived CBS sitcom "Tom"; also wrote the pilot episode
- 1993: Signed a long-term TV production deal with Warner Bros., with projects to be produced under the Wappello County Productions banner
- 1992: First substantial feature acting credit, "Hero"
- 1992: Created, executive produced and starred in the series "The Jackie Thomas Show" (ABC)
- 1992: TV movie acting debut with "Backfield in Motion"
- 1991: First HBO special, "Tom Arnold: The Naked Truth"
- 1991: Made feature film debut in a cameo (with Roseanne) in "Freddy's Dead: The Final Nightmare"
- 1991: TV-movie acting debut, "Backfield in Motion"
- 1990: Debuted as a producer for the show "Roseanne" (ABC)
- 1990: Appeared occasionally on "Roseanne" (ABC) as the character 'Arnie Thomas'
- 1990: Executive produced the Saturday morning animated TV series "Little Rosey" (ABC)
- 1988: Moved to Los Angeles to pursue a standup comedy career
- 1988: Won the first place in the Minneapolis Comedy Competition
- 1988: Hired as a writer for Barr's sitcom "Roseanne" (ABC)
- 1987: Made TV debut in the HBO special "The Roseanne Barr Show"
- 1983: First met Roseanne Barr
- 1982: Began doing stand-up comedy when he was 23
- Co-founded Wapello County Productions with Roseanne




