Appeared in PBS documentary series "The Voyage of the Mimi"
TV miniseries debut, "Hands of a Stranger" (NBC)
Cast in regular role on the short-lived NBC series "Against the Grain"
Directed short film "I Murdered My Lesbian Wife, Hung Her on a Meathook and Now I Have a Three-Picture Deal at Disney"
Charmed critics and audiences as a comic book artist who falls for a bisexual woman in Kevin Smith's "Chasing Amy"
Formed Pearl Street Productions with Matt Damon
Played a bartender in the ensemble comedy-drama "200 Cigarettes"
Re-teamed with director Kevin Smith for "Dogma"; also re-teamed with Damon to play a pair of renegade angels
Joined ensemble cast of "The Boiler Room," a drama about Wall Street brokers
With Damon and backed by HBO and Miramax, sponsored Project Greenlight, a screenwriting competition that would result in a produced motion picture
Re-teamed with Gwyneth Paltrow for "Bounce"
With Damon, co-executive produced and acted in "The Third Wheel" (filmed in 1999), scripted by buddy Jay Lacopo
Made a brief appearance in Kevin Smith's "Jay and Silent Bob Strike Back"; reprised role of Holden from "Chasing Amy" as well as appeared as himself
Executive produced and appeared in the HBO series "Project Greenlight" about the script writing contest he co-sponsored
Assumed the role of Jack Ryan (previously played by Alec Baldwin and Harrison Ford) in "The Sum of All Fears"
Served as an executive producer on "Stolen Summer"; winner of the Project Greenlight competition
Co-created (with Sean Bailey) and executive produced (with Matt Damon) short-lived ABC drama "Push, Nevada"
Cast as Matt Murdock/Daredevil in the blockbuster "Daredevil," based on the Marvel comic book character
Co-starred with Jennifer Lopez in box office flop "Gigli"
Played the lead in the John Woo thriller "Paycheck"
Re-teamed with director Kevin Smith for the romantic comedy "Jersey Girl"
Starred as a lonely guy who rents himself a family for the holidays in the comedy "Surviving Christmas"
Portrayed the 1950s "Superman" TV star George Reeves in "Hollywoodland"; received a Golden Globe nomination for Best Actor in a Supporting Role
Executive produced horror film "Feast," a result of the third season of the Project Greenlight contest
Played a congressman opposite Russell Crowe in the thriller "State of Play"
Played Jason Bateman's best friend in Mike Judge's "Extract"
Played a white-collar corporate employee who loses his job in John Wells' directing debut "The Company Men"
Featured in Terrence Malick's "To the Wonder"
Starred opposite Justin Timberlake in the thriller "Runner Runner."
Executive produced the HBO film "The Leisure Class"