- 2009: Played a Congressman, opposite Russell Crowe, in the thriller "State of Play"
- 2009: Played Jason Bateman's best friend in Mike Judge's "Extract"
- 2007: Directorial and writing debut, the feature adaptation of "Gone, Baby, Gone"; based on the book by "Mystic River" author Dennis Lehane and starring his brother Casey Affleck
- 2006: Executive produced "Feast" a horror film, which is a result of the third season of the Project Greenlight contest
- 2006: Portrayed the 1950s 'Superman' TV star George Reeves in "Hollywoodland"; received a Golden Globe nomination for Best Actor in a Supporting Role
- 2004: Re-teamed with director Kevin Smith for the romantic comedy "Jersey Girl"
- 2004: Starred as a lonely guy who rents himself a family for the holidays in the comedy "Surviving Christmas"
- 2003: Cast as Matt Murdock/Daredevil in the blockbuster, "Daredevil," based on the Marvel comic book character
- 2003: Played the lead in the John Woo thriller "Paycheck"
- 2003: Co-starred with Jennifer Lopez in the box office flop, "Gigli"
- 2002: Executive produced and appeared in the HBO series "Project Greenlight" about the script writing contest he co-sponsored
- 2002: Served as an executive producer on "Stolen Summer"; winner of the Project Greenlight competition
- 2002: Assumed the role of Jack Ryan (previously played by Alec Baldwin and Harrison Ford) in "The Sum of All Fears"
- 2002: Co-created (with Sean Bailey) and executive produced (with Matt Damon) the short-lived ABC drama, "Push, Nevada"
- 2001: With Damon, co-executive produced and acted in "The Third Wheel" (filmed in 1999), scripted by buddy Jay Lacopo
- 2001: Had leading role in the WWII-era drama "Pearl Harbor"
- 2001: 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
- 2000: With Damon and backed by HBO and Miramax, sponsored Project Greenlight, a screenwriting competition that would result in a produced motion picture
- 2000: Led the ensemble cast of "The Boiler Room," about Wall Street brokers
- 2000: Re-teamed with Gwyneth Paltrow for "Bounce"
- 1999: Played a bartender in the ensemble comedy-drama "200 Cigarettes"
- 1999: Re-teamed with director Kevin Smith for "Dogma"; also re-teamed with Damon to play a pair of renegade angels
- 1998: Appeared opposite Gwyneth Paltrow and Joseph Fiennes in the award winning "Shakespeare in Love"
- 1998: Co-starred in the Michael Bay blockbuster "Armageddon"
- 1997: Charmed critics and audiences as a comic book artist who falls for a bisexual woman in Kevin Smith's "Chasing Amy"
- 1996: Sold his script, "Good Will Hunting" to Miramax; co-written with Matt Damon; filmed and released in 1997 with both co-starring
- 1995: Directed short film "I Murdered My Lesbian Wife, Hung Her on a Meathook and Now I Have a Three-Picture Deal at Disney"
- 1993: Had regular role on the short-lived NBC series "Against the Grain"
- 1992: Feature film debut, "School Ties"; also co-starred with childhood pal Matt Damon
- 1987: TV miniseries debut in "Hands of a Stranger" (NBC)
- 1986: Made network TV debut in an ABC Afterschool Special, entitled "Wanted: The Perfect Guy"; played Madeline Kahn's son
- 1984: Appeared in PBS documentary series "The Voyage of the Mimi"
- Formed Pearl Street Productions with Matt Damon
- Raised in Cambridge, MA
- Born in Berkeley, CA




