| Formed the hip hop music group The Whooliganz with childhood friend Alan Maman; recieved a recording deal with Tommy Boy Records and released one album, Make Way for the W. |
| Worked as a roadie for the rap groups Cypress Hill and House of Pain |
1995 | Made his feature debut in the independent film "A Boy Called Hate"; father also acted in film playing his onscreen dad |
1997 | Acted in the third installment of Gregg Araki's 'teen apocalypse' trilogy, "Nowhere" |
1997 | Appeared in the comedy "Bongwater" with an ensemble cast including Luke Wilson and Jack Black |
1998 | Played a cocky government agent chasing Will Smith in Tony Scott's "Enemy of the State" |
1999 | Provided comic relief for "Varsity Blues" as a rowdy, girl-chasing high school football player opposite James Van Der Beek |
1999 | Starred in the independent film "Black and White" |
2000 | Co-starred with Ben Affleck and Giovanni Ribisi in the "Boiler Room" |
2000 | Co-starred with David Arquette in the comedy "Ready to Rumble" |
2001 | Joined an ensemble cast for Steven Soderbergh's remake of "Ocean's Eleven" |
2001 | Played Western bandit Cole Younger to Colin Farrell's Jesse James in "American Outlaws" |
2002 | Cast in the drama "Sonny," with James Franco |
2004 | Re-teamed with the original cast for "Ocean's Twelve"; again directed by Steven Soderbergh |
2005 | Co-starred with Paul Walker and Jessica Alba in the thriller "Into the Blue" |
2005 | Made writing and directing debut with "Dallas 362"; also co-starred with Jeff Goldblum and Kelly Lynch |
2006 | Cast in Nicole Holofcener's "Friends with Money" opposite Jennifer Aniston |
2007 | Co-starred with Freddie Prinze Jr. and Alec Baldwin in Michael Corrente's "Brooklyn Rules" |
2007 | Played a detective in "Lonely Hearts," which is based on the true story of the notorious Lonely Hearts Killers of the 1940s |
2007 | Re-teamed with the original cast for "Ocean's 13" |
2008 | Had a small role in the Eddie Murphy comedy "Meet Dave" |
2009 | Cast in a recurring role as a talent manager on HBO's "Entourage" |
2010 | Landed a starring role on CBS' reboot of "Hawaii Five-0" |
2010 | Produced first feature "Mercy"; also wrote and co-starred opposite his father James Caan |
2011 | Nominated for the 2011 Golden Globe Award for Best Performance by an Actor in a Supporting Role in a Series, Mini-Series or Motion Picture Made for Television ("Hawaii Five-0") |
