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Before he got his start in acting, Scott was very involved with music.He first began as an aspiring rapper in the early 90s when he was a roadie for the rap groups ‘Cypress Hill’ and ‘House of Pain’.His first role in a major motion picture was that of Charlie Tweeder, a reckless Texas football player in Varsity Blues (1999).In the same year, he played the role of Drew in the film Saturn (also known as Speed of Life).In the 1990s, he was a part of hip hop group The Whooliganz with The Alchemist.The duo went by the names Mad Skillz and Mudfoot, respectively.Caan appeared in the feature film trilogy Ocean's Eleven, Ocean's Twelve, and Ocean's Thirteen.In 2005, he co-starred with Paul Walker (with whom he appeared in Varsity Blues) in the action film Into the Blue.
Caan was also a member of the hip-hop group The Whooliganz as Mad Skillz (with producer and fellow MC The Alchemist as Mudfoot).
Caan subsequently appeared in several studio films, including Ready to Rumble (2000) co-starring David Arquette, Boiler Room (2000) co-starring Vin Diesel, Gone in 60 Seconds (2000) as Tumbler and American Outlaws (2001), co-starring Colin Farrell, in which Caan played 19th-century outlaw Cole Younger.
In 2003, Caan made his directorial debut with the film Dallas 362, which subsequently won a prize at the 2003 Las Vegas Film Festival.
Caan wrote and directed the 2006 comedy The Dog Problem, and appeared as a supporting character in the film as well.
He appeared on the television series Entourage in a recurring role as talent manager Scott Lavin from seasons six to eight.