Caan was born in Los Angeles, California, the son of actor James Caan and Sheila Marie Ryan, an actress and former model. His paternal grandparents were Jewish immigrants from Germany. He has an older half-sister named Tara Caan and three younger half-brothers named Alexander James Caan (born 1991), Jacob Nicholas Caan (born 1995), and James Arthur Caan (born 1998).\n', '

Caan was a roadie for the rap groups Cypress Hill and House of Pain. Caan was also a member of the hip-hop group The Whooliganz as Mad Skillz (with producer and fellow MC The Alchemist as Mudfoot). The Alchemist and he, when performing as the rap duo the Whooliganz in the early \'90s, received a record deal with Tommy Boy records. They recorded the album Make Way for the W., but after their first single "Put Your Handz Up", the album was shelved and the duo was dropped by Tommy Boy. In 1995, the Whooliganz\' song "Whooliganz" was released as a single in the UK, but Caan and the Alchemist had already parted ways. Caan reunited with his former partner The Alchemist in 2014 on the Step Brothers project Lord Steppington, performing in the song "Byron G" with musician Evidence.\n', '

After enrolling at the Playhouse West acting school in Los Angeles, Caan began acting in the late 1990s, appearing in a number of independent films and low-budget films. 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). 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.\n', '

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