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Caan was born in Los Angeles, California to actor James Caan and Sheila Ryan, an actress and former model. His paternal grandparents were Jewish immigrants from Germany. His parents divorced a year after his birth; he has four half-siblings from his father's other marriages.

Caan was a roadie for the rap groups Cypress Hill and House of Pain, and was a member of the hip-hop group The Whooliganz (with producer and fellow emcee, The Alchemist), before enrolling at the Playhouse West acting school in Los Angeles.

Subsequently, Caan has appeared in other low-budget independent films, as well as the box office successes Ocean's Eleven, Ocean's Twelve, and Ocean's Thirteen. In 2005, Caan co-starred with actor Paul Walker (with whom he appeared in Varsity Blues) in the action film Into the Blue.