Caan was born on Aug. 23, 1976 in Los Angeles, CA, the son of veteran film actor James Caan and former model/actress Sheila Ryan. His parents split up a year after his birth, but maintained a very active presence in his upbringing. His father took a hiatus from acting for several years in the 1980s to concentrate on coaching the younger Caan’s Little League team. At the start of the 1990s, Caan drifted from school to school, spending time at the celebrity-magnet Beverly Hills High School before graduating from Excelsior High School.
Despite his perpetual love of baseball, Caan’s hopes of having a professional career as a major leaguer lessened, but he also had designs on the music business, having formed a rap duo with his friend, the popular beat maker The Alchemist, called The Whooliganz – for which he and The Alchemist went by Mad Skillz and Mudfoot. The Whooliganz canvassed the L.A. rap scene and ended up out on tour with the likes of House of Pain and Cypress Hill, with the duo signing with credible rap hitmakers Tommy Boy Records. But after recording and releasing one single, “Put Your Handz Up,” they saw the their debut album, Make Way for the W shelved in 1994.
At the end of his high school term, Caan did some roadie work with Cypress Hill, but at the urging of his mother, began training in the intensive program of the North Hollywood-based Playhouse West, where his mother was a frequent performer. He began to enjoy the curriculum’s challenges, finding that he enjoyed acting. His father soon tapped him for the title part of the film drama, “A Boy Called Hate” (1995). From there, Caan immediately began landing other parts in modest, independent films, such as Gregg Araki’s surreal L.A. drama, “Nowhere” (1997).
Caan’s resume began to pile up with studio film credits after he was cast as a hitman helping hunt down Will Smith in the Jerry Bruckheimer/Tony Scott thriller, “Enemy of the State” (1998). A year later, in the machismo-laden high school football drama, “Varsity Blues” (1999), Caan displayed his ability to shed his performing inhibitions by appearing in only a cowboy hat, matching the actresses who were supposed to appear in a similar fashion. Caan’s roles began to reflect his forthright sensibility, putting those qualities to maximum effect as the young broker in “Boiler Room” (2000) and as a rabid wrestling fanatic in the Warner Brothers comedy “Ready to Rumble” (2000). The up-and-comer next returned to the world of Bruckheimer, tackling car thievery as a fast-driving car lifter named Tumbler in the misfire, “Gone in Sixty Seconds” (2000).
By 2001, Caan was in the process of getting work from his existing credits. He landed a part in “American Outlaws” (2001), a youth-oriented telling of the Jesse James-Cole Younger gang, with Caan donning yet another cowboy hat to play the brash second banana, Cole Younger. Still, it was the quiet, controlled nature of the performance in “Boiler Room” that attracted writer/director David Atkins, who cast him as Helena Bonham Carter’s menacing brother in the indie thriller “Novocaine” (2001), taking Caan out of car thievery and into the world of drugs, sexual intrigue and seedy blackmail.
While Steven Soderbergh’s Rat Pack update, “Ocean’s Eleven” (2001), was in development in early 2001 – with Caan cast as the wisecracking getaway driver Turk Malloy – the actor was tinkering with a small play which sprung from a year-plus romantic relationship. In the summer of 2001, after “Ocean’s” wrapped and awaited its fall release, Caan returned to Playhouse West to help mount the play, “Almost Love,” a musing on the nature of post-collegiate age love which ran for a week of performances. By 2002, his “Gone in Sixty Seconds” co-star Nicolas Cage had recruited him for his directorial debut “Sonny” (2002), as a former army soldier attempting to recruit the film’s titular gigolo into a more legitimate life.
Having soaked in the process of some top directors, Caan decided to give directing and writing a go himself, churning out “Dallas 362” (2003), a carefully-constructed retro tale of two Los Angeles friends scraping their way across the city’s bars and bar brawls, with Caan playing Dallas, one of the two friends. By the summer of 2004, he was back with the Ocean’s gang for a crooked European vacation in “Ocean’s Twelve” (2004). He was as much intrigued by the bigger films as he was the somewhat smaller ones, and spitting tart-tongued one-liners as the amoral attorney Bryce of the big-budget “Into the Blue” (2005) was followed by a turn in “Friends with Money” (2006), in which he casually managed to both charm and degrade Jennifer Aniston’s educated maid character. 2006 also marked Caan’s return to the director’s chair, with his scripted comedy “The Dog Problem,” a low-key effort about intertwined romantic dog-owners in Los Angeles. Caan turned to the right side of the law as a detective in the ‘30s crime caper “Lonely Hearts” (2006), before Vegas beckoned again, and Turk Malloy was called back to heist duty in the summer smash, “Ocean’s Thirteen” (2007).