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He stars as Detective Danny "Danno" Williams in the CBS television series Hawaii Five-0 (2010–present), for which he was nominated for a Golden Globe Award.
Caan had a recurring role as manager Scott Lavin in the HBO television series Entourage (2009–2011).
Caan reunited with his former partner The Alchemist in 2014 on the Step Brothers project Lord Steppington, performing on the song "Byron G" with musician Evidence.
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.
For his signature role in The Godfather (1972), that of hot-tempered Sonny Corleone, Caan was nominated for the Academy Award for Best Supporting Actor and the corresponding Golden Globe.
The Alchemist and he, when performing as the rap duo the Whooliganz in the early 1990s, signed a record deal with Tommy Boy/Warner Bros. 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 was a roadie for the hip hop 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).