Caan was a
roadie for the
hip hop groups
Cypress Hill and
House of Pain. Caan was also a member of the hip hop duo
The Whooliganz as Mad Skillz (with
producer and fellow
MC The Alchemist as Mudfoot). The Whooliganz signed a record deal with Tommy Boy/Warner Bros. records and recorded the album
Make Way for the W, but after their first single "Put Your Handz Up" was released 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 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. His first role in a major motion picture was that of Charlie Tweeder, a reckless
philandering Texas high school football wide receiver in the
teen movie Varsity Blues (1999), alongside
James Van Der Beek and
Paul Walker. 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 won a prize at the 2003 Las Vegas Film Festival. 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 had appeared in Varsity Blues
) in the action film Into the Blue. 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. Caan played Detective
Danny "Danno" Williams in
Hawaii Five-0 (a re-imagining of the 1968
Hawaii Five-O television series). The new series premiered on September 20, 2010, and in 2011 he was nominated for a
Golden Globe Award for Best Supporting Actor – Series, Miniseries or Television Film for his performance.
BuddyTV ranked him 95th on its list of "TV's Sexiest Men of 2011". In addition to acting, Caan has also pursued a career in photography. Inspired and trained by cinematographer
Phil Parmet while working together on the 2003 film
Dallas 362, Caan has been shooting ever since. "In preparing for the film," Caan said, "Phil inspired me to learn about lenses, lights, frames, and the operation of a 250 millimeter camera. By the time the film was over, I wanted to shoot the next one." In 2009, he published his first collection of photographs in a 256-page book titled
Scott Caan Photographs, Vol. 1. The book was edited and designed by
Howard Nourmand, and includes an introduction by
Steve Olson. ==Personal life==