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He was also seen in episodes of Play of the Week, Route 66, Alcoa Premiere, The Untouchables (in an episode guest starring Lee Marvin), The Doctors and the Nurses, Wide Country, Death Valley Days (twice) and Dr. Caan's first film was Irma la Douce (1963), in which he had an uncredited bit as a sailor. (playing a German soldier), and Kraft Suspense Theatre.
His first substantial film role was as a punk hoodlum in the 1964 thriller Lady in a Cage, which starred Olivia de Havilland, who praised Caan's performance.
For his contributions to the film industry, Caan was inducted into the Hollywood Walk of Fame in 1978 with a motion pictures star located at 6648 Hollywood Boulevard.
He was educated in New York City, and later attended Michigan State University.
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 plays Detective Danny "Danno" Williams in Hawaii Five-0 (a re-imagining of the 1968 Hawaii Five-O television series).
Caan was also a member of the hip-hop group The Whooliganz as Mad Skillz (with producer and fellow MC The Alchemist as Mudfoot).Caan had roles in The Alfred Hitchcock Hour and Wagon Train.He was fourth-billed in a Western feature, The Glory Guys (1965).In the 1990s, he was a part of hip hop group The Whooliganz with The Alchemist.The duo went by the names Mad Skillz and Mudfoot, respectively.