Born March 26, 1939, in the Bronx, NY, Caan decided to pursue a career in acting while attending college and in 1960 was accepted by Sanford Meisner into the Neighborhood Playhouse. After making his debut off-Broadway in I Roam, he landed in the Broadway production of Mandingo but exited after just four performances because of artistic difficulties with star Franchot Tone. Caan then landed in television, where he became a busy character actor; he made his film debut in an unbilled performance in 1963's Irma La Douce, followed by a meatier role in Lady in a Cage the following year. The 1965 Howard Hawks auto-racing drama Red Line 7000 was his first starring role, followed two years later by the Hawks Western El Dorado, which cast him opposite John Wayne and Robert Mitchum; in 1968, Caan starred in Robert Altman's Countdown, and in 1969, he appeared in Francis Ford Coppola's The Rain People.

Caan shot to fame thanks to a poignant performance in the 1970 television movie Brian's Song, in which he played the ill-fated Chicago Bears star Brian Piccolo; his turn as the similarly ill-fated Sonny Corleone in Coppola's 1972 masterpiece The Godfather solidified his stardom and earned him an Academy Award nomination, but his subsequent films, including 1973's Slither and the next year's Freebie and the Bean, failed to live up to expectations. After earning a Golden Globe bid for his work in 1974's The Gambler, Caan briefly appeared in 1974's The Godfather Pt. 2 before co-starring with Barbra Streisand in the hit Funny Lady, followed by Norman Jewison's futuristic parable Rollerball. When both 1975's Sam Peckinpah thriller The Killer Elite and 1976's Harry and Walter Go to New York met with failure, Caan's career took a downward turn, and apart from cameo appearances in both Mel Brooks' Silent Movie and the star-studded A Bridge Too Far, he was largely absent from screens for a time. He also made any number of ill-considered decisions; he and Coppola were unable to come to terms for Apocalypse Now, and he also rejected roles in hits including One Flew Over the Cuckoo's Nest, Superman, and Kramer vs. Kramer.

By the end of the decade, Caan's career had hit the skids, as projects including the 1978 Western Comes a Horseman (co-starring Jane Fonda) and the following year's Neil Simon drama Chapter Two all failed to live up to expectations. His directorial debut in 1980's Hide in Plain Sight fared no better, although Michael Mann's thriller Thief garnered a cult following; when 1982's Kiss Me Goodbye bombed, Caan disappeared from sight for the next five years. Finally, in 1987, Caan resurfaced, starring in Coppola's war drama Gardens of Stone; the next year's science fiction picture Alien Nation was a hit, as was his next major project, Rob Reiner's 1990 feature Misery. After 1991's For the Boys failed to connect with audiences, Caan spent much of the decade in prominent supporting roles which showcased his smart, edgy persona; among the more high-profile were 1992's Honeymoon in Vegas, 1996's Eraser, and the wonderful indie hit Bottle Rocket.

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