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Matt Dillon

Once typecast as a doomed young rebel with smoldering good looks, Oscar-nominee Matt Dillon managed to outlast his teen stardom from Francis Ford Coppola's "The Outsiders" (1983) and enjoy a respected career in both drama and comedy. His acclaimed starring role in Gus Van Sant's "Drugstore Cowboy" (1989) helped build a bridge from Dillon's reckless teen roles to more adult fare, though he showed a career-long penchant for seedy and duplicitous characters, to which he always brought a charismatic charm or brooding allure. While making successful forays into cartoonish, blockbuster comedies like "There's Something About Mary" (1998) and "You, Me and Dupree" (2007), Dillon also stuck close to independent film where he displayed uncommon versatility with Ted Demme's "Beautiful Girls" (1996), "Factotum" (2006), and Paul Haggis' "Crash" (2005), for which he won an Independent Spirit Award for Best Supporting Actor. Despite the New Yorker's Hollywood-outsider status, Dillon maintained a prolific career that steadily held the respect of critics and audiences for several decades.