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
