Sean Penn was in romantic comedy films.
Sean Penn . He has won two Academy Awards , for his roles in the mystery drama Mystic River ( 2003 ) and the biopic Milk ( 2008 ) . Following his film debut in the drama Taps ( 1981 ) and a diverse range of film roles in the 1980s , including Fast Times at Ridgemont High ( 1982 ) , Penn garnered critical attention for his roles in the crime dramas At Close Range ( 1986 ) , State of Grace ( 1990 ) , and Carlito 's Way ( 1993 ) . Penn received another two Oscar nominations for Woody Allen 's comedy-drama Sweet and Lowdown ( 1999 ) and the drama I Am Sam ( 2001 ) , before winning his first Academy Award for Best Actor in 2003 for Mystic River and a second one in 2008 for Milk . His fourth feature film , the biographical drama survival movie Into the Wild ( 2007 ) , garnered critical acclaim and two Academy Award nominations .