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Mexican authorities dismissed the level of importance given by American media to Penn in regard to Guzman's eventual recapture, instead placing importance on actress Kate del Castillo's continued communications with Guzman.
He also directed music videos, such as Shania Twain's "Dance with the One That Brought You" (1993), Lyle Lovett's "North Dakota" (1993), and Peter Gabriel's "The Barry Williams Show" (2002).
He received his third nomination after portraying a mentally handicapped father in I am Sam (2001).
Penn finally won for his role in the Boston crime-drama Mystic River (2003).
In November 2008, Penn earned positive reviews for his portrayal of real-life gay-rights icon and politician Harvey Milk in the biopic Milk (2008), and was nominated for best actor for the 2008 Independent Spirit Awards.
The film also earned Penn his fifth nomination and second win for the Academy Award for Best Actor. Wilson in Fair Game (2010), a film adaptation of Valerie Plame's 2007 memoir.
Next, Penn portrayed governor Willie Stark (based on Huey Long) in an adaptation of Robert Penn Warren's classic 1946 American novel All the King's Men (2006).