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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 has since directed three more films, all well received by critics: the indie thriller The Crossing Guard (1995), the mystery film The Pledge (2001), and the biographical drama survival film Into the Wild (2007). The two starred in the panned and much-derided Shanghai Surprise (1986), directed by Jim Goddard, and Madonna dedicated her third studio album True Blue (1986) to Penn, referring to him in the liner notes as "the coolest guy in the universe".
Lee was a former drug dealer by trade, convicted of espionage for the Soviet Union and originally sentenced to life in prison, but was paroled in 1998.
The same year, he was invited to join the Academy of Motion Picture Arts and Sciences.
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).
He has won two Academy Awards, for his roles in the mystery drama Mystic River (2003) and the biopic Milk (2008).
Penn began his acting career in television with a brief appearance in episode 112 of Little House on the Prairie (December 4, 1974), directed by his father Leo Penn.