Penn directed one of the 11 segments of 11'09"01 September 11 (2002), a compilation film made in response to the September 11 attacks.His fourth feature film, the biographical drama survival movie Into the Wild (2007), garnered critical acclaim and two Academy Award nominations.He was nominated again for his comedic performance as an egotistical jazz guitarist in the film Sweet and Lowdown (1999).
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".
Penn later hired Lee as his personal assistant, partly because he wanted to reward Lee for allowing him to play Lee in the film; Penn was also a firm believer in rehabilitation and thought Lee should be successfully reintegrated into society, since he was a free man again.
The Academy Awards first recognized his work in nominating him for playing a racist murderer on death row in the drama film Dead Man Walking (1995).
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).Madonna reportedly filed an assault complaint that she was beaten in her Malibu home by her estranged husband, but in January 1989, the Associated Press reported that she had "dropped assault charges." Penn and Wright separated in 1995, during which time he developed a relationship with Jewel, after he spotted her performing on Late Night with Conan O'Brien.He invited her to compose a song for his film The Crossing Guard (1995) and followed her on tour.is an American actor, filmmaker, and political activist.He has won two Academy Awards, for his roles in the mystery drama Mystic River (2003) and the biopic Milk (2008).In January 2016, Penn published an interview (conducted in October 2015) with Mexican drug lord Joaquín "El Chapo" Guzmán in Rolling Stone.