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The film was a critical and commercial failure, named by a 2010 Forbes article as the biggest flop in the last five years.
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.
In January 2016, Penn published an interview (conducted in October 2015) with Mexican drug lord Joaquín "El Chapo" Guzmán in Rolling Stone.
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 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".
The relationship was marred by violent outbursts against the press, including one incident when Penn was arrested for assaulting a photographer on a film set; Penn was sentenced to 60 days in jail in mid-1987, of which he served 33 days.
but later withdrew the papers, only to file them again in January 1989.
In 2004, Penn played Samuel Bicke, a character based on Samuel Byck, who in 1974 attempted and failed to assassinate President Richard Nixon, in The Assassination of Richard Nixon (2004).
Penn launched his film career with the action-drama Taps (1981), where he played a military high school cadet.
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.
In 2015, Penn starred in The Gunman, a French-American action thriller based on the novel The Prone Gunman, by Jean-Patrick Manchette.
Jasmine Trinca, Idris Elba, Ray Winstone, Mark Rylance and fellow Oscar-winner Javier Bardem appear in supporting roles.