1. He has won two Academy Awards, for his roles in the mystery drama Mystic River .
2. Penn began his acting career in television with a brief appearance in a 1974 episode of Little House on the Prairie, directed by his father Leo Penn.
3. He became known as a prominent leading actor with the 1995 drama Dead Man Walking, for which he earned his first Academy Award nomination and the Best Actor Award at the Berlin Film Festival.
4. His fourth feature film, the biographical drama survival movie Into the Wild , garnered critical acclaim and two Academy Award nominations.
5. In addition to his film work, Penn is known for his political and social activism, most notably his criticism of the George W. Bush administration, his contact with the Presidents of Venezuela and Cuba, and his humanitarian work in the aftermath of Hurricane Katrina and the 2010 Haiti earthquake.
6. Penn also attracted media attention for his previous marriages to Madonna and actress Robin Wright.
7. In January 2016, Penn published an interview with Mexican drug lord Joaquín “El Chapo” Guzmán in Rolling Stone.
8. Penn was born in Los Angeles County, California, the son of actor and director Leo Penn and actress Eileen Ryan .
9. His paternal grandparents were Ashkenazi Jewish emigrants from Lithuania and Russia,
10. Penn appeared in a 1974 episode of the Little House on the Prairie television series as an extra when his father, Leo, directed some of the episodes.
11. He launched his film career with the 1981 action-drama Taps, where he played a military high school cadet. The role earned Penn favorable reviews and jump-started his career as a serious actor.
12. In 1985, Penn played Andrew Daulton Lee in the film The Falcon and the Snowman, which closely followed an actual criminal case. Lee was a former drug dealer by trade, convicted of espionage for the Soviet Union and originally sentenced to life in prison, later being paroled in 1998.
13. Nominated for the Academy Award for Best Actor five times, he has won the award twice.
14. The Academy first recognized his work in nominating him for playing a racist murderer on death row in the 1995 drama film Dead Man Walking.
15. He was nominated again for his comedic performance as an egotistical jazz guitarist in the 1999 film Sweet and Lowdown.
16. Penn finally won for his role in the 2003 Boston crime-drama Mystic River.
17. In 2004, he played Sam Byck, who in 1974 attempted and failed to assassinate President Richard Nixon, in The Assassination of Richard Nixon.