50 interesting facts about Sean Penn: His anti-war stance and who he's dated

Sean Justin Penn is an American actor. He has won two Academy Awards, for his roles in Mystic River and Milk.

1. His full name is Sean Justin Penn.
2. He was born on August 17, 1960 in Los Angeles County, California, United States. He has the same birthday as Robert De Niro.
3. Sean Penn was born into a household of actors. His father is actor and director Leo Penn and his mother is actress Eileen Ryan.
4. His paternal grandparents were Jewish emigrants from Lithuania and Russia, while his mother is a Catholic of Irish and Italian descent.
5. His grandparents established a Jewish deli in New York.
6. 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.
7. Penn began making short films with some of his childhood friends, including actors Emilio Estevez and Charlie Sheen, who lived near his home.
8. In 1981, he made his film debut alongside budding star Tom Cruise and Academy Award winner Timothy Hutton in the military school drama Taps.
9. His breakout role came in 1982, when he played Jeff Spicoli, the stoner surfer, in Fast Times at Ridgemont High.
10. In 1983, Penn appeared as Mick O'Brien, a troubled youth, in the drama Bad Boys. The role earned Penn favorable reviews and jump-started his career as a serious actor.
11. In 1986 Sean Penn appeared in the movie "At Close Range". His brother Chris Penn and mother Eileen Ryan also appeared in the film. His mother played his grandmother.
12. Penn there was in the same acting class as Michelle Pfeiffer at the end of the 70s or early 80s.
13. He married pop star and actress Madonna in 1985. One of the guests at their wedding was artist Andy Warhol.
14. He starred together with his then wife, Madonna, in "Shanghai Surprise" in 1986.
15. In 1987, Penn spent 32 days in jail after hitting an extra.
16. Sean Penn and Maddona's marriage ended in 1989.
17. Penn had another run in with the law with an attempted murder rap in Macao in 1986, after he allegedly hung a paparazzo off a ninth-floor balcony - an act he was finally pardoned for after escaping from the country by jetfoil.
18. In 1991, two years after earning rave reviews for his performance in Casualties of War (1989), Penn directed his first film. The feature The Indian Runner opened to a limited release in theaters, and made a meager $34,047 at the box office. Critics gave the film mild praise.
19. He established a production company named Clyde Is Hungry Productions.
20. He began a relationship with actress Robin Wright, with whom they have two children, a daughter named Dylan Francis, born in 1991, and a son named Hopper Jack, born in 1993.
    
21. He lost his home in Malibu due to a fire in November 1993.
22. Though he previously claimed he quit acting, Penn returned to the front of the camera in 1993, playing a coke-addled criminal lawyer in De Palma's Carlito's Way, co-starring Al Pacino. His performance earned him a Golden Globe nomination for best supporting actor.
23. Sean Penn and Robing Wright got married on April 27, 1996.
24. Penn elected to move to Marin County which is located north of San Francisco. He cited that he made the move so that he didn't have to raise his children within the Hollywood system.
25. He directed Jewel's music video, "You Were Meant For Me," in 1997.
26. In 2002, Penn starred opposite Michelle Pfeiffer in I Am Sam, playing a mentally disabled man who fights to regain custody of his young daughter.
27. Sean Penn and Robin Wright had a volatile relationship. They first filed for divorce in December 2007, but reconciled several months later, requesting a court dismissal of their divorce case.
28. Later in April 2009, Penn filed for legal separation, only to withdraw the case once again when the couple reconciled in May. On August 12, 2009, Robin Wright Penn filed for divorce again.
29. In September 2005, Penn traveled to New Orleans, Louisiana to aid Hurricane Katrina victims. He was physically involved in rescuing people, although there was criticism that his involvement was a PR stunt as he hired a photographer to come along with his entourage. Penn denied such accusations in an article he wrote for The Huffington Post.
30. Sean Penn partially owns a Parisian restaurant-bar named Man Ray alongside Johnny Depp and Mick Hucknall.
31. He and director Clint Eastwood discussed the possibility of Sean starring in Blood Work (2002). Though it didn't work out, they got the opportunity to work together later in Mystic River (2003).
32. In 2002 Sean Penn took out an entire page in the Washington Post as he wished to publish an open letter on the page to President George W. Bush. The letter was in regards to the war.
33. As of 2005, the only actor to ever receive a Best Actor nomination for a Woody Allen film, besides Allen himself.
34. The longest he has gone without an Oscar nomination if 5 years, between Mystic River (2003) and Milk (2008).
35. Penn visited Iran in June 2005 under the disguise of a journalist on an assignment for the San Francisco Chronicle and even attended Friday prayer ceremony at Tehran University.
36. His car, a limited-edition 1987 Buick Grand National, was stolen in Berkeley months after his return from Iraq. Among the lost contents were 2 guns.
37.  In October 2008, Penn traveled to Cuba, where he met with and interviewed President Raúl Castro.
38. In February 2012, he stood beside Hugo Chávez while Venezuela supported the Syrian government during the 2011-2012 Syrian uprising.
39. In March 2010, Penn called for the arrest of those referring to Venezuelan President Hugo Chávez as a dictator. The two were friends, and when Chávez died, Penn said: "Venezuela and its revolution will endure under the proven leadership of Vice President (Nicolás) Maduro. Today the United States lost a friend it never knew it had. And poor people around the world lost a champion. I lost a friend I was blessed to have."
40. After the 2010 Haiti earthquake, Penn founded the J/P Haitian Relief Organization,[44] which has been running a 55,000 person tent camp.
    
41. He claims to smoke four packs of cigarettes a day. He quit smoking at age 40 due to health concerns but that did not last long and he picked the habit back up.
42. Penn dislikes the paparazzi. He dislikes them quite a bit. After scuffling with one at his Reservoir Dog brother Chris' funeral in 2006, he explained: "They're the dung beetles of the world. They reek of piss."
43. His name inspired an indie-band in The Netherlands to call their group as Seanpenn.
44. Penn has also dated actresses Elizabeth McGovern and Susan Sarandon - since married to his Mystic River co-star Tim Robbins - as well as singer Jewel and supermodel Petra Nemcova.
45. Penn is currently dating Oscar-winning actress Charlize Theron.
    
46. He is an avid surfer.
47. Sean Penn is the 9th person to win two Academy Awards for Best Actor.
48. As of 2014, has appeared in four films that were nominated for the Best Picture Oscar: The Thin Red Line (1998), Mystic River (2003), Milk (2008) and The Tree of Life (2011).
49. He dedicated his film, The Crossing Guard, to Charles Bukowski.
50. Sean Penn's net worth is $150 million.