He received his third Oscar nomination for the role.
The following year, he starred in Clint Eastwood's small town drama (2013), a movie about the clash between law enforcement and organized crime in Los Angeles in the 1940s and 1950s.
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Madonna auctioned off a variety of personal items, raising more than $7.5 million in the process, and managed to rope in her ex-husband Penn to part with some cash for a good cause.
When the singer's Swarovski crystal-covered dress by Jeremy Scott for Moschino from her Rebel Heart Tour came up for sale, Penn was locked in a bidding war with pop star Ariana Grande, who modelled the dress onstage and kissed Madonna after the pair danced together.
Actor Sean Justin Penn was born on August 17, 1960, in Santa Monica, California. An interest in filmmaking, specifically directing, led to Penn's passion for acting, which included several early TV parts.
He moved to New York City at the age of 19 and soon landed a part in a Broadway play, , and a barrage of tabloid headlines.
"I’m still in love with you,” Madonna told her ex-husband, and said she would marry him again but only if he bid $150,000 for the dress.
The Oscar-winning actor did just that, and went on to win the dress for 0,000.
It was also unclear whether the actor was facing legal problems for his involvement in the situation.
star Robin Wright wed in 1996 and have two children.
Warner Brothers, the studio behind's website on January 9, 2016, Penn revealed that he had met with Mexican drug kingpin Joaquín "El Chapo" Guzmán at an undisclosed location in October 2015.
Guzmán, who had orchestrated a daring escape from a high-security prison three months earlier, was looking to have a movie made about his life, and had agreed to an interview through Penn's contact with Mexican actress Kate del Castillo.
The couple divorced in 2010 in a non-amicable split.