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Sean Penn movies: 15 greatest films, ranked worst to best, include ‘Dead Man Walking,’ ‘Mystic River,’ ‘Milk’

Sean Penn movies: 15 greatest films, ranked worst to best, include ‘Dead Man Walking,’ ‘Mystic River,’ ‘Milk’

Sean Penn celebrates his 59th birthday on August 17, 2019. The two-time Oscar winner has excelled in a number of fields, including acting, writing and directing. But it’s his career as a performer that has brought him the most acclaim. In honor of his birthday, let’s take a look back at 15 of his greatest films as an actor, ranked worst to best.

Penn entered the Oscar race for the first time with his performance as a death row inmate in Tim Robbins’s “Dead Man Walking” (1995), for which he competed in Best Actor. Subsequent lead nominations as a jazz guitarist in Woody Allen’s “Sweet and Lowdown” (1999) and a mentally handicapped father in “I Am Sam” (2001) quickly followed.

SEEWoody Allen movies: Top 25 greatest films ranked worst to best

He hit the Oscar jackpot with Clint Eastwood’s “Mystic River” (2003), which cast him as a criminal grieving the murder of his daughter.

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