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| 2000 |
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Space Cowboys is released. |
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Wins Career Golden Lion at the Venice Film Festival. |
| 2003 |
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Directs Mystic River, which wins numerous awards and accolades, including Academy Awards for two of its stars, Sean Penn and Tim Robbins. |
| 2004 |
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Directs and stars in Million Dollar Baby, acclaimed by many as one of the best pictures of the year. |
| 2005 |
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Million Dollar Baby wins 4 Academy Awards, including Best Picture and Director! |
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