| Mystic River, Milk, and Gangster Squad actor (4,4) |
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| Who won his first Academy Award for Best Actor in the film Mystic River (2003) |
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| "Milk" star (2 wds.) |
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| Best Actor in a Leading Role Oscar winner for Milk (4,4) |
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| Actor, director and activist who won Oscars for his roles in Mystic River and Milk (4,4) |
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| He won Oscars forMystic River and Milk (4,4) |
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| Childhood pal of Charlie Sheen |
Newsday |
25 Feb 2023 |
| Two time Academy Award winning actor of "Mystic River" who appeared in a guest role on "Two and a Half Men": 2 wds. |
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| ____ won Oscars for his roles in Mystic River and Milk |
The Times Specialist Sunday |
14 Apr 2019 |
| Actor famous for "Milk" and "Mystic River" who appeared as a guest star on "Friends": 2 wds. |
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| 'Milk' star, 2008 |
New York Times |
05 Nov 2017 |
| "Milk" star, 2008 |
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| Co-screenwriter and star of "The Gunman" |
LA Times Daily |
13 Jan 2016 |
| Co-screenwriter and star of "The Gunman" |
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| 'Milk' man |
New York Times |
09 Jan 2015 |
| "Milk" man |
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| "Milk" star |
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| Oscar winner for "Mystic River" and "Milk" |
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| 2008 Harvey Milk portrayer |
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| 2008 Harvey Milk portrayer |
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| "Mystic River" costar |
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| "Mystic River" costar |
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| Best Actor of 2003 |
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| "Mystic River" co-star, 2003 |
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| Prison worker, perhaps |
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| Madonna's ex |
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| Star of "Dead Man Walking" |
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| He played himself in "Being John Malkovich" |
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| He played himself in "Being John Malkovich" |
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| "Sweet and Lowdown" star |
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| Robin Wright's husband |
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