- Son of formerly blacklisted director Leo Penn
- Jailed 32 days in 1987 for hitting an extra
- Directed video for Jewel's "You Were Meant for Me"
- Once gave Madonna half of a heart pendant. Recently buried the other half in Area 51
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Win:
Best Actor, Academy Awards
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Win:
Best Actor, Screen Actors' Guild
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Win:
Best Actor, Boston Film Critics
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Win:
Best Actor, New York Film Critics
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Win:
Best Actor, Los Angeles Film Critics
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Win:
Best Actor, National Society of Film Critics
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Win:
Best Actor, Broadcast Film Critics Association
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Win:
Best Actor, Southeastern Film Critics Association
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Win:
Best Actor, Dallas Fort Worth Critics
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Nominee:
Best Actor, Spirit Awards
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Runner-Up:
Best Actor, Online Film Critics Association
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Nominee:
Best Actor, Chicago Film Critics
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Nominee:
Best Actor - Drama, Golden Globes
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Runner-up:
Best Actor - Drama, Golden Satellites
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Win:
Best Actor, Academy Awards
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Win:
Best Actor, National Board of Review
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Win:
Best Actor - Drama, Golden Globes
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Win:
Best Actor, Broadcast Film Critics Association
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Win:
Best Actor, Las Vegas Film Critics
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Win:
Best Actor, Florida Film Critics
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Win:
Best Actor, Kansas City Film Critics
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Win:
Best Actor, Dallas Fort Worth Critics
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Runner-Up:
Best Actor, Washington (DC) Area Film Critics Association
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Runner-Up:
Best Actor - Drama, Golden Satellites
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Runner-up:
Best Actor, BOP's Calvin Awards
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Runner-Up:
Best Actor, National Society of Film Critics
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Runner-Up:
Best Actor, Boston Film Critics
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Runner-Up:
Best Actor, Online Film Critics Association
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Runner-Up:
Best Actor, Chicago Film Critics
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Runner-Up:
Best Actor, Screen Actors' Guild
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Nominee:
Best Actor, London Film Critics
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Runner-Up:
Best Actor, Southeastern Film Critics Association
View other Big Pictures
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