Sean Penn won the Academy Awards (Oscars) for Best Actor twice (2004, 2009). Sean Penn won the Golden Globe Awards for Best Actor in a Motion Picture – Drama in 2004 for Mystic River.
| Year | Contest | Category | For | Sources |
|---|---|---|---|---|
| 2009 | Academy Awards (Oscars) | Best Actor | Milk | 1 · 2 |
| 2004 | Academy Awards (Oscars) | Best Actor | Mystic River | 1 · 2 |
| 2004 | Golden Globe Awards | Best Actor in a Motion Picture – Drama | Mystic River | 1 · 2 |