(*): W=Win, N=Nomination
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1998 | N | Most Promising Actor | Rushmore (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2000 | N | Best Actor | Rushmore (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2012 | N | - | Moonrise Kingdom (2012) | Bruce Willis, Edward Norton, Bill Murray |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1999 | W | Best Actor | Rushmore (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2005 | N | Outstanding Actor in a Supporting Role, Comedy or Musical | Shopgirl (2005) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2011 | N | Best Villain | Scott Pilgrim vs. the World (2010) | Brandon Routh, Chris Evans, Mae Whitman |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2015 | N | Outstanding Performance by a Cast in a Motion Picture | The Grand Budapest Hotel (2014) | Adrien Brody, Ralph Fiennes, Harvey Keitel |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1999 | N | Film - Choice Hissy Fit | Rushmore (1998) | - |
| 1999 | N | Film - Breakout Performance | Rushmore (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1999 | W | Best Performance by a Young Actor in a Comedy Film | Rushmore (1998) | - |
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