Academy Awards
| Year | Award | Category | Cast & Crew | Result |
|---|---|---|---|---|
| 1999 | Academy of Motion Picture Arts and Sciences | Best Original Screenplay | Paul Thomas Anderson | Nominated |
| 1999 | Academy of Motion Picture Arts and Sciences | Best Supporting Actor | Tom Cruise | Nominated |
| 1999 | Academy of Motion Picture Arts and Sciences | Best Original Song | Aimee Mann | Nominated |
Berlin International Film Festival
| Year | Award | Category | Cast & Crew | Result |
|---|---|---|---|---|
| 2000 | Berlin International Film Festival | Golden Bear | Won |
Chicago Film Critics Association
| Year | Award | Category | Cast & Crew | Result |
|---|---|---|---|---|
| 1999 | Chicago Film Critics Association | Best Supporting Actor | Tom Cruise | Won |
Golden Globes
| Year | Award | Category | Cast & Crew | Result |
|---|---|---|---|---|
| 1999 | Hollywood Foreign Press Association | Best Performance by an Actor in a Motion Picture | Tom Cruise | Won |
| 1999 | Hollywood Foreign Press Association | Best Original Song | Aimee Mann | Nominated |
National Board of Review
| Year | Award | Category | Cast & Crew | Result |
|---|---|---|---|---|
| 1999 | National Board of Review | Best Ensemble Acting | Won | |
| 1999 | National Board of Review | Best Supporting Actor | Philip Seymour Hoffman | Won |
| 1999 | National Board of Review | Best Supporting Actress | Julianne Moore | Won |
| 1999 | National Board of Review | Best Picture | Nominated |
National Society of Film Critics
| Year | Award | Category | Cast & Crew | Result |
|---|---|---|---|---|
| 1999 | National Society of Film Critics | Best Supporting Actor (Runner-up) | Philip Seymour Hoffman | Won |
| 1999 | National Society of Film Critics | Best Supporting Actress (Runner-up) | Julianne Moore | Won |
Screen Actors Guild Awards
| Year | Award | Category | Cast & Crew | Result |
|---|---|---|---|---|
| 1999 | Screen Actors Guild | Best Female Actor in a Supporting Role | Julianne Moore | Nominated |
| 1999 | Screen Actors Guild | Best Supporting Actor | Tom Cruise | Nominated |
| 1999 | Screen Actors Guild | Best Performance by a Cast | Nominated |
Toronto Film Critics Association
| Year | Award | Category | Cast & Crew | Result |
|---|---|---|---|---|
| 1999 | Toronto Film Critics Association | Best Picture | Won | |
| 1999 | Toronto Film Critics Association | Best Screenplay | Paul Thomas Anderson | Won |
| 1999 | Toronto Film Critics Association | Best Director | Paul Thomas Anderson | Won |
Writers Guild of America
| Year | Award | Category | Cast & Crew | Result |
|---|---|---|---|---|
| 1999 | Writers Guild of America | Best Original Screenplay | Paul Thomas Anderson | Nominated |

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