Academy of Motion Picture Arts and Sciences
| Nominated | Best Director | 1999 |
| Nominated | Best Original Screenplay | 1999 |
| Nominated | Best Supporting Actress | 1999 |
British Academy of Film and Television Arts
| Nominated | Best Editing | 1999 |
| Won | Best Original Screenplay | 1999 |
| Nominated | Best Supporting Actress | 1999 |
Broadcast Film Critics Association
| Won | Breakthrough Performer | 1999 |
Chicago Film Critics Association
| Won | Best Screenplay | 1999 |
Deauville Film Festival
| Won |
American Independent Film Grand Prize |
1999 |
Directors Guild of America
| Nominated | Best Director - Feature Film | 1999 |
French Academy of Cinema
| Nominated |
Best Foreign Language Film |
1999 |
Hollywood Foreign Press Association
| Nominated |
Best Picture - Musical or Comedy |
1999 |
| Nominated | Best Screenplay | 1999 |
| Nominated | Best Supporting Actress in a Series, Miniseries or Motion Picture Made for Television | 1999 |
Independent Spirit Awards
| Nominated | Best Actor | 1999 |
| Won | Best First Feature Over $500,000 | 1999 |
| Won | Best First Screenplay | 1999 |
Los Angeles Film Critics Association
| Won | Best Screenplay | 1999 |
National Board of Review
| Nominated |
Best Picture |
1999 |
National Society of Film Critics
| Won |
Best Picture |
1999 |
| Won | Best Screenplay | 1999 |
New York Film Critics Circle
| Won | Best First Film | 1999 |
| Won | Best Supporting Actor | 1999 |
| Won | Best Supporting Actress | 1999 |
Screen Actors Guild
| Nominated | Best Female Actor in a Supporting Role | 1999 |
| Nominated |
Best Performance by a Cast |
1999 |
Toronto Film Critics Association
| Won |
Best Picture [Runner-up] |
1999 |
| Won | Best Screenplay | 1999 |
Writers Guild of America
| Nominated | Best Original Screenplay | 1999 |
