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Academy Awards

2000 | Nominee: Best Writing, Screenplay Based on Material Previously Produced or Published

Independent Spirit Awards

2000 | Winner: Best Feature

Independent Spirit Awards

2000 | Winner: Best Director

Independent Spirit Awards

2000 | Winner: Best Screenplay

Independent Spirit Awards

2000 | Nominee: Best Debut Performance

Independent Spirit Awards

2000 | Nominee: Best Female Lead

Village Voice Film Poll

1999 | Nominee: Best Film

National Board of Review

1999 | Winner: Special Recognition

Writers Guild of America

2000 | Winner: Best Screenplay Based on Material Previously Produced or Published (Screen)

Golden Globes (USA)

2000 | Nominee: Best Performance by an Actress in a Motion Picture - Comedy or Musical

New York Film Critics Circle Awards

1999 | Winner: Best Screenplay

Los Angeles Film Critics Association Awards

1999 | Winner: New Generation Award

Los Angeles Film Critics Association Awards

1999 | 2nd place: Best Actress

National Society of Film Critics Awards

2000 | Winner: Best Actress

National Society of Film Critics Awards

2000 | 2nd place: Best Screenplay

National Society of Film Critics Awards

2000 | 3rd place: Best Film

Chicago Film Critics Association Awards

2000 | Nominee: Best Actress

Boston Society of Film Critics Awards

1999 | 2nd place: Best Screenplay

Valladolid International Film Festival

1999 | Winner: Best New Director

American Comedy Awards

2000 | Nominee: Funniest Actress in a Motion Picture (Leading Role)