Chicago Film Critics Association Awards 1999

Source:^[1]

• Best Actor:
  • Kevin Spacey - American Beauty
• Best Actress:
  • Hilary Swank - Boys Don't Cry
• Best Cinematography:
  • Snow Falling on Cedars - Robert Richardson
• Best Director:
  • Sam Mendes - American Beauty
• Best Film:
  • American Beauty
• Best Foreign Language Film:
  • Todo sobre mi madre (All About My Mother), Spain
• Best Score:
  • "South Park: Bigger, Longer & Uncut"- Trey Parker and Marc Shaiman
• Best Screenplay:
  • Being John Malkovich - Charlie Kaufman
• Best Supporting Actor:
  • Tom Cruise - Magnolia
• Best Supporting Actress:
  • Chloë Sevigny - Boys Don't Cry
• Most Promising Actor:
  • Wes Bentley - American Beauty
• Most Promising Actress (tie):
  • Émilie Dequenne - Rosetta
  • Julia Stiles - 10 Things I Hate About You
• Commitment to Chicago Award
  • The Cusack Family: Dick, Nancy, Joan, Susan, Ann, John, and Bill
• Big Shoulders Awards
  • Facets Multi-Media, Inc.