The 12th Chicago Film Critics Association Awards, given on 13 March 2000, honored the finest achievements in 1999 filmmaking.

• 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

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