The 5th Critics' Choice Awards were presented on January 24, 2000, honoring the finest achievements of 1999 filmmaking.^[1][2]

(in alphabetical order)

• American Beauty
• Being John Malkovich
• The Cider House Rules
• The Green Mile
• The Insider
• Magnolia
• Man on the Moon
• The Sixth Sense
• The Talented Mr. Ripley
• Three Kings

• Best Actor:
  • Russell Crowe – The Insider
• Best Actress:
  • Hilary Swank – Boys Don't Cry
• Best Animated Feature:
  • Toy Story 2
• Best Child Performer:
  • Haley Joel Osment – The Sixth Sense
• Best Composer:
  • Gabriel Yared – The Talented Mr. Ripley
• Best Director:
  • Sam Mendes – American Beauty
• Best Family Film:
  • October Sky
• Best Feature Documentary:
  • Buena Vista Social Club
• Best Foreign Language Film:
  • All About My Mother (Todo sobre mi madre) • Spain
• Best Picture:
  • American Beauty
• Best Picture Made For Television:
  • RKO 281 / Tuesdays with Morrie (TIE)
• Best Screenplay – Adapted:
  • The Green Mile – Frank Darabont
• Best Screenplay – Original:
  • American Beauty – Alan Ball
• Best Song:
  • "Music of My Heart" – Music of the Heart
• Best Supporting Actor:
  • Michael Clarke Duncan – The Green Mile
• Best Supporting Actress:
  • Angelina Jolie – Girl, Interrupted
• Breakthrough Performer:
  • Spike Jonze – Being John Malkovich and Three Kings