The 25th Los Angeles Film Critics Association Awards, honoring the best in film for 1999, were announced on December 11, 1999 and awarded on January 19, 2000.^[1][2]

• Best Picture:
  • The Insider
  • Runner-up: American Beauty
• Best Director:
  • Sam Mendes – American Beauty
  • Runner-up: Michael Mann – The Insider
• Best Actor:
  • Russell Crowe – The Insider
  • Runner-up: Richard Farnsworth – The Straight Story
• Best Actress:
  • Hilary Swank – Boys Don't Cry
  • Runner-up: Reese Witherspoon – Election
• Best Supporting Actor:
  • Christopher Plummer – The Insider
  • Runner-up: John Malkovich – Being John Malkovich
• Best Supporting Actress:
  • Chloë Sevigny – Boys Don't Cry
  • Runner-up: Samantha Morton – Sweet and Lowdown
• Best Screenplay:
  • Charlie Kaufman – Being John Malkovich
  • Runner-up: Alan Ball – American Beauty
• Best Cinematography:
  • Dante Spinotti – The Insider
  • Runner-up: Conrad L. Hall – American Beauty
• Best Production Design:
  • Rick Heinrichs – Sleepy Hollow
  • Runner-up: Dante Ferretti – Titus
• Best Music Score:
  • Trey Parker and Marc Shaiman – South Park: Bigger, Longer & Uncut
  • Runner-up: Gabriel Yared – The Talented Mr. Ripley
• Best Foreign-Language Film:
  • All About My Mother (Todo sobre mi madre) • Spain
  • Runner-up: The Dreamlife of Angels (La vie rêvée des anges) • France
• Best Non-Fiction Film:
  • Buena Vista Social Club
  • Runner-up: Mr. Death: The Rise and Fall of Fred A. Leuchter, Jr.
• Best Animation:
  • The Iron Giant
• The Douglas Edwards Experimental/Independent Film/Video Award:
  • Owen Land
• New Generation Award:
  • Alexander Payne and Jim Taylor – Citizen Ruth and Election
• Career Achievement Award:
  • Dede Allen
• Special Citation:
  • Rick Schmidlin, Roger Mayer, and Turner Classic Movies for their meticulous reconstruction and promotion of Erich von Stroheim's Greed