The 20th Boston Society of Film Critics Awards honored the best films of 1999. The awards were given on 12 December 1999.

• Best Film:
  • Three Kings
• Best Actor:
  • Jim Carrey – Man on the Moon
• Best Actress:
  • Hilary Swank – Boys Don't Cry
• Best Supporting Actor:
  • Christopher Plummer – The Insider
• Best Supporting Actress:
  • Chloë Sevigny – Boys Don't Cry
• Best Director:
  • David O. Russell – Three Kings
• Best Screenplay:
  • Charlie Kaufman – Being John Malkovich
• Best Cinematography:
  • Emmanuel Lubezki – Sleepy Hollow
• Best Documentary:
  • Hands on a Hard Body: The Documentary
• Best Foreign-Language Film:
  • All About My Mother (Todo sobre mi madre) • Spain/ France
• Best New Filmmaker:
  • Kimberly Peirce – Boys Don't Cry

• Past Winners

• ‘Kings’ takes gold Variety
• `KINGS,' SWANK TOP BOSTON CRITIC PICKS^{[ permanent dead link]} The Boston Globe
• Boston film critics crown 'Three Kings' best picture hollywood.com
• 1999 Boston Society of Film Critics Awards Internet Movie Database