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1999 12th Chicago Film Critics Awards
 Best Picture
 * American Beauty
 Being John Malkovich
 The Insider
 Magnolia
 The Straight Story
 
 Best Foreign Language Film
 * All About My Mother - Spain
 Afterlife - Japan
 Autumn Tale - France
 Lovers on the Bridge - France
 Run Lola Run - Germany
 
 Best Director
 * Sam Mendes - American Beauty
 Paul T. Anderson - Magnolia
 Spike Jonze - Being John Malkovich
 Stanley Kubrick - Eyes Wide Shut
 David Lynch - The Straight Story
 
 Best Actor
 * Kevin Spacey - American Beauty
 Jim Broadbent - Topsy-Turvy
 Russell Crowe - The Insider
 Richard Farnsworth - The Straight Story
 Denzel Washington - The Hurricane
 
 Best Actress
 * Hilary Swank - Boys Don't Cry
 Annette Bening - American Beauty
 Janet McTeer - Tumbleweeds
 Julianne Moore - The End of the Affair
 Reese Witherspoon - Election
 
 Best Supporting Actor
 * Tom Cruise - Magnolia
 Michael Clarke Duncan - The Green Mile
 John Malkovich - Being John Malkovich
 Haley Joel Osment - The Sixth Sense
 Christopher Plummer - The Insider
 
 Best Supporting Actress
 * Chloe Sevigny - Boys Don't Cry
 Angelina Jolie - Girl, Interrupted
 Catherine Keener - Being John Malkovich
 Julianne Moore - An Ideal Husband
 Samantha Morton - Sweet and Lowdown
 
 Most Promising Actor
 * Wes Bentley - American Beauty
 Michael Clarke Duncan - The Green Mile
 Terrence Howard - Best Laid Plans
 Chris Klein - Election / American Pie
 Haley Joel Osment - The Sixth Sense
 
 Most Promising Actress
 * Emilie Dequenne - Rosetta
 * Julia Stiles - 10 Things I Hate About You
 Lara Belmont - The War Zone
 Janet McTeer - Tumbleweeds
 Samantha Morton - Sweet and Lowdown
 
 Best Screenplay
 * Being John Malkovich - Charlie Kaufman
 American Beauty - Alan Ball
 Magnolia - Paul T. Anderson
 The Sixth Sense - M. Night Shyamalan
 Topsy-Turvy - Mike Leigh
 
 Best Cinematography
 * Snow Falling on Cedars - Robert Richardson
 American Beauty - Conrad Hall
 Eyes Wide Shut - Larry Smith, Stanley Kubrick
 Sleepy Hollow - Emmanuel Lubezski
 The Talented Mr. Ripley - John Seale
 
 Best Score
 * South Park: Bigger, Longer & Uncut - Trey Parker, Marc Shaiman
 The Cider House Rules - Rachel Portman
 Eyes Wide Shut - Jocelyn Pook
 The Red Violin - John Corigliano
 Run Lola Run - Tom Tykwer, Johnny Klimek, Rheinhold Heil
 
 
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