12th Chicago Film Critics Association Awards (1999)

Best Picture

	American Beauty
	Being John Malkovich
	The Insider
	Magnolia
	The Straight Story

Best Director

	Sam Mendes - American Beauty
	Paul Thomas 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

	Chloë Sevigny - Boys Don't Cry
	Angelina Jolie - Girl, Interrupted
	Catherine Keener - Being John Malkovich
	Julianne Moore - An Ideal Husband
	Samantha Morton - Sweet and Lowdown

Best Screenplay

	Being John Malkovich - Charlie Kaufman
	Magnolia - Paul Thomas Anderson
	American Beauty - Alan Ball
	The Sixth Sense - M. Night Shyamalan
	Topsy-Turvy - Mike Leigh

Best Cinematography

	Snow Falling on Cedars - Robert Richardson
	American Beauty - Conrad L. Hall
	Eyes Wide Shut - Larry Smith, Stanley Kubrick
	Sleepy Hollow - Emmanuel Lubezki
	The Talented Mr. Ripley - John Seale

Best Original Score

	South Park: Bigger, Longer & Uncut - Trey Parker, Marc Shaiman
	The Red Violin - John Corigliano
	Eyes Wide Shut - Jocelyn Pook
	The Cider House Rules - Rachel Portman
	Run Lola Run - Tom Tykwer, Johnny Klimek, Reinhold Heil

Best Foreign Language Film

	All About My Mother - Pedro Almodóvar
	Run Lola Run - Tom Tykwer
	After Life - Hirokazu Koreeda
	Autumn Tale - Éric Rohmer
	The Lovers on the Bridge - Leos Carax

Most Promising Actor

	Wes Bentley - American Beauty
	Michael Clarke Duncan - The Green Mile
	Terrence Howard - The Best Man
	Chris Klein - American Pie
	Haley Joel Osment - The Sixth Sense

Most Promising Actress

	Émilie Dequenne - Rosetta
	Julia Stiles - 10 Things I Hate About You
	The War Zone - Lara Belmont
	Janet McTeer - Tumbleweeds
	Samantha Morton - Sweet and Lowdown