The 1999 Academy Awards were presented March 26, 2000 at the Los Angeles Shrine Auditorium.
Best Picture | American Beauty, Bruce Cohen and Dan Jinks, producers (DreamWorks SKG) |
| The Cider House Rules, Richard N. Gladstein, producer (Miramax) |
| The Green Mile, David Valdes and Frank Darabont, producers (Warner Bros.) |
| The Insider, Michael Mann and Pieter Jan Brugge, producers (Touchstone) |
| The Sixth Sense, Frank Marshall, Kathleen Kennedy, and Barry Mendel, producers (Hollywood) |
Actor in a Leading Role | Russell Crowe, The Insider |
| Richard Farnsworth, The Straight Story |
| Sean Penn, Sweet and Lowdown |
| Kevin Spacey, American Beauty |
| Denzel Washington, The Hurricane |
Actress in a Leading Role | Annette Bening, American Beauty |
| Janet McTeer, Tumbleweeds |
| Julianne Moore, The End of the Affair |
| Meryl Streep, Music of the Heart |
| Hilary Swank, Boys Don't Cry |
Actor in a Supporting Role | Michael Caine, The Cider House Rules |
| Tom Cruise, Magnolia |
| Michael Clarke Duncan, The Green Mile |
| Jude Law, The Talented Mr. Ripley |
| Haley Joel Osment, The Sixth Sense |
Actress in a Supporting Role | Toni Collette, The Sixth Sense |
| Angelina Jolie, Girl, Interrupted |
| Catherine Keener, Being John Malkovich |
| Samantha Morton, Sweet and Lowdown |
| Chloë Sevigny, Boys Don't Cry |
Directing | Sam Mendes, American Beauty |
| Spike Jonze, Being John Malkovich |
| Lasse Hallström, The Cider House Rules |
| Michael Mann, The Insider |
| M. Night Shyamalan, The Sixth Sense |
Writing | Screenplay Written Directly for the Screen | Alan Ball, American Beauty | | Charlie Kaufman, Being John Malkovich | | P. T. Anderson, Magnolia | | M. Night Shyamalan, The Sixth Sense | | Mike Leigh, Topsy-Turvy | Screenplay Based on Material Previously Produced or Published | John Irving, The Cider House Rules | | Alexander Payne and Jim Taylor, Election | | Frank Darabont, The Green Mile | | Eric Roth and Michael Mann, The Insider | | Anthony Minghella, The Talented Mr. Ripley |
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Cinematography | Conrad L. Hall, American Beauty |
| Roger Pratt, The End of the Affair |
| Dante Spinotti, The Insider |
| Emmanuel Lubezki, Sleepy Hollow |
| Robert Richardson, Snow Falling on Cedars |
Art Direction | Luciana Arrighi, Anna and the King |
| David Gropman, The Cider House Rules |
| Rick Heinrichs, Sleepy Hollow |
| Roy Walker, The Talented Mr. Ripley |
| Eve Stewart, Topsy-Tuvry |
Sound | Robert J. Litt, Elliot Tyson, Michael Herbick, and Willie D. Burton, The Green Mile |
| Andy Nelson, Doug Hemphill, and Lee Orloff, The Insider |
| John Reitz, Gregg Rudloff, David Campbell, and David Lee, The Matrix |
| Leslie Shatz, Chris Carpenter, Rick Kline, and Chris Munro, The Mummy |
| Gary Rydstrom, Tom Johnson, Shawn Murphy, and John Midgley, Star Wars: Episode I—The Phantom Menace |
Music | Song | “Blame Canada”, South Park: Bigger, Longer & Uncut, Trey Parker and Marc Shaiman | | “Music of My Heart,” Music of the Heart, Diane Warren | | “Save Me,” Magnolia, Aimee Mann | | “When She Loved Me,” Toy Story 2, Randy Newman | | “You'll Be in My Heart,” Tarzan, Phil Collins | Original Score | Thomas Newman, American Beauty | | John Williams, Angela's Ashes | | Rachel Portman, The Cider House Rules | | John Corigliano, The Red Violin | | Gabriel Yared, The Talented Mr. Ripley |
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Film Editing | Tariq Anwar, American Beauty |
| Lisa Zeno Churgin, The Cider House Rules |
| William Goldenberg, Paul Rubell, and David Rosenbloom, The Insider |
| Zach Staenberg, The Matrix |
| Andrew Mondshein, The Sixth Sense |
Costume Design | Jenny Beavan, Anna and the King |
| Colleen Atwood, Sleepy Hollow |
| Ann Roth and Gary Jones, The Talented Mr. Ripley |
| Milena Canonero, Titus |
| Lindy Hemming, Topsy-Turvy |
Makeup | Michèle Burke and Mike Smithson, Austin Powers: The Spy Who Shagged Me |
| Greg Cannom, Bicentennial Man |
| Rick Baker, Life |
| Christine Blundell and Trefor Proud, Topsy-Turvy |
Visual Effects | John Gaeta, Janek Sirrs, Steve Courtley, and Jon Thum, The Matrix |
| John Knoll, Dennis Muren, Scott Squires, and Rob Coleman, Star Wars: Episode I—The Phantom Menace |
| John Dykstra, Jerome Chen, Henry F. Anderson, III, and Eric Allard, Stuart Little |
Sound Effects Editing | Ren Klyce and Richard Hymns, Fight Club |
| Dane A. Davis, The Matrix |
| Ben Burtt and Tom Bellfort, Star Wars: Episode I—The Phantom Menace |
Short Films | Animation | Humdrum(Peter Peake ) | | My Grandmother Ironed the King's Shirts (Torill Kove) | | The Old Man and the Sea(Alexandre Petrov) | | 3 Misses (Paul Driessen) | | When the Day Breaks(Wendy Tilby and Amanda Forbis) | Live Action | Bror, Min Bro (Henrik Ruben Genz and Michael W. Horsten) | | Killing Joe (Mehdi Norowzian and Steve Wax ) | | Kleingeld (Small Change) (Marc-Andreas Bochert and Gabriele Lins ) | | Major and Minor Miracles (Marcus Olsson) | | My Mother Dreams the Satan's Disciples in New York (Barbara Schock and Tamara Tiehel) |
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Documentary | Short Subject | Eyewitness (Bert Van Bork) | | King Gimp (Susan Hannah Hadary and William A. Whiteford) | | The Wildest Show in the South: The Angola Prison Rodeo (Simeon Soffer and Jonathan Stack) | Feature | Buena Vista Social Club (Wim Wenders and Ulrich Felsberg) | | Genghis Blues (Roko Belic and Adrian Belic) | | On the Ropes (Nanette Burstein and Brett Morgen) | | One Day in September (Arthur Cohn) | | Speaking in Strings (Paola di Florio and Lilibet Foster) |
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Foreign Language Film | All About My Mother, Spain |
| Caravan, Nepal |
| East-West, France |
| Solomon and Gaenor, United Kingdom |
| Under the Sun, Sweden |
Irving G. Thalberg Award | Warren Beatty, producer, director, writer, actor |
Gordon E. Sawyer Award (Technological contribution) | Dr. Roderick T. Ryan |
Honorary Award | Andrzej Wajda, director |