Oscar Nominations and Winners (1999)
Best Picture
- American Beauty
- The Cider House Rules
- The Green Mile
- The Insider
- The Sixth Sense
Best Director
- Lasse Hallstrom (The Cider House Rules)
- Spike Jonze (Being John Malkovich)
- Michael Mann (The Insider)
- Sam Mendes (American Beauty)
- M. Night Shyamalan (The Sixth Sense)
Best Actor in a Leading Role
- Russell Crowe (The Insider)
- Richard Farnsworth (The Straight Story)
- Sean Penn (Sweet and Lowdown)
- Kevin Spacy (American Beauty)
- Denzel Washington (The Hurricane)
Best 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)
Best 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)
Best Actress in a Supporting Role
- Toni Collette (The Sixth Sense)
- Angelina Jolie (Girl, Interrupted)
- Catherine Keener (Being John Malkovich)
- Samantha Morton (Sweet and Lowdown)
- Chloe Sevigny (Boys Don't Cry)
Best Adapted Screenplay
- The Cider House Rules (John Irving)
- Election (Alexander Payne and Jim Taylor)
- The Green Mile (Frank Darabont)
- The Insider (Eric Roth and Michael Mann)
- The Talented Mr. Ripley (Anthony Minghella)
Best Original Screenplay
- American Beauty (Alan Ball)
- Being John Malkovich (Charlie Kaufman)
- Magnolia (Paul Thomas Anderson)
- The Sixth Sense (M. Night Shyamalan)
- Topsy-Turvy (Mike Leigh)
Best Foreign Language Film
- All About My Mother (Spain)
- Caravan
- East-West
- Solomon and Gaenor
- Under the Sun
Art Direction
- Anna and the King
- The Cider House Rules
- Sleepy Hollow
- The Talented Mr. Ripley
- Topsy-Turvy
Cinematography
- American Beauty
- The End of the Affair
- The Insider
- Sleepy Hollow
- Snow Falling on Cedars
Costume Design
- Anna and the King
- Sleepy Hollow
- The Talented Mr. Ripley
- Titus
- Topsy-Turvy
Documentary Feature
- Buena Vista Social Club
- Genghis Rules
- On the Ropes
- One Day in September
- Speaking in Strings
Documentary Short Subject
- Eyewitness
- King Gimp
- Wildest Show in the South: The Angola
Film Editing
- American Beauty
- The Cider House Rules
- The Insider
- The Matrix
- The Sixth Sense
Makeup
- Austin Powers: The Spy Who Shagged Me
- Bicentennial Man
- Life
- Topsy-Turvy
Original Score
- American Beauty (Thomas Newman)
- Angela's Ashes (John Williams)
- The Cider House Rules (Rachel Portman)
- The Red Violin (John Corigliano)
- The Talented Mr. Ripley (Gabriel Yared)
Original Song
- "Blame Canada" (South Park: Bigger, Longer & Uncut) by Trey Parker and Matt Stone
- "Music of the Heart" (Music of the Heart) by NSync and Gloria Estefan
- "Save Me" (Magnolia) by Aimee Mann
- "When She Loved Me" (Toy Story 2) by Sarah McLachlan
- "You'll Be in My Heart" (Tarzan) by Phil Collins
Animated Short Film
- Humdrum
- My Grandmother Ironed the King's Shirts
- The Old Man and the Sea
- 3 Misses
- When The Day Breaks
Live Action Short Film
- Bror, Min Bror
- Killing Joe
- Kleingeld
- Major And Minor Miracles
- My Mother Dreams The Satan's Disciples In New York
Sound
- The Green Mile
- The Insider
- The Matrix
- The Mummy
- Star Wars, Episode 1: The Phantom Menace
Sound Editing
- Fight Club
- The Matrix
- Star Wars, Episode 1: The Phantom Menace
Visual Effects
- The Matrix
- Star Wars, Episode 1: The Phantom Menace
- Stuart Little