- 1
Chill Factor/In Too Deep/Dudley Do-Right/The Astronaut's Wife/All the Little Animals
- 2
Stir of Echoes/The Minus Man/Sugar Town/Best Laid Plans/On the Ropes
- 3
American Beauty/Blue Streak/For Love of the Game
- 4
Double Jeopardy/Jakob the Liar/Mumford
- 5
Three Kings/Happy, Texas/Guinevere/Mystery, Alaska/Drive Me Crazy
- 6
Superstar/Random Hearts/Boys Don't Cry/The Limey/Romance
- 7
Fight Club/The Straight Story/Julien Donkey-Boy/The Story of Us
- 8
Bringing Out the Dead/Body Shots/Crazy in Alabama/Three to Tango/The City
- 9
The Insider/Music of the Heart/Being John Malkovich/Princess Mononoke/Man of the Century
- 10
The Bone Collector/Last Night/Liberty Heights/The Bachelor/American Movie/The Legend of 1900
- 11
Anywhere But Here/Pokémon: The First Movie/Dogma/The Messenger/Felicia's Journey
- 12
Sleepy Hollow/42 Up/The World Is Not Enough/Mansfield Park/Rosetta
- 13
End of Days/Tumbleweeds/Flawless/Toy Story 2/All About My Mother
- 14
The Green Mile/The End of the Affair/A Map of the World/Sweet and Lowdown/Mr. Death
- 15
Man on the Moon/Deuce Bigalow: Male Gigolo/Cradle Will Rock/The Cider House Rules/The War Zone
- 16
Magnolia/Stuart Little/Anna and the King/Bicentennial Man/Topsy-Turvy
- 17
Any Given Sunday/Fantasia 2000/Galaxy Quest/The Talented Mr. Ripley/The Hurricane
- 18
The Best Films of 1999
- 19
The Worst Films of 1999
- 20
Play It to the Bone/Girl, Interrupted/Angela's Ashes/Snow Falling on Cedars/The Terrorist
- 21
Simpatico/The Third Miracle/Titus...Memo to the Academy
- 22
'Cult' Movies
- 23
The Bill Clinton Interview
- 24
The Beach/Snow Day/Holy Smoke
- 25
Wonder Boys/Boiler Room/The Whole Nine Yards/Hanging Up/Pitch Black
- 26
Best of the '90s
- 27
Drowning Mona/My Dog Skip/What Planet Are You From?/The Next Best Thing/Miss Julie
- 28
Mission to Mars/Ghost Dog/Agnes Browne/Deterrence
- 29
Erin Brockovich/Final Destination/The Ninth Gate/Onegin/Paradise Lost 2: Revelations
- 30
Waking the Dead/Here on Earth/Romeo Must Die
- 31
High Fidelity/The Road to El Dorado/Price of Glory
- 32
Return to Me/Black and White/Ready to Rumble/Rules of Engagement/Me Myself I
- 33
28 Days/Keeping the Faith/Where the Money Is/American Psycho/East is East
- 34
U-571/Love & Basketball/Joe Gould's Secret/Gossip/Pups
- 35
Where the Heart Is/The Last September/The Flintstones in Viva Rock Vegas/Frequency/Time Code
- 36
Gladiator/Up at the Villa/Committed/I Dreamed of Africa/The Virgin Suicides
- 37
Battlefield Earth/The Big Kahuna/Hamlet/Michael Jordan to the Max/Center Stage
- 38
Dinosaur/Road Trip/Small Time Crooks/Shanghai Noon