Feature Film, Released between 1999-01-01 and 1999-12-31 (Sorted by Popularity Ascending)
1. Sleepy Hollow (1999)
R | 105 min | Fantasy, Horror, Mystery
Ichabod Crane is sent to Sleepy Hollow to investigate the decapitations of three people, with the culprit being the legendary apparition, The Headless Horseman.
Votes: 326,854 | Gross: $101.07M
2. The Matrix (1999)
R | 136 min | Action, Sci-Fi
When a beautiful stranger leads computer hacker Neo to a forbidding underworld, he discovers the shocking truth--the life he knows is the elaborate deception of an evil cyber-intelligence.
Votes: 1,645,621 | Gross: $171.48M
5. The Green Mile (1999)
R | 189 min | Crime, Drama, Fantasy
The lives of guards on Death Row are affected by one of their charges: a black man accused of child murder and rape, yet who has a mysterious gift.
Votes: 1,123,737 | Gross: $136.80M
7. Big Daddy (1999)
PG-13 | 93 min | Comedy, Drama
A lazy law school grad adopts a kid to impress his girlfriend, but everything doesn't go as planned and he becomes the unlikely foster father.
Votes: 197,204 | Gross: $163.48M
8. Eyes Wide Shut (1999)
R | 159 min | Drama, Mystery, Thriller
A New York City doctor embarks on a harrowing, night-long odyssey of sexual and moral discovery after his wife reveals a painful secret to him.
Votes: 297,446 | Gross: $55.69M
10. The Haunting (1999)
PG-13 | 113 min | Fantasy, Horror, Mystery
A study in fear escalates into a heart-stopping nightmare for a professor and three subjects trapped in a mysterious mansion.
Votes: 70,825 | Gross: $91.41M
11. The Mummy (1999)
PG-13 | 124 min | Action, Adventure, Fantasy
At an archaeological dig in the ancient city of Hamunaptra, an American serving in the French Foreign Legion accidentally awakens a mummy who begins to wreck havoc as he searches for the reincarnation of his long-lost love.
Votes: 386,217 | Gross: $155.25M
12. Star Wars: Episode I - The Phantom Menace (1999)
PG | 136 min | Action, Adventure, Fantasy
Two Jedi escape a hostile blockade to find allies and come across a young boy who may bring balance to the Force, but the long dormant Sith resurface to claim their original glory.
Votes: 717,806 | Gross: $474.54M
13. The Virgin Suicides (1999)
R | 97 min | Drama, Romance
A group of male friends become obsessed with five mysterious sisters who are sheltered by their strict, religious parents in suburban Detroit in the mid 1970s.
Votes: 142,498 | Gross: $4.86M
15. The Blair Witch Project (1999)
R | 81 min | Horror, Mystery
Three film students vanish after traveling into a Maryland forest to film a documentary on the local Blair Witch legend, leaving only their footage behind.
Votes: 229,396 | Gross: $140.54M
16. Cruel Intentions (1999)
R | 97 min | Drama, Romance
Two vicious step-siblings of an elite Manhattan prep school make a wager: to deflower the new headmaster's daughter before the start of term.
Votes: 177,269 | Gross: $38.33M
23. House on Haunted Hill (1999)
R | 93 min | Crime, Fantasy, Horror
An amusement park mogul offers a group of diverse people $1,000,000 to spend the night in a haunted house with a horrifying past.
Votes: 52,902 | Gross: $40.85M
24. Deep Blue Sea (1999)
R | 105 min | Action, Adventure, Sci-Fi
Searching for a cure to Alzheimer's disease, a group of scientists on an isolated research facility become the prey, as a trio of intelligent sharks fight back.
Votes: 123,696 | Gross: $73.65M
25. Galaxy Quest (1999)
PG | 102 min | Adventure, Comedy, Sci-Fi
The alumni cast of a space opera television series have to play their roles as the real thing when an alien race needs their help. However, they also have to defend both Earth and the alien race from a reptilian warlord.
Votes: 146,980 | Gross: $71.58M
26. Audition (1999)
R | 115 min | Drama, Horror, Mystery
A widower takes an offer to screen girls at a special audition, arranged for him by a friend to find him a new wife. The one he fancies is not who she appears to be after all.
28. The World Is Not Enough (1999)
PG-13 | 128 min | Action, Adventure, Thriller
James Bond uncovers a nuclear plot while protecting an oil heiress from her former kidnapper, an international terrorist who can't feel pain.
Votes: 186,089 | Gross: $126.94M
30. The Talented Mr. Ripley (1999)
R | 139 min | Crime, Drama, Thriller
In late 1950s New York, Tom Ripley, a young underachiever, is sent to Italy to retrieve Dickie Greenleaf, a rich and spoiled millionaire playboy. But when the errand fails, Ripley takes extreme measures.
Votes: 179,357 | Gross: $81.30M
31. Stir of Echoes (1999)
R | 99 min | Horror, Mystery, Thriller
After being hypnotized by his sister-in-law, a man begins seeing haunting visions of a girl's ghost and a mystery begins to unfold around him.
Votes: 74,328 | Gross: $21.13M
32. The Ninth Gate (1999)
R | 133 min | Mystery, Thriller
A rare book dealer, while seeking out the last two copies of a demon text, gets drawn into a conspiracy with supernatural overtones.
Votes: 165,208 | Gross: $18.66M
33. Wild Wild West (1999)
PG-13 | 106 min | Action, Comedy, Sci-Fi
The two best special agents in the Wild West must save President Grant from the clutches of a diabolical, wheelchair-bound, steampunk-savvy, Confederate scientist bent on revenge for losing the Civil War.
Votes: 151,722 | Gross: $113.81M
34. Toy Story 2 (1999)
G | 92 min | Animation, Adventure, Comedy
When Woody is stolen by a toy collector, Buzz and his friends set out on a rescue mission to save Woody before he becomes a museum toy property with his roundup gang Jessie, Prospector, and Bullseye.
Votes: 518,616 | Gross: $245.85M
35. Double Jeopardy (1999)
R | 105 min | Crime, Drama, Mystery
A woman framed for her husband's murder suspects he is still alive; as she has already been tried for the crime, she can't be re-prosecuted if she finds and kills him.
Votes: 73,287 | Gross: $116.74M
39. Dogma (1999)
R | 130 min | Adventure, Comedy, Drama
An abortion clinic worker with a special heritage is called upon to save the existence of humanity from being negated by two renegade angels trying to exploit a loop-hole and reenter Heaven.
Votes: 206,323 | Gross: $30.65M
40. Austin Powers: The Spy Who Shagged Me (1999)
PG-13 | 95 min | Action, Adventure, Comedy
Dr. Evil is back and has invented a new time machine that allows him to go back to the 1960s and steal Austin Powers' mojo, inadvertently leaving him "shagless".
Votes: 214,509 | Gross: $206.04M
41. The Boondock Saints (1999)
R | 108 min | Action, Crime, Thriller
Two Irish Catholic brothers become vigilantes and wipe out Boston's criminal underworld in the name of God.
Votes: 225,483 | Gross: $0.03M
44. The Thomas Crown Affair (1999)
R | 113 min | Crime, Romance, Thriller
A very rich and successful playboy amuses himself by stealing artwork, but may have met his match in a seductive detective.
Votes: 85,883 | Gross: $69.30M
45. October Sky (1999)
PG | 108 min | Biography, Drama, Family
The true story of Homer Hickam, a coal miner's son who was inspired by the first Sputnik launch to take up rocketry against his father's wishes.
Votes: 81,379 | Gross: $32.48M
46. Drop Dead Gorgeous (1999)
PG-13 | 97 min | Comedy, Romance, Thriller
A small-town beauty pageant turns deadly as it becomes clear that someone will go to any lengths to win.
Votes: 32,189 | Gross: $10.56M
47. Romance (1999)
R | 84 min | Drama, Romance
Frustrated by the lack of intimacy in her relationship, a young schoolteacher goes through a series of intimidating and often violent sexual partners.
Votes: 9,792 | Gross: $1.28M
49. For Love of the Game (1999)
PG-13 | 137 min | Drama, Romance, Sport
After 19 years of playing the game he's loved his whole life, Detroit Tigers pitcher Billy Chapel has to decide if he's going to risk everything and put everything out there.
Votes: 31,477 | Gross: $35.17M
50. Jawbreaker (1999)
R | 87 min | Comedy, Crime, Thriller
Three of the most popular girls at Reagan High accidentally kill the prom queen with a jawbreaker when a kidnapping goes horribly wrong.
Votes: 23,998 | Gross: $3.07M