1990s

by jeremygilbert-81746 | created - 1 month ago | updated - 1 month ago | Public
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1. The Matrix (1999)

R | 136 min | Action, Sci-Fi

73 Metascore

A computer hacker learns from mysterious rebels about the true nature of his reality and his role in the war against its controllers.

Directors: Lana Wachowski, Lilly Wachowski | Stars: Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss, Hugo Weaving

Votes: 1,579,519 | Gross: $171.48M

2. The Green Mile (1999)

R | 189 min | Crime, Drama, Fantasy

61 Metascore

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.

Director: Frank Darabont | Stars: Tom Hanks, Michael Clarke Duncan, David Morse, Bonnie Hunt

Votes: 1,070,238 | Gross: $136.80M

3. Fight Club (1999)

R | 139 min | Drama

66 Metascore

An insomniac office worker and a devil-may-care soapmaker form an underground fight club that evolves into something much, much more.

Director: David Fincher | Stars: Brad Pitt, Edward Norton, Meat Loaf, Zach Grenier

Votes: 1,752,065 | Gross: $37.03M

4. American Beauty (1999)

R | 122 min | Drama

84 Metascore

A sexually frustrated suburban father has a mid-life crisis after becoming infatuated with his daughter's best friend.

Director: Sam Mendes | Stars: Kevin Spacey, Annette Bening, Thora Birch, Wes Bentley

Votes: 1,022,613 | Gross: $130.10M

5. Eyes Wide Shut (1999)

R | 159 min | Drama, Mystery, Thriller

68 Metascore

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.

Director: Stanley Kubrick | Stars: Tom Cruise, Nicole Kidman, Todd Field, Sydney Pollack

Votes: 283,735 | Gross: $55.69M

6. Galaxy Quest (1999)

PG | 102 min | Adventure, Comedy, Sci-Fi

70 Metascore

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.

Director: Dean Parisot | Stars: Tim Allen, Sigourney Weaver, Alan Rickman, Tony Shalhoub

Votes: 141,921 | Gross: $71.58M

7. The Talented Mr. Ripley (1999)

R | 139 min | Crime, Drama, Thriller

76 Metascore

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.

Director: Anthony Minghella | Stars: Matt Damon, Gwyneth Paltrow, Jude Law, Cate Blanchett

Votes: 169,792 | Gross: $81.30M

8. American Pie (1999)

R | 95 min | Comedy

58 Metascore

Four teenage boys enter a pact to lose their virginity by prom night.

Directors: Paul Weitz, Chris Weitz | Stars: Jason Biggs, Chris Klein, Thomas Ian Nicholas, Jennifer Coolidge

Votes: 361,374 | Gross: $102.56M

9. The Mummy (1999)

PG-13 | 124 min | Action, Adventure, Fantasy

48 Metascore

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.

Director: Stephen Sommers | Stars: Brendan Fraser, Rachel Weisz, John Hannah, Arnold Vosloo

Votes: 375,981 | Gross: $155.25M

10. 10 Things I Hate About You (1999)

PG-13 | 97 min | Comedy, Drama, Romance

70 Metascore

A pretty, popular teenager can't go out on a date until her ill-tempered older sister does.

Director: Gil Junger | Stars: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larisa Oleynik

Votes: 280,073 | Gross: $38.18M

11. Magnolia (1999)

R | 188 min | Drama

77 Metascore

An epic mosaic of interrelated characters in search of love, forgiveness, and meaning in the San Fernando Valley.

Director: Paul Thomas Anderson | Stars: Tom Cruise, Jason Robards, Julianne Moore, Philip Seymour Hoffman

Votes: 277,699 | Gross: $22.46M

12. The Sixth Sense (1999)

PG-13 | 107 min | Drama, Mystery, Thriller

64 Metascore

A boy who communicates with spirits seeks the help of a disheartened child psychologist.

Director: M. Night Shyamalan | Stars: Bruce Willis, Haley Joel Osment, Toni Collette, Olivia Williams

Votes: 871,921 | Gross: $293.51M

13. Notting Hill (1999)

PG-13 | 124 min | Comedy, Drama, Romance

68 Metascore

The life of a simple bookshop owner changes when he meets the most famous film star in the world.

Director: Roger Michell | Stars: Hugh Grant, Julia Roberts, Richard McCabe, Rhys Ifans

Votes: 256,356 | Gross: $116.09M

14. Girl, Interrupted (1999)

R | 127 min | Biography, Drama

51 Metascore

Based on writer Susanna Kaysen's account of her 18-month stay at a mental hospital in the late 1960s.

Director: James Mangold | Stars: Winona Ryder, Angelina Jolie, Clea DuVall, Brittany Murphy

Votes: 154,197 | Gross: $28.87M

15. Office Space (1999)

R | 89 min | Comedy

68 Metascore

Three company workers who hate their jobs decide to rebel against their greedy boss.

Director: Mike Judge | Stars: Ron Livingston, Jennifer Aniston, David Herman, Ajay Naidu

Votes: 232,921 | Gross: $10.82M

16. Austin Powers: The Spy Who Shagged Me (1999)

PG-13 | 95 min | Action, Adventure, Comedy

59 Metascore

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".

Director: Jay Roach | Stars: Mike Myers, Heather Graham, Michael York, Robert Wagner

Votes: 209,416 | Gross: $206.04M

17. The World Is Not Enough (1999)

PG-13 | 128 min | Action, Adventure, Thriller

57 Metascore

James Bond uncovers a nuclear plot while protecting an oil heiress from her former kidnapper, an international terrorist who can't feel pain.

Director: Michael Apted | Stars: Pierce Brosnan, Sophie Marceau, Robert Carlyle, Denise Richards

Votes: 180,808 | Gross: $126.94M

18. The Bone Collector (1999)

R | 118 min | Crime, Drama, Mystery

45 Metascore

A quadriplegic ex-homicide detective and his partner try to track down a serial killer who is terrorizing New York City.

Director: Phillip Noyce | Stars: Denzel Washington, Angelina Jolie, Queen Latifah, Michael Rooker

Votes: 147,062 | Gross: $66.52M

19. She's All That (1999)

PG-13 | 95 min | Comedy, Romance

51 Metascore

A high school jock makes a bet that he can turn an unattractive girl into the school's prom queen.

Director: Robert Iscove | Stars: Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard, Paul Walker

Votes: 80,648 | Gross: $63.37M

20. Deep Blue Sea (1999)

R | 105 min | Action, Adventure, Sci-Fi

54 Metascore

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.

Director: Renny Harlin | Stars: Thomas Jane, Saffron Burrows, Samuel L. Jackson, Jacqueline McKenzie

Votes: 118,955 | Gross: $73.65M

21. Sleepy Hollow (1999)

R | 105 min | Fantasy, Horror, Mystery

65 Metascore

Ichabod Crane is sent to Sleepy Hollow to investigate the decapitations of three people, with the culprit being the legendary apparition, The Headless Horseman.

Director: Tim Burton | Stars: Johnny Depp, Christina Ricci, Miranda Richardson, Michael Gambon

Votes: 315,421 | Gross: $101.07M

22. Big Daddy (1999)

PG-13 | 93 min | Comedy, Drama

41 Metascore

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.

Director: Dennis Dugan | Stars: Adam Sandler, Joey Lauren Adams, Jon Stewart, Cole Sprouse

Votes: 190,944 | Gross: $163.48M

23. East Is East (1999)

R | 96 min | Comedy, Drama

74 Metascore

In early 1970s England, a Pakistani father finds the authority he has previously maintained challenged by his increasingly Anglicized children.

Director: Damien O'Donnell | Stars: Om Puri, Linda Bassett, Jordan Routledge, Archie Panjabi

Votes: 16,529 | Gross: $4.17M

24. Cruel Intentions (1999)

R | 97 min | Drama, Romance

56 Metascore

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.

Director: Roger Kumble | Stars: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair

Votes: 172,983 | Gross: $38.33M

25. The Virgin Suicides (1999)

R | 97 min | Drama, Romance

76 Metascore

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.

Director: Sofia Coppola | Stars: Kirsten Dunst, Josh Hartnett, James Woods, Kathleen Turner

Votes: 137,979 | Gross: $4.86M

26. Wild Wild West (1999)

PG-13 | 106 min | Action, Comedy, Sci-Fi

38 Metascore

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.

Director: Barry Sonnenfeld | Stars: Will Smith, Kevin Kline, Kenneth Branagh, Salma Hayek

Votes: 148,137 | Gross: $113.81M

27. The Ninth Gate (1999)

R | 133 min | Mystery, Thriller

44 Metascore

A rare book dealer, while seeking out the last two copies of a demon text, gets drawn into a conspiracy with supernatural overtones.

Director: Roman Polanski | Stars: Johnny Depp, Frank Langella, Lena Olin, Emmanuelle Seigner

Votes: 157,582 | Gross: $18.66M

28. The Boondock Saints (1999)

R | 108 min | Action, Crime, Thriller

44 Metascore

Two Irish Catholic brothers become vigilantes and wipe out Boston's criminal underworld in the name of God.

Director: Troy Duffy | Stars: Willem Dafoe, Sean Patrick Flanery, Norman Reedus, David Della Rocco

Votes: 221,194 | Gross: $0.03M

29. Being John Malkovich (1999)

R | 113 min | Comedy, Drama, Fantasy

90 Metascore

A puppeteer discovers a portal that leads literally into the head of movie star John Malkovich.

Director: Spike Jonze | Stars: John Cusack, Cameron Diaz, Catherine Keener, John Malkovich

Votes: 296,094 | Gross: $22.86M

30. End of Days (1999)

R | 122 min | Action, Fantasy, Horror

33 Metascore

At the end of the century, Satan visits New York in search of a bride. It's up to an ex-cop who now runs an elite security outfit to stop him.

Director: Peter Hyams | Stars: Arnold Schwarzenegger, Gabriel Byrne, Robin Tunney, Kevin Pollak

Votes: 102,612 | Gross: $66.89M

31. 200 Cigarettes (1999)

R | 101 min | Comedy, Drama, Romance

33 Metascore

A collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses.

Director: Risa Bramon Garcia | Stars: Ben Affleck, Casey Affleck, Dave Chappelle, Guillermo Díaz

Votes: 14,318 | Gross: $6.85M

32. The Blair Witch Project (1999)

R | 81 min | Horror, Mystery

81 Metascore

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.

Directors: Daniel Myrick, Eduardo Sánchez | Stars: Heather Donahue, Michael C. Williams, Joshua Leonard, Bob Griffin

Votes: 222,743 | Gross: $140.54M

33. Never Been Kissed (1999)

PG-13 | 107 min | Comedy, Drama, Romance

60 Metascore

A newspaper reporter enrolls in high school as part of research for a story.

Director: Raja Gosnell | Stars: Drew Barrymore, David Arquette, Michael Vartan, Molly Shannon

Votes: 79,749 | Gross: $55.47M

34. Double Jeopardy (1999)

R | 105 min | Crime, Drama, Mystery

40 Metascore

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.

Director: Bruce Beresford | Stars: Ashley Judd, Tommy Lee Jones, Bruce Greenwood, Benjamin Weir

Votes: 68,590 | Gross: $116.74M

35. Bicentennial Man (1999)

PG | 132 min | Comedy, Drama, Sci-Fi

42 Metascore

An android endeavors to become human as he gradually acquires emotions.

Director: Chris Columbus | Stars: Robin Williams, Embeth Davidtz, Sam Neill, Oliver Platt

Votes: 105,582 | Gross: $58.22M

36. Dogma (1999)

R | 130 min | Adventure, Comedy, Drama

62 Metascore

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.

Director: Kevin Smith | Stars: Ben Affleck, Matt Damon, Linda Fiorentino, Bud Cort

Votes: 202,667 | Gross: $30.65M

37. Boys Don't Cry (1999)

R | 118 min | Biography, Crime, Drama

86 Metascore

A young man named Brandon Teena navigates love, life, and being transgender in rural Nebraska.

Director: Kimberly Peirce | Stars: Hilary Swank, Chloë Sevigny, Peter Sarsgaard, Brendan Sexton III

Votes: 89,203 | Gross: $11.53M

38. The Thomas Crown Affair (1999)

R | 113 min | Crime, Romance, Thriller

72 Metascore

A very rich and successful playboy amuses himself by stealing artwork, but may have met his match in a seductive detective.

Director: John McTiernan | Stars: Pierce Brosnan, Rene Russo, Denis Leary, Ben Gazzara

Votes: 83,553 | Gross: $69.30M

39. The Insider (1999)

R | 157 min | Biography, Drama, Thriller

84 Metascore

A research chemist comes under personal and professional attack when he decides to appear in a 60 Minutes (1968) exposé on Big Tobacco.

Director: Michael Mann | Stars: Russell Crowe, Al Pacino, Christopher Plummer, Diane Venora

Votes: 153,584 | Gross: $28.97M

40. Varsity Blues (1999)

R | 106 min | Comedy, Drama, Romance

50 Metascore

A back-up quarterback is chosen to lead a Texas football team to victory after the star quarterback is injured.

Director: Brian Robbins | Stars: James Van Der Beek, Jon Voight, Paul Walker, Ron Lester

Votes: 40,313 | Gross: $52.89M

41. Three Kings (1999)

R | 114 min | Action, Adventure, Comedy

82 Metascore

In the aftermath of the Persian Gulf War, four soldiers set out to steal gold that was stolen from Kuwait, but they discover people who desperately need their help.

Director: David O. Russell | Stars: George Clooney, Mark Wahlberg, Ice Cube, Spike Jonze

Votes: 155,712 | Gross: $60.65M

42. Runaway Bride (1999)

PG | 116 min | Comedy, Romance

39 Metascore

A reporter is assigned to write a story about a woman who has left a string of fiancés at the altar.

Director: Garry Marshall | Stars: Julia Roberts, Richard Gere, Joan Cusack, Hector Elizondo

Votes: 89,463 | Gross: $152.26M

43. Entrapment (1999)

PG-13 | 113 min | Action, Crime, Romance

54 Metascore

An insurance agent is sent by her employer to track down and help capture an art thief.

Director: Jon Amiel | Stars: Sean Connery, Catherine Zeta-Jones, Ving Rhames, Will Patton

Votes: 103,046 | Gross: $87.70M

44. Anna and the King (1999)

PG-13 | 148 min | Drama, History, Romance