My top films of 1999
by larsonlo | created - 03 Mar 2011 | updated - 21 Sep 2016 | PublicMy top films of 1999. Includes features, shorts, and docs. All films 7/10 or above. Note: I haven't seen all films released in 1999.
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1. American Beauty (1999)
R | 122 min | Drama
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: 1,211,549 | Gross: $130.10M
2. Fight Club (1999)
R | 139 min | Drama
An insomniac office worker and a devil-may-care soap maker form an underground fight club that evolves into much more.
Director: David Fincher | Stars: Brad Pitt, Edward Norton, Meat Loaf, Zach Grenier
Votes: 2,325,904 | Gross: $37.03M
3. 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.
Directors: John Lasseter, Ash Brannon, Lee Unkrich | Stars: Tom Hanks, Tim Allen, Joan Cusack, Kelsey Grammer
Votes: 620,083 | Gross: $245.85M
4. The Green Mile (1999)
R | 189 min | Crime, Drama, Fantasy
A tale set on death row, where gentle giant John Coffey possesses the mysterious power to heal people's ailments. When the lead guard, Paul Edgecombe, recognizes John's gift, he tries to help stave off the condemned man's execution.
Director: Frank Darabont | Stars: Tom Hanks, Michael Clarke Duncan, David Morse, Bonnie Hunt
Votes: 1,408,525 | Gross: $136.80M
5. 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.
Directors: Lana Wachowski, Lilly Wachowski | Stars: Keanu Reeves, Laurence Fishburne, Carrie-Anne Moss, Hugo Weaving
Votes: 2,054,819 | Gross: $171.48M
6. The Iron Giant (1999)
PG | 86 min | Animation, Action, Adventure
A young boy befriends a giant robot from outer space that a paranoid government agent wants to destroy.
Director: Brad Bird | Stars: Eli Marienthal, Harry Connick Jr., Jennifer Aniston, Vin Diesel
Votes: 227,678 | Gross: $23.16M
7. Office Space (1999)
R | 89 min | Comedy
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: 287,762 | Gross: $10.82M
8. 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.
Director: Joe Johnston | Stars: Jake Gyllenhaal, Chris Cooper, Laura Dern, Chris Owen
Votes: 98,097 | Gross: $32.48M
9. The Straight Story (1999)
G | 112 min | Biography, Drama
An old man makes a long journey by lawnmower to mend his relationship with an ill brother.
Director: David Lynch | Stars: Richard Farnsworth, Sissy Spacek, Jane Galloway Heitz, Joseph A. Carpenter
Votes: 97,539 | Gross: $6.20M
10. The Hurricane (1999)
R | 146 min | Biography, Drama, Sport
The story of Rubin 'Hurricane' Carter, a boxer wrongly imprisoned for murder, and the people who aided in his fight to prove his innocence.
Director: Norman Jewison | Stars: Denzel Washington, Vicellous Shannon, Deborah Kara Unger, Liev Schreiber
Votes: 102,520 | Gross: $50.67M
11. The Sixth Sense (1999)
PG-13 | 107 min | Drama, Mystery, Thriller
Malcolm Crowe, a child psychologist, starts treating a young boy, Cole, who encounters dead people and convinces him to help them. In turn, Cole helps Malcolm reconcile with his estranged wife.
Director: M. Night Shyamalan | Stars: Bruce Willis, Haley Joel Osment, Toni Collette, Olivia Williams
Votes: 1,051,987 | Gross: $293.51M
12. Bowfinger (1999)
PG-13 | 97 min | Comedy
When a desperate movie producer fails to get a major star for his bargain-basement film, he decides to shoot the film secretly around him.
Director: Frank Oz | Stars: Steve Martin, Eddie Murphy, Heather Graham, Christine Baranski
Votes: 73,983 | Gross: $66.38M
13. Butterfly (1999)
R | 96 min | Drama, War
Based in 1936 Spain, Moncho is an outcast at school but is able to form a strong bond with his outspoken teacher. When fascism arrives to Spain, his teacher is considered an enemy of the regime & arrested.
Director: José Luis Cuerda | Stars: Manuel Lozano, Fernando Fernán Gómez, Uxía Blanco, Gonzalo Uriarte
Votes: 9,758 | Gross: $2.09M
14. The Insider (1999)
R | 157 min | Biography, Drama, Thriller
A research chemist comes under personal and professional attack when he decides to appear in a 60 Minutes exposé on Big Tobacco.
Director: Michael Mann | Stars: Russell Crowe, Al Pacino, Christopher Plummer, Diane Venora
Votes: 180,312 | Gross: $28.97M
15. Man on the Moon (1999)
R | 118 min | Biography, Comedy, Drama
The life and career of legendary comedian Andy Kaufman.
Director: Milos Forman | Stars: Jim Carrey, Danny DeVito, Gerry Becker, Greyson Erik Pendry
Votes: 137,540 | Gross: $34.58M
16. The Cider House Rules (1999)
PG-13 | 126 min | Drama, Romance
A compassionate young man, raised in an orphanage and trained to be a doctor there, decides to leave to see the world.
Director: Lasse Hallström | Stars: Tobey Maguire, Charlize Theron, Michael Caine, Delroy Lindo
Votes: 104,852 | Gross: $57.55M
17. Spring Forward (1999)
R | 110 min | Drama
An ex convict befriends an elderly coworker as they both try to find meaning in life and forgiveness for their past.
Director: Tom Gilroy | Stars: Campbell Scott, Ned Beatty, Liev Schreiber, Ian Hart
Votes: 1,499 | Gross: $0.10M
18. Being John Malkovich (1999)
R | 113 min | Comedy, Drama, Fantasy
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: 353,480 | Gross: $22.86M
19. Magnolia (1999)
R | 188 min | Drama
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: 328,660 | Gross: $22.46M
20. Kikujiro (1999)
PG-13 | 122 min | Drama, Comedy
A young, naive boy sets out alone on the road to find his wayward mother. Soon he finds an unlikely protector in a crotchety man and the two have a series of unexpected adventures along the way.
Director: Takeshi Kitano | Stars: Takeshi Kitano, Yusuke Sekiguchi, Kayoko Kishimoto, The Great Gidayû
Votes: 22,182 | Gross: $0.20M
21. Big Daddy (1999)
PG-13 | 93 min | Comedy, Drama
A lazy law school graduate adopts a kid to impress his girlfriend, but everything doesn't go as planned.
Director: Dennis Dugan | Stars: Adam Sandler, Joey Lauren Adams, Jon Stewart, Cole Sprouse
Votes: 234,341 | Gross: $163.48M
22. Instinct (1999)
R | 126 min | Drama, Thriller
When noted anthropologist Dr. Ethan Powell, who left society to live in the jungle, is imprisoned for murder, it's up to young psychiatrist Theo Caulder to get through to him.
Director: Jon Turteltaub | Stars: Anthony Hopkins, Cuba Gooding Jr., Donald Sutherland, Maura Tierney
Votes: 34,297 | Gross: $34.10M
23. Boys Don't Cry (1999)
R | 118 min | Biography, Crime, Drama
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: 103,329 | Gross: $11.53M
24. 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".
Director: Jay Roach | Stars: Mike Myers, Heather Graham, Michael York, Robert Wagner
Votes: 248,957 | Gross: $206.04M
25. Eyes Wide Shut (1999)
R | 159 min | Drama, Mystery, Thriller
A Manhattan doctor embarks on a bizarre, night-long odyssey after his wife's admission of unfulfilled longing.
Director: Stanley Kubrick | Stars: Tom Cruise, Nicole Kidman, Todd Field, Sydney Pollack
Votes: 375,418 | Gross: $55.69M
26. Himalaya (1999)
108 min | Drama
An aging chief's last stand, lessons for the new, and the education of a young chief-to-be played against harsh Nature in Nepal's Dolpo. When his son dies returning from Tibet's salt lakes,... See full summary »
Directors: Eric Valli, Michel Debats | Stars: Thilen Lhondup, Gurgon Kyap, Lhakpa Tsamchoe, Karma Wangel
Votes: 5,693 | Gross: $2.48M
27. The Talented Mr. Ripley (1999)
R | 139 min | Crime, Drama, Thriller
In late 1950s New York, a young underachiever named Tom Ripley 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: 243,765 | Gross: $81.30M
28. Analyze This (1999)
R | 103 min | Comedy, Crime
A comedy about a psychiatrist whose number-one patient is an insecure mob boss.
Director: Harold Ramis | Stars: Robert De Niro, Billy Crystal, Lisa Kudrow, Chazz Palminteri
Votes: 161,743 | Gross: $106.89M
29. After the Rain (1999)
91 min | Drama
During a downpour, a generous ronin and his supporting wife are stranded at a country inn. The ronin comes to the attention of a lord who wants to hire him as an instructor for his men, who treat the ronin with disrespect.
Director: Takashi Koizumi | Stars: Akira Terao, Yoshiko Miyazaki, Shirô Mifune, Fumi Dan
Votes: 4,464
30. Mickey's Once Upon a Christmas (1999 Video)
Not Rated | 66 min | Animation, Comedy, Family
Three tales of Christmas past about Donald's nephews reliving the day on repeat, Max Goof's belief in Santa being challenged, and Mickey and Minnie making ends meet.
Directors: Jun Falkenstein, Alex Mann, Bradley Raymond, Toby Shelton, Bill Speers | Stars: Kelsey Grammer, Wayne Allwine, Russi Taylor, Tony Anselmo
Votes: 10,403
31. American Pie (1999)
R | 95 min | Comedy
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: 434,023 | Gross: $102.56M
32. Sleepy Hollow (1999)
R | 105 min | Fantasy, Horror, Mystery
Ichabod Crane is sent to Sleepy Hollow to investigate the decapitations of three people; the culprit is legendary apparition The Headless Horseman.
Director: Tim Burton | Stars: Johnny Depp, Christina Ricci, Miranda Richardson, Michael Gambon
Votes: 384,082 | Gross: $101.07M
33. Tuesdays with Morrie (1999 TV Movie)
TV-G | 89 min | Biography, Drama
A journalist finds himself questioning his own life when his best friend, a dying man, offers him some very powerful wisdom and advice for coping in relationships, careers and society.
Director: Mick Jackson | Stars: Jack Lemmon, Hank Azaria, Wendy Moniz, Caroline Aaron
Votes: 4,911
34. Jakob the Liar (1999)
PG-13 | 120 min | Drama, War
During World War II, an ordinary inhabitant of a ghetto fakes news about Allied offensives to inspire hope for other victims of the Nazi regime.
Director: Peter Kassovitz | Stars: Robin Williams, Hannah Taylor Gordon, Éva Igó, István Bálint
Votes: 18,004 | Gross: $4.96M
35. Life (I) (1999)
R | 108 min | Comedy, Crime, Drama
In 1932, two strangers are wrongfully convicted and develop a strong friendship in prison that lasts them through the 20th century.
Director: Ted Demme | Stars: Eddie Murphy, Martin Lawrence, Obba Babatundé, Nick Cassavetes
Votes: 54,812 | Gross: $63.84M
36. 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.
Director: Troy Duffy | Stars: Willem Dafoe, Sean Patrick Flanery, Norman Reedus, David Della Rocco
Votes: 250,781 | Gross: $0.03M
37. 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.
Director: George Lucas | Stars: Ewan McGregor, Liam Neeson, Natalie Portman, Jake Lloyd
Votes: 857,425 | Gross: $474.54M
38. The Ninth Gate (1999)
R | 133 min | Mystery, Thriller
A book broker discovers his latest find may summon Satan.
Director: Roman Polanski | Stars: Johnny Depp, Frank Langella, Lena Olin, Emmanuelle Seigner
Votes: 197,602 | Gross: $18.66M
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