Best Films Of 1999
by TheAnimalMother | created - 01 Oct 2013 | updated - 02 Nov 2022 | PublicEvery list of this nature is obviously a continuous work in progress.
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1. 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: 374,637 | Gross: $55.69M
2. 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: 197,301 | Gross: $18.66M
Perhaps no one loves this film as much as I do. I think you either get it or you don't with this one, the vibe of the film that is. And even more so the real spiritual aspect that the film has. Few even see it of course. Mostly the film is sort of aloof on purpose. Sort of like in Polanski's The Fearless Vampire Killers. Though of course that film is much more of an obvious comedy than The Ninth Gate is. Yet this also is definitely a comedy in its own right. I'd say that it really should be classified as a partial comedy. The film is also almost told in a fairytale type of way. The main character is only interested in these books. He doesn't really even seem to care or wonder if their is any reality to God and the devil at all. It has no importance to him, and his view on it is the general outside view, it's all a sham. He shrugs it off as nonsense. To me, the way this film plays with its subject matter is actually exceptional. Few films can even compare to it in this sense. Polanski as a filmmaker, despite what anyone wants to say or think truly is among the greatest of all time. This one was considered to be one of his rare misses by most critics. I think however for those that truly do get the vibe, and the depths of this film, it doesn't matter at all. Not nearly everyone is going to understand the deeper aspects and the playfulness of this film. Simply put, not everyone is going to see the brilliance buried in this beauty. I don't think you have to get the real spiritual aspect in the film to get the vibe either. The real spiritual aspect is definitely here, though it is not overly elaborate or anything. It's only a small aspect, but it is yet another interesting layer that adds even more to the story in my view. 9.5/10
3. 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: 2,050,193 | Gross: $171.48M
"Your mind makes it real" - Morpheus
9.5/10
4. 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: 1,209,814 | Gross: $130.10M
8.5/10
5. 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: 137,387 | Gross: $34.58M
6. Bringing Out the Dead (1999)
R | 121 min | Drama, Thriller
Haunted by the patients he failed to save, a monumentally burned-out Manhattan ambulance paramedic fights to maintain his sanity over three increasingly turbulent nights.
Director: Martin Scorsese | Stars: Nicolas Cage, Patricia Arquette, John Goodman, Ving Rhames
Votes: 76,001 | Gross: $16.64M
7. 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: 180,074 | Gross: $28.97M
8. 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.
Director: Kevin Smith | Stars: Ben Affleck, Matt Damon, Linda Fiorentino, Bud Cort
Votes: 228,502 | Gross: $30.65M
8.5/10
9. Just Looking (1999)
R | 97 min | Comedy, Drama
Finishing 8th grade in 1955 Bronx, sex-obsessed Lenny aims to see "the act of love" that summer at his aunt's in Queens where he makes friends, meets cute nurse Hedy, and learns a few things.
Director: Jason Alexander | Stars: Richard V. Licata, Marcell Rosenblatt, Ryan Merriman, Patti LuPone
Votes: 1,567 | Gross: $0.04M
10. Holy Smoke (1999)
R | 115 min | Comedy, Drama
Ruth's been brainwashed by a guru in Delhi, India. Her parents in Sydney hire a specialist in reversing this. Ruth is tricked to return to Australia and is isolated in an outback cabin with the specialist. It gets messy.
Director: Jane Campion | Stars: Kate Winslet, Harvey Keitel, Julie Hamilton, Sophie Lee
Votes: 15,639 | Gross: $1.76M
8/10
11. Arlington Road (1999)
R | 117 min | Action, Crime, Drama
A man begins to suspect his neighbors are not what they appear to be and their secrets could be deadly.
Director: Mark Pellington | Stars: Jeff Bridges, Tim Robbins, Joan Cusack, Hope Davis
Votes: 91,807 | Gross: $24.36M
12. Election (1999)
R | 103 min | Comedy, Romance
A high school teacher meets his match in an over-achieving student politician.
Director: Alexander Payne | Stars: Matthew Broderick, Reese Witherspoon, Loren Nelson, Chris Klein
Votes: 104,408 | Gross: $14.88M
13. 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: 102,378 | Gross: $50.67M
14. Grass (1999)
R | 80 min | Documentary, History
The history of the American government's war on marijuana in the 20th century.
Director: Ron Mann | Stars: Woody Harrelson, Harry J. Anslinger, George Bush, Cab Calloway
Votes: 3,628 | Gross: $0.31M
15. 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: 97,802 | Gross: $32.48M
16. 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: 240,807 | Gross: $81.30M
17. 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: 104,734 | Gross: $57.55M
18. 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: 248,592 | Gross: $206.04M
19. 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: 353,150 | Gross: $22.86M
20. Sweet and Lowdown (1999)
PG-13 | 95 min | Comedy, Drama, Music
In the 1930s, jazz guitarist Emmet Ray idolizes Django Reinhardt, faces gangsters and falls in love with a mute woman.
Director: Woody Allen | Stars: Sean Penn, Samantha Morton, Woody Allen, Ben Duncan
Votes: 36,656 | Gross: $4.20M
21. 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.
Director: Roger Kumble | Stars: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair
Votes: 204,966 | Gross: $38.77M
7.5/10
22. 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: 2,320,130 | Gross: $37.03M
23. Girl, Interrupted (1999)
R | 127 min | Biography, Drama
A directionless teenager, Susanna, is rushed to Claymoore, a mental institution, after a supposed suicide attempt. There, she befriends a group of troubled women who deeply influence her life.
Director: James Mangold | Stars: Winona Ryder, Angelina Jolie, Clea DuVall, Brittany Murphy
Votes: 210,999 | Gross: $28.87M
24. Three Kings (1999)
R | 114 min | Action, Adventure, Comedy
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: 180,357 | Gross: $60.65M
25. Payback (I) (1999)
R | 100 min | Action, Crime, Drama
After a successful heist, Porter is left for dead. Once he recovers, he seeks vengeance and wants his share of the money.
Director: Brian Helgeland | Stars: Mel Gibson, Gregg Henry, Maria Bello, David Paymer
Votes: 145,563 | Gross: $81.53M
26. The General's Daughter (1999)
R | 116 min | Crime, Drama, Mystery
When the daughter of a well-known and well-respected base commander is murdered, an undercover detective is summoned to look into the matter and finds a slew of cover-ups at West Point.
Director: Simon West | Stars: John Travolta, Madeleine Stowe, James Cromwell, Timothy Hutton
Votes: 63,773 | Gross: $102.71M
27. The Astronaut's Wife (1999)
R | 109 min | Drama, Sci-Fi, Thriller
After an explosion in space and subsequent two-minute radio-out period, two astronauts return home to their wives. Slightly it's revealed that they're not the same as they were.
Director: Rand Ravich | Stars: Charlize Theron, Johnny Depp, Joe Morton, Clea DuVall
Votes: 57,411 | Gross: $10.67M
28. 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: 1,050,179 | Gross: $293.51M
29. 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: 383,616 | Gross: $101.07M
30. 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: 73,872 | Gross: $66.38M
31. 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: 328,193 | Gross: $22.46M
32. The War Zone (1999)
R | 98 min | Drama, Thriller
An alienated teenager, saddened that he has moved away from London, must find a way to deal with a dark family secret.
Director: Tim Roth | Stars: Ray Winstone, Annabelle Apsion, Kate Ashfield, Lara Belmont
Votes: 11,175 | Gross: $0.25M
33. 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: 433,325 | Gross: $102.56M
34. Blast from the Past (1999)
PG-13 | 112 min | Comedy, Drama, Romance
A naive man comes out into the world after spending 35 years in a nuclear fallout shelter.
Director: Hugh Wilson | Stars: Brendan Fraser, Alicia Silverstone, Christopher Walken, Sissy Spacek
Votes: 71,610 | Gross: $26.49M
7/10
35. 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.
Director: David Koepp | Stars: Kevin Bacon, Zachary David Cope, Kathryn Erbe, Illeana Douglas
Votes: 87,418 | Gross: $21.13M
36. 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: 1,405,468 | Gross: $136.80M
37. Detroit Rock City (1999)
R | 95 min | Adventure, Comedy, Music
In 1978, four rebellious teenagers try to scam their way into a KISS concert.
Director: Adam Rifkin | Stars: Edward Furlong, Giuseppe Andrews, James DeBello, Sam Huntington
Votes: 41,310 | Gross: $4.22M
38. Any Given Sunday (1999)
R | 162 min | Drama, Sport
A behind-the-scenes look at the life-and-death struggles of modern-day gladiators and those who lead them.
Director: Oliver Stone | Stars: Al Pacino, Dennis Quaid, Cameron Diaz, James Woods
Votes: 125,831 | Gross: $75.53M
39. Wadd: The Life & Times of John C. Holmes (1999)
NC-17 | 105 min | Documentary, Adult, Biography
Friends, enemies, acquaintances, and family of porn star John Holmes recall their experiences with him, from his childhood to his eventual death from AIDS in 1988.
Director: Wesley Emerson | Stars: John Holmes, Linda Adrain, Bill Amerson, Denise Amerson
Votes: 947
40. Joan of Arc (1999)
TV-PG | 90 min | Adventure, Biography, Drama
Spurred by divine voices and visions, fifteenth century teen Joan d'Arc leads French forces against the English.
Stars: Leelee Sobieski, Chad Willett, Peter O'Toole, Neil Patrick Harris
Votes: 6,333
41. Brokedown Palace (1999)
PG-13 | 100 min | Drama, Mystery, Thriller
Two women are arrested for smuggling while vacationing in Thailand.
Director: Jonathan Kaplan | Stars: Claire Danes, Kate Beckinsale, Bill Pullman, Jacqueline Kim
Votes: 24,034 | Gross: $10.11M
7/10
42. 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 wreak 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: 460,293 | Gross: $155.25M
6.5/10
43. The Bone Collector (1999)
R | 118 min | Crime, Drama, Mystery
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: 184,741 | Gross: $66.52M
44. Ratcatcher (1999)
Not Rated | 94 min | Drama
A naïve young lad navigates the dirty squalid streets of 1973 Glasgow and the poor youth around him.
Director: Lynne Ramsay | Stars: Tommy Flanagan, Mandy Matthews, William Eadie, Michelle Stewart
Votes: 11,757 | Gross: $0.22M
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