Top 95 Ranked

Top Movies of 1999 Ranked

The Year Cinema Changed Forever

Explore the top rated films from a landmark year in cinema. From sci-fi classics to psychological thrillers, discover the best of thousand series movies.

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About Movies in 1999

If you ask a film scholar to name the most pivotal year in modern movie history, you will rarely hear 1972 or 1977. Instead, you will almost certainly hear 1999. It was a twelve month period that felt like a fever dream of creativity, a moment where the tectonic plates of the industry shifted and the rules of narrative were rewritten by a new generation of rebels. It was the year cinema went through a collective identity crisis, and we were all better for it.

The cultural backdrop of 1999 was defined by a creeping sense of pre-millennial tension. The world was nervous about the Y2K bug and exhausted by the glossy corporate stability of the nineties. Audiences were hungry for something that felt dangerous or real. Into this void stepped The Matrix, a film that changed action cinema forever. It did not just introduce the world to bullet time; it questioned the very nature of our reality. It suggested that the cubicle life we were all leading was a digital prison, a theme that echoed through several other masterpieces that year.

Consider Fight Club, a visceral attack on consumerism that turned Brad Pitt and Edward Norton into icons of disenfranchised rage. Or look at American Beauty, which peeled back the manicured lawns of the suburbs to show the rot underneath. Even Office Space, which failed at the box office before becoming a cult legend, captured the specific, soul crushing boredom of the turn of the century. There was a pervasive feeling that the status quo was no longer enough.

While the big studios were taking risks on dark themes, the independent scene was exploding. 1999 gave us Being John Malkovich, a movie so bizarre and original that it still defies easy categorization. We saw the rise of Paul Thomas Anderson with the sprawling, operatic Magnolia and the arrival of Sofia Coppola with The Virgin Suicides. These were not just good movies; they were the bold opening statements of filmmakers who would define the next two decades of the medium.

It was also a year of massive technical and marketing revolutions. Star Wars returned with The Phantom Menace, introducing the first fully digital main character and pushing CGI into a new era. Meanwhile, a tiny low budget experiment called The Blair Witch Project used the infant internet to trick the world into thinking its grainy footage was real, effectively birthing the found footage genre.

Film fans remember 1999 because it felt like the last year of a certain kind of innocence before the franchise era truly took over. It was a time when a studio would give a massive budget to a psychological thriller like The Sixth Sense or a twisted masterpiece like Eyes Wide Shut. It was a year where every weekend brought a movie that felt essential, challenging, and entirely new. We are still living in its shadow today.

The Complete Rankings

Based on the top picks in drafts on SnakeDrafts

See Top Ten
95
1999 in House on Haunted Hill (1999)
House on Haunted Hill
1999

An amusement park mogul offers a random group of diverse people $1 million to spend the night in a decrepit former mental institution.

Horror
1h 33m
William Malone
Geoffrey Rush, Famke Janssen, Ali Larter, Taye Diggs
94
1999 in The Bachelor (1999)
The Bachelor
1999

Jimmie is seeing his single friends get married one by one. He isn't too worried until his girlfriend Anne catches the bouquet at his friend Marco's wedding. Suddenly, his wild mustang days are numbered. He finally decides to propose to her, but he sticks his foot in his mouth and botches the proposal. Being insulted by the defeatist proposal, Anne leaves town on an assignment. After she's gone, he finds out that his recently-deceased grandfather's will stipulates that he gets nothing of a multi-million dollar fortune unless he's married by 6:05pm on his 30th birthday: tomorrow! Not being able to find Anne, Jimmie begins backtracking through his past girlfriends to find a wife.

Comedy
Romance
1h 41m
Gary Sinyor
Chris O'Donnell, Renée Zellweger, Artie Lange, Ed Asner
93
1999 in Life (1999)
Life
1999

Two men in 1930s Mississippi become friends after being sentenced to life in prison together for a crime they did not commit.

Comedy
Crime
1h 48m
Ted Demme
Eddie Murphy, Martin Lawrence, Obba Babatundé, Nick Cassavetes

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92
1999 in 8MM (1999)
8MM
1999

A small, seemingly innocuous plastic reel of film leads surveillance specialist Tom Welles down an increasingly dark and frightening path. With the help of the streetwise Max, he relentlessly follows a bizarre trail of evidence to determine the fate of a complete stranger. As his work turns into obsession, he drifts farther and farther away from his wife, family and simple life as a small-town PI.

Thriller
Crime
2h 3m
Joel Schumacher
91
1999 in The Love Letter (1999)
The Love Letter
1999

In the sleepy New England town of Loblolly By The Sea, a letter has arrived that is going to wake things up. It is a love letter - ardent, sensual... and unsigned. As the letter falls into different hands, residents of the small town to eye one another with renewed interest - wondering who it's for and who it's from. Determined to find the letter's author, Helen MacFarquhar begins a quest that will open her life to a new chapter involving two decidedly different men: George, an old friend from her past, and Johnny, a young man very much in her present. Unexpectedly, one mysterious love note has the power to unlock some startling secrets, leaving a trail of wonderful surprises as it turns an entire town upside down.

Comedy
Romance
1h 28m
Peter Chan Ho-Sun
Kate Capshaw, Blythe Danner, Ellen DeGeneres, Geraldine McEwan
90
1999 in The Bone Collector (1999)
The Bone Collector
1999

Lincoln Rhyme was the department's top homicide detective and leading expert in criminal forensics until an injury left him paralyzed, depressed, and incapable of working. But when a gruesome murder in Manhattan leaves detectives baffled, they call on Rhyme to help solve the mystery. Amelia Donaghy, a rookie cop whose quick thinking preserved a gruesome murder scene, is enlisted by Rhyme to be his on-the-scene forensics expert. With Amelia reluctantly acting as Rhyme's able-bodied go-between, the pair piece together cryptic clues the killer leaves behind at the scene of the crime, hoping to catch the grisly serial killer.

Crime
Thriller
1h 58m
Phillip Noyce
89
1999 in End of Days (1999)
End of Days
1999

Cynical bodyguard Jericho is hired by a man possessed by Satan, who is in search of his bride. When Jericho realizes what is happening, he must do everything he can to save the woman and the world.

Action
Horror
2h 2m
Peter Hyams
88
1999 in Blue Streak (1999)
Blue Streak
1999

Miles Logan is a jewel thief who just hit the big time by stealing a huge diamond. However, after two years in jail, he comes to find out that he hid the diamond in a police building that was being built at the time of the robbery. In an attempt to regain his diamond, he poses as an LAPD detective.

Action
Comedy
1h 33m
Les Mayfield
Martin Lawrence, Luke Wilson, Dave Chappelle, Peter Greene
87
1999 in Simply Irresistible (1999)
Simply Irresistible
1999

After her mother's death, mediocre chef Amanda Shelton is having trouble attracting customers to her family's restaurant. While shopping for ingredients, she is given a magical crab by mysterious Gene O'Reilly. Afterward, Amanda's dishes suddenly become excellent, inducing strong emotional reactions in everyone who eats them. Tom Bartlett, who is preparing to open his own eatery, tries her cooking and falls in love.

Comedy
Romance
1h 35m
Mark Tarlov
Sarah Michelle Gellar, Sean Patrick Flanery, Dylan Baker, Patricia Clarkson
86
1999 in The Other Sister (1999)
The Other Sister
1999

A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college.

Comedy
Drama
85
1999 in Random Hearts (1999)
Random Hearts
1999

After losing their spouses in a plane crash, an internal affairs cop and a congresswoman find each other's keys in each other's loved ones' possessions and discover that the two were having an affair.

Drama
Romance
Harrison Ford, Kristin Scott Thomas, Charles S. Dutton, Richard Jenkins
84
1999 in Inspector Gadget (1999)
Inspector Gadget
1999

John Brown is a bumbling but well-intentioned security guard who is badly injured in an explosion planned by an evil mastermind. He is taken to a laboratory, where Brenda, a leading robotics surgeon, replaces his damaged limbs with state-of-the-art gadgets and tools. Named "Inspector Gadget" by the press, John -- along with his niece, Penny, and her trusty dog, Brain -- uses his new powers to discover who was behind the explosion.

Action
Adventure
1h 18m
David Kellogg
Matthew Broderick, Rupert Everett, Joely Fisher, Michelle Trachtenberg
83
1999 in Varsity Blues (1999)
Varsity Blues
1999

In small-town Texas, high school football is a religion, 17-year-old schoolboys carry the hopes of an entire community onto the gridiron every Friday night. When star quarterback Lance Harbor suffers an injury, the Coyotes are forced to regroup under the questionable leadership of John Moxon, a second-string quarterback with a slightly irreverent approach to the game.

Comedy
Drama
1h 46m
Brian Robbins
James Van Der Beek, Amy Smart, Jon Voight, Paul Walker
82
1999 in Big Daddy (1999)
Big Daddy
1999

A lazy law school grad adopts a kid to impress his girlfriend, but everything doesn't go as planned. Now he's forced to grow up while navigating the challenges of fatherhood.

Comedy
Drama
1h 33m
Dennis Dugan
Adam Sandler, Cole Sprouse, Dylan Sprouse, Joey Lauren Adams
81
1999 in Bats (1999)
Bats
1999

Genetically mutated bats escape and it's up to a bat expert and the local sheriff to stop them.

Horror
Thriller
1h 31m
Louis Morneau
Lou Diamond Phillips, Dina Meyer, Bob Gunton, Leon
80
1999 in Message in a Bottle (1999)
Message in a Bottle
1999

A woman finds a romantic letter in a bottle washed ashore and tracks down the author, a widowed shipbuilder whose wife died tragically early. As a deep and mutual attraction blossoms, the man struggles to make peace with his past so that he can move on and find happiness.

Romance
Drama
2h 11m
Luis Mandoki
79
1999 in Mystery Men (1999)
Mystery Men
1999

When Champion City's hero Captain Amazing is kidnapped by the recently paroled supervillain Casanova Frankenstein, a trio of average, everyday superheroes -- Mr. Furious, the Shoveler and the Blue Raja -- assemble a new super team to save him.

Adventure
Fantasy
2h 1m
Kinka Usher
78
1999 in Arlington Road (1999)
Arlington Road
1999

Bedraggled college professor Michael Faraday has been vexed — and increasingly paranoid — since his wife's accidental death in a botched FBI operation. When a seemingly all-American couple set up house next door, Michael begins to suspect there’s more to them than meets the eye.

Crime
Drama
1h 57m
Mark Pellington
77
1999 in eXistenZ (1999)
eXistenZ
1999

A game designer on the run from assassins must play her latest virtual reality creation with a marketing trainee to determine if the game has been damaged.

76
1999 in The Minus Man (1999)
The Minus Man
1999

When the quiet and amiable Vann Siegert drifts into town, no one suspects the evil that lies beneath the surface. Despite his easy charm, Vann is merely a reflection of what those he encounters want him to be. Soon, as locals start to disappear, it becomes clear that an eerie subtraction is at work in the sleepy hamlet.

Drama
Thriller
1h 51m
Hampton Fancher
75
1999 in Ravenous (1999)
Ravenous
1999

After arriving at his new, remote Army outpost, Capt. John Boyd and his regiment aid a wounded frontiersman who recounts a horrifying tale of a wagon train murdered by its supposed guide – a vicious U.S. Army colonel gone rogue. Fearing the worst, the regiment heads out into the wilderness to verify the gruesome claims.

Adventure
Western
1h 41m
Antonia Bird
Guy Pearce, Robert Carlyle, David Arquette, Jeremy Davies
74
1999 in Cookie's Fortune (1999)
Cookie's Fortune
1999

Conflict arises in the small town of Holly Springs when an old woman's death causes a variety of reactions among family and friends.

Comedy
Drama
73
1999 in Anywhere but Here (1999)
Anywhere but Here
1999

Single mother Adele August is bad with money, and even worse when it comes to making decisions. Her straight-laced daughter, Ann, is a successful high school student with Ivy League aspirations. When Adele decides to pack up and move the two of them from the Midwest to Beverly Hills, Calif., to pursue her dreams of Hollywood success, Ann grows frustrated with her mother's irresponsible and impulsive ways.

Drama
Comedy
1h 54m
Wayne Wang
Susan Sarandon, Natalie Portman, Hart Bochner, Eileen Ryan
72
1999 in Wing Commander (1999)
Wing Commander
1999

In the mid-27th century, the Terran Confederation is at war with the vicious alien Kilrathi Empire. When the Kilrathi capture a crucial navigational device that could lead them to Earth, the Confederation’s only hope rests with a small group of young fighter pilots. Lieutenant Christopher Blair, along with his wingman Todd 'Maniac' Marshall and Commander Jeanette 'Angel' Deveraux, must intercept the alien fleet and prevent the destruction of mankind. Battling overwhelming odds and racing against time, they face not only external threats but also inner fears and rivalries as they fight to save Earth from annihilation.

Science Fiction
Action
1h 40m
Christopher Roberts
Freddie Prinze Jr., Saffron Burrows, Matthew Lillard, Tchéky Karyo
71
1999 in The Muse (1999)
The Muse
1999

With his career on the skids, a Hollywood screenwriter enlists the aid of a modern-day muse, who proves to test his patience.

Fantasy
Comedy
1h 37m
Albert Brooks
70
1999 in Jakob the Liar (1999)
Jakob the Liar
1999

In 1944 Poland, a Jewish shop keeper named Jakob is summoned to ghetto headquarters after being caught out after curfew. While waiting for the German Kommondant, Jakob overhears a German radio broadcast about Russian troop movements. Returned to the ghetto, the shopkeeper shares his information with a friend and then rumors fly that there is a secret radio within the ghetto.

Comedy
Drama
2h 0m
Peter Kassovitz
Robin Williams, Liev Schreiber, Hannah Taylor-Gordon, Alan Arkin
69

When the body of Army Capt. Elisabeth Campbell is found on a Georgia military base, two investigators, Warrant Officers Paul Brenner and Sara Sunhill, are ordered to solve her murder. What they uncover is anything but clear-cut. Unseemly details emerge about Campbell's life, leading to allegations of a possible military coverup of her death and the involvement of her father, Lt. Gen. Joseph Campbell.

Thriller
Mystery
1h 56m
Simon West
68
1999 in Liberty Heights (1999)
Liberty Heights
1999

This semi-autobiographical film by Barry Levinson follows various members of the Kurtzman clan, a Jewish family living in suburban Baltimore during the 1950s. As teenaged Ben completes high school, he falls for Sylvia, a black classmate, creating inevitable tensions. Meanwhile, Ben's brother, Van, attends college and becomes smitten with a mysterious woman while their father tries to maintain his burlesque business.

Drama
Adrien Brody, Ben Foster, Orlando Jones, Bebe Neuwirth
67
1999 in Tea with Mussolini (1999)
Tea with Mussolini
1999

In 1930s fascist Italy, adolescent Luca just lost his mother. His father, a callous businessman, sends him to be taken care of by British expatriate Mary Wallace. Mary and her cultured friends - including artist Arabella, young widow Elsa, and archaeologist Georgie - keep a watchful eye over the boy. But the women's cultivated lives take a dramatic turn when Allied forces declare war on Mussolini.

Comedy
Drama
1h 57m
Franco Zeffirelli
Maggie Smith, Judi Dench, Joan Plowright, Cher
66
1999 in An Ideal Husband (1999)
An Ideal Husband
1999

Sir Robert Chiltern is a successful government minister, well-off and with a loving wife. All this is threatened when Mrs Cheveley appears in London with damning evidence of a past misdeed. Sir Robert turns for help to his friend Lord Goring, an apparently idle philanderer and the despair of his father. Goring knows the lady of old, and, for him, takes the whole thing pretty seriously.

Drama
Comedy
1h 37m
Oliver Parker
Cate Blanchett, Minnie Driver, Rupert Everett, Julianne Moore
65
1999 in The Haunting (1999)
The Haunting
1999

Dr. David Marrow invites three distinct individuals to the eerie and isolated Hill House to be subjects for a sleep disorder study. The unfortunate guests discover that Marrow is far more interested in the sinister mansion itself — and they soon see the true nature of its horror.

Horror
Thriller
1h 53m
Jan de Bont
64
1999 in The Deep End of the Ocean (1999)
The Deep End of the Ocean
1999

A three-year-old boy disappears during his mother's high school reunion. Nine years later, by chance, he turns up in the town in which the family has just relocated.

Drama
Mystery
1h 46m
Ulu Grosbard
Michelle Pfeiffer, Treat Williams, Jonathan Jackson, Ryan Merriman
63
1999 in A Map of the World (1999)
A Map of the World
1999

School nurse Alice Goodwin lives with her husband and two daughters on a dairy farm in a small Wisconsin community. After an accident on her property involving a friend's child, the town turns against her and Alice finds herself fighting charges of child abuse.

Drama
2h 5m
Scott Elliott
Sigourney Weaver, Julianne Moore, David Strathairn, Arliss Howard
62
1999 in Snow Falling on Cedars (1999)
Snow Falling on Cedars
1999

In the 1950s, a Japanese-American fisherman is suspected of killing his neighbour at sea. For Ishmael, a local reporter, the trial strikes a deep emotional chord when he finds his ex-lover is linked to the case. As he investigates the killing, he uncovers some startling clues that lead him to a shocking discovery.

Drama
Romance
2h 7m
Scott Hicks
Ethan Hawke, Youki Kudoh, Reeve Carney, Anne Suzuki
61
1999 in The Mummy (1999)
The Mummy
1999

Dashing legionnaire Rick O'Connell stumbles upon the hidden ruins of Hamunaptra while in the midst of a battle to claim the area in 1920s Egypt. It has been over three thousand years since former High Priest Imhotep suffered a fate worse than death as a punishment for a forbidden love—along with a curse that guarantees eternal doom upon the world if he is ever awoken.

Adventure
Action
2h 4m
Stephen Sommers
Brendan Fraser, Rachel Weisz, John Hannah, Arnold Vosloo
60
1999 in Ride with the Devil (1999)
Ride with the Devil
1999

Ride with the Devil follows four people who are fighting for truth and justice amidst the turmoil of the American Civil War. Director Ang Lee takes us to a no man's land on the Missouri/Kansas border where a staunch loyalist, an immigrant's son, a freed slave, and a young widow form an unlikely friendship as they learn how to survive in an uncertain time. In a place without rules and redefine the meaning of bravery and honor.

Drama
War
2h 18m
Skeet Ulrich, Tobey Maguire, Jewel, Jeffrey Wright
59
1999 in Mansfield Park (1999)
Mansfield Park
1999

Fanny Price is sent to live with her wealthy relatives, the Bertrams, where she is treated poorly by most except her cousin Edmund. Her life is complicated by the arrival of the worldly Mary and Henry Crawford.

Romance
Drama
1h 52m
Patricia Rozema
Frances O'Connor, Jonny Lee Miller, Alessandro Nivola, Hannah Taylor-Gordon
58
1999 in The Limey (1999)
The Limey
1999

The Limey follows Wilson, a tough English ex-con who travels to Los Angeles to avenge his daughter's death. Upon arrival, Wilson goes to task battling Valentine and an army of L.A.'s toughest criminals, hoping to find clues and piece together what happened. After surviving a near-death beating, getting thrown from a building and being chased down a dangerous mountain road, the Englishman decides to dole out some bodily harm of his own.

Crime
Drama
Terence Stamp, Lesley Ann Warren, Luis Guzmán, Barry Newman
57
1999 in Forces of Nature (1999)
Forces of Nature
1999

Ben Holmes, a professional book-jacket blurbologist, is trying to get to Savannah for his wedding. He just barely catches the last plane, but a seagull flies into the engine as the plane is taking off. All later flights are cancelled because of an approaching hurricane, so he is forced to hitch a ride in a Geo Metro with an attractive but eccentric woman named Sara.

Romance
Comedy
1h 45m
Bronwen Hughes
56
1999 in Entrapment (1999)
Entrapment
1999

Two thieves, who travel in elegant circles, try to outsmart each other and, in the process, end up falling in love.

Romance
Drama
1h 52m
Jon Amiel
Catherine Zeta-Jones, Sean Connery, Will Patton, Maury Chaykin
55
1999 in Flawless (1999)
Flawless
1999

An ultraconservative police officer suffers a debilitating stroke and is assigned to a rehabilitative program that includes singing lessons - with the drag queen next door.

Comedy
Drama
1h 52m
Joel Schumacher
Robert De Niro, Philip Seymour Hoffman, Barry Miller, Chris Bauer
54
1999 in The End of the Affair (1999)
The End of the Affair
1999

On a rainy London night in 1946, novelist Maurice Bendrix has a chance meeting with Henry Miles, husband of his ex-mistress Sarah, who abruptly ended their affair two years before. Bendrix's obsession with Sarah is rekindled; he succumbs to his own jealousy and arranges to have her followed.

Romance
Drama
1h 42m
Neil Jordan
Ralph Fiennes, Julianne Moore, Stephen Rea, James Bolam
53
1999 in Bicentennial Man (1999)
Bicentennial Man
1999

Richard Martin buys a gift, a new NDR-114 robot. The product is named Andrew by the youngest of the family's children. "Bicentennial Man" follows the life and times of Andrew, a robot purchased as a household appliance programmed to perform menial tasks. As Andrew begins to experience emotions and creative thought, the Martin family soon discovers they don't have an ordinary robot.

Science Fiction
Drama
2h 11m
Chris Columbus
52
1999 in The World Is Not Enough (1999)
The World Is Not Enough
1999

Greed, revenge, world dominance and high-tech terrorism – it's all in a day's work for Bond, who's on a mission to protect a beautiful oil heiress from a notorious terrorist. In a race against time that culminates in a dramatic submarine showdown, Bond works to defuse the international power struggle that has the world's oil supply hanging in the balance.

Adventure
Action
2h 8m
Michael Apted
Pierce Brosnan, Sophie Marceau, Robert Carlyle, Denise Richards
51
1999 in Double Jeopardy (1999)
Double Jeopardy
1999

Libby Parsons, wrongly convicted of her husband Nick's murder, thinks he is still alive. She survives the long years in prison with two burning desires sustaining her -- finding her son and solving the mystery that destroyed her once-happy life. Standing between her and her quest, however, is her parole officer, Travis Lehman. Libby poses a challenge to the cynical officer, one that forces him to face up to his own failings while pitting him against his superior and law enforcement colleagues, as she plunges into a desperate fight for justice, survival, and revenge.

Thriller
Crime
1h 45m
Bruce Beresford
Ashley Judd, Tommy Lee Jones, Bruce Greenwood, Annabeth Gish
50
1999 in The 13th Warrior (1999)
The 13th Warrior
1999

A Muslim ambassador exiled from his homeland joins a group of Vikings, initially offended by their behavior but growing to respect them. As they travel together, they learn of a legendary evil closing in and must unite to confront this formidable force.

Adventure
History
Antonio Banderas, Diane Venora, Dennis Storhøi, Vladimir Kulich
49
1999 in The Ninth Gate (1999)
The Ninth Gate
1999

A rare book dealer finds himself at the heart of a string of paranormal events when he is hired to find the last two copies of a text, The Nine Gates of the Kingdom of Shadows, capable of summoning the Devil.

Mystery
Thriller
Johnny Depp, Frank Langella, Lena Olin, Emmanuelle Seigner
48

Anakin Skywalker, a young slave strong with the Force, is discovered on Tatooine. Meanwhile, the evil Sith have returned, enacting their plot for revenge against the Jedi.

Adventure
Action
47
1999 in Topsy-Turvy (1999)
Topsy-Turvy
1999

For nearly a decade, Gilbert and Sullivan’s collaborations have delighted the English people. But in 1884, as a London heat wave cuts into the theater trade, their latest work, "Princess Ida", receives lukewarm press. In an effort to reconcile their creative differences and drawing inspiration from Japanese culture, they went on to create the hit opera "The Mikado", one of the duo's greatest successes.

Drama
Music
2h 40m
Mike Leigh
Jim Broadbent, Allan Corduner, Timothy Spall, Lesley Manville
46
1999 in Deuce Bigalow: Male Gigolo (1999)
Deuce Bigalow: Male Gigolo
1999

Deuce Bigalow is a less than attractive, down on his luck aquarium cleaner. One day he wrecks the house of a gigolo and needs quick money to repair it. The only way he can make it is to become a gigolo himself, taking on an unusual mix of female clients. He encounters a couple of problems, though. He falls in love with one of his unusual clients, and a sleazy police officer is hot on his trail.

Comedy
Romance
1h 28m
Mike Mitchell
Rob Schneider, William Forsythe, Eddie Griffin, Arija Bareikis
45
1999 in A Midsummer Night's Dream (1999)
A Midsummer Night's Dream
1999

The lovely Hermia is to wed Demetrius, but she truly cares for Lysander. Hermia's friend, Helena, is in love with Demetrius, while other romantic entanglements abound in the woods, with married fairy rulers Titania and Oberon toying with various lovers and each other.

Fantasy
Comedy
1h 56m
Michael Hoffman
Kevin Kline, Michelle Pfeiffer, Rupert Everett, Stanley Tucci
44
1999 in Angela's Ashes (1999)
Angela's Ashes
1999

An Irish Catholic family returns to 1930s Limerick after a child's death in America. The unemployed I.R.A. veteran father struggles with poverty, prejudice, and alcoholism as the family endures harsh slum conditions.

Drama
Emily Watson, Robert Carlyle, Joe Breen, Michael Legge
43
1999 in Stir of Echoes (1999)
Stir of Echoes
1999

After being hypnotized by his sister-in-law, Tom Witzky begins seeing haunting visions of a girl's ghost and a mystery begins to unfold around her.

Horror
Mystery
1h 39m
David Koepp
Kevin Bacon, Kathryn Erbe, Illeana Douglas, Zachary David Cope
42

When diabolical genius Dr. Evil travels back in time to steal superspy Austin Powers's ‘mojo,’ Austin must return to the swingin' '60s himself - with the help of American agent, Felicity Shagwell - to stop the dastardly plan. Once there, Austin faces off against Dr. Evil's army of minions to try to save the world in his own unbelievably groovy way.

Comedy
Adventure
1h 35m
Jay Roach
Mike Myers, Heather Graham, Verne Troyer, Michael York
41

Countless wiseguy films are spoofed in this film that centers on the neuroses and angst of a powerful Mafia racketeer who suffers from panic attacks. When Paul Vitti needs help dealing with his role in the "family," unlucky shrink Dr. Ben Sobel is given just days to resolve Vitti's emotional crisis and turn him into a happy, well-adjusted gangster.

40
1999 in King of Comedy (1999)
King of Comedy
1999

Wan Tin-Sau is an actor who cannot seem to catch a break, since his only professional jobs are limited to being a movie extra. As well as being an actor, he is also the head of his village's community center.

Comedy
Drama
1h 29m
Stephen Chow
Stephen Chow, Cecilia Cheung, Karen Mok Man-Wai, Richard Ng Man-Tat
39
1999 in Tarzan (1999)
1999

Tarzan was a small orphan who was raised by an ape named Kala since he was a child. He believed that this was his family, but on an expedition Jane Porter is rescued by Tarzan. He then finds out that he's human. Now Tarzan must make the decision as to which family he should belong to...

Family
Adventure
1h 28m
Chris Buck
Tony Goldwyn, Minnie Driver, Glenn Close, Alex D. Linz
38
1999 in Not One Less (1999)
Not One Less
1999

Set in the People's Republic of China during the 1990s, the film centers on a 13-year-old substitute teacher, Wei Minzhi, in the Chinese countryside. Called in to substitute for a village teacher for one month, Wei is told not to lose any students.

Drama
1h 46m
Zhang Yimou
Wei Minzhi, Zhang Huike, Tian Zhenda, Gao Enman
37
1999 in October Sky (1999)
October Sky
1999

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.

Drama
1h 47m
Joe Johnston
36
1999 in The Boondock Saints (1999)
The Boondock Saints
1999

Tired of the crime overrunning the streets of Boston, Irish Catholic twin brothers Conner and Murphy are inspired by their faith to cleanse their hometown of evil with their own brand of zealous vigilante justice. As they hunt down and kill one notorious gangster after another, they become controversial folk heroes in the community. But Paul Smecker, an eccentric FBI agent, is fast closing in on their blood-soaked trail.

Action
Thriller
1h 48m
Troy Duffy
Willem Dafoe, Sean Patrick Flanery, Norman Reedus, David Della Rocco
35
1999 in The Hurricane (1999)
The Hurricane
1999

The story of Rubin "Hurricane" Carter, a boxer wrongly imprisoned for murder, and the people who aided in his fight to prove his innocence.

Drama
Denzel Washington, Vicellous Shannon, Deborah Kara Unger, Liev Schreiber
34
1999 in South Park: Bigger, Longer & Uncut (1999)
South Park: Bigger, Longer & Uncut
1999

In this feature film based on the hit animated series, the third graders of South Park sneak into an R-rated film by ultra-vulgar Canadian television personalities Terrance and Phillip, and emerge with expanded vocabularies that leave their parents and teachers scandalized. When outraged Americans try to censor the film, the controversy spirals into a call to wage war on Canada and Terrance and Phillip end up on death row, with the kids their only hope of rescue.

Animation
Comedy
1h 21m
Trey Parker
Trey Parker, Matt Stone, Mary Kay Bergman, Isaac Hayes
33
1999 in Go (1999)
1999

A supermarket clerk decides to step in for an absent drug dealer, setting off an explosive, comedic chain of events.

Crime
Comedy
1h 42m
Doug Liman
Sarah Polley, Timothy Olyphant, Katie Holmes, Desmond Askew
32

Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.

Drama
Romance
1h 38m
Roger Kumble
Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair
31
1999 in The Straight Story (1999)
The Straight Story
1999

Retired farmer and widower Alvin Straight learns one day that his distant brother Lyle has suffered a stroke and may not recover. Alvin is determined to make things right with Lyle while he still can, but his brother lives in Wisconsin, while Alvin is stuck in Iowa with no car and no driver's license. He then has the idea of making the trip on his old lawnmower, thus beginning a picturesque and at times deeply spiritual odyssey.

Drama
History
Richard Farnsworth, Sissy Spacek, Jane Galloway Heitz, Joseph A. Carpenter
30

Skeptical young detective Ichabod Crane gets transferred to the hamlet of Sleepy Hollow, New York, where he is tasked with investigating the decapitations of three people – murders the townsfolk attribute to a legendary specter, The Headless Horseman.

Fantasy
Thriller
Johnny Depp, Christina Ricci, Miranda Richardson, Michael Gambon
29

On the first day at his new school, Cameron instantly falls for Bianca, the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date until her ill-tempered, completely un-dateable older sister Kat goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy with a nasty reputation of his own.

Comedy
Romance
1h 37m
Gil Junger
28
1999 in Girl, Interrupted (1999)
Girl, Interrupted
1999

Set in the changing world of the late 1960s, Susanna Kaysen's prescribed "short rest" from a psychiatrist she had met only once becomes a strange, unknown journey into Alice's Wonderland, where she struggles with the thin line between normal and crazy. Susanna soon realizes how hard it is to get out once she has been committed, and she ultimately has to choose between the world of people who belong inside or the difficult world of reality outside.

Drama
2h 7m
James Mangold
Winona Ryder, Angelina Jolie, Clea DuVall, Brittany Murphy
27
1999 in Dogma (1999)
Dogma
1999

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 loophole and reenter Heaven.

Fantasy
Comedy
Ben Affleck, Matt Damon, Linda Fiorentino, Salma Hayek Pinault
26

Following the tragic death of her teenage son, Manuela travels from Madrid to Barcelona in an attempt to contact the long-estranged father the boy never knew. She reunites with an old friend, an outspoken transgender sex worker, and befriends a troubled actress and a pregnant, HIV-positive nun.

Comedy
Drama
Cecilia Roth, Marisa Paredes, Candela Peña, Antonia San Juan
25
1999 in Man on the Moon (1999)
Man on the Moon
1999

The story of the life and career of eccentric avant-garde comedian, Andy Kaufman.

Comedy
Drama
1h 58m
Miloš Forman
24

For four years, the courageous crew of the NSEA Protector — Commander Peter Quincy Taggart, Lieutenant Tawny Madison, and Doctor Lazarus — set off on a thrilling and often dangerous mission in space ... until their series was cancelled! Now, twenty years later, aliens under attack have mistaken the Galaxy Quest television transmissions for "historical documents" and beam up the crew of has-been actors to save the universe. With no script, no director, and no clue, the actors must turn in the performances of their lives.

Comedy
Science Fiction
1h 42m
Dean Parisot
23

In the small town of Rockwell, Maine in October 1957, a giant metal machine befriends a nine-year-old boy and ultimately finds its humanity by unselfishly saving people from their own fears and prejudices.

Animation
Science Fiction
1h 26m
Brad Bird
Jennifer Aniston, Harry Connick Jr., Vin Diesel, James Gammon
Why it ranks

Brad Bird’s soulful debut is a masterclass in hand-drawn artistry and Cold War subversion. It avoids the typical pitfalls of family entertainment to deliver a profound, pacifist message wrapped in silver-age sci-fi aesthetics.

22

In October of 1994 three student filmmakers disappeared in the woods near Burkittsville, Maryland, while shooting a documentary. A year later their footage was found.

Horror
Mystery
1h 21m
Daniel Myrick
Heather Donahue, Joshua Leonard, Michael C. Williams, Bob Griffin
Why it ranks

This low-budget phenomenon weaponized the power of suggestion and birthed a new aesthetic language for the horror genre. By leaning into the raw imperfections of digital video, it tapped into a primal, claustrophobic realism.

21
1999 in The Thomas Crown Affair (1999)
The Thomas Crown Affair
1999

Bored billionaire executive Thomas Crown entertains himself by stealing a Monet from a reputed museum with an elaborate diversion. When Catherine Banning, the insurance company's investigator, takes an interest in Crown, he may have met his match, and a complicated back-and-forth game with seductive undertones begins between them.

Drama
Crime
Pierce Brosnan, Rene Russo, Denis Leary, Frankie Faison
20

Once called "Father Frank" for his efforts to rescue lives, Frank Pierce sees the ghosts of those he failed to save around every turn. He has tried everything he can to get fired, calling in sick, delaying taking calls where he might have to face one more victim he couldn't help, yet cannot quit the job on his own.

19
1999 in The Cider House Rules (1999)
The Cider House Rules
1999

Homer is an orphan who was never adopted, becoming the favorite of orphanage director Dr. Larch. Dr. Larch imparts his full medical knowledge on Homer, who becomes a skilled, albeit unlicensed, physician. But Homer yearns for a self-chosen life outside the orphanage. What will Homer learn about life and love in the cider house? What of the destiny that Dr. Larch has planned for him?

18
1999 in Boys Don't Cry (1999)
Boys Don't Cry
1999

A young transgender man explores his gender identity and searches for love in rural Nebraska.

Crime
Drama
1h 58m
Kimberly Peirce
Hilary Swank, Chloë Sevigny, Peter Sarsgaard, Brendan Sexton III
17
1999 in American Pie (1999)
American Pie
1999

At a high-school party, four friends find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to all "score" by their senior prom.

Comedy
Romance
1h 35m
Paul Weitz
Jason Biggs, Chris Klein, Thomas Ian Nicholas, Alyson Hannigan
16

London bookstore owner William Thacker's quiet life turns upside down when a chance encounter with famous actress Anna Scott sparks an unlikely romance challenged by their vastly different worlds.

Romance
Comedy
2h 4m
Roger Michell
Julia Roberts, Hugh Grant, Gina McKee, Tim McInnerny
15
1999 in Bowfinger (1999)
Bowfinger
1999

On the verge of bankruptcy and desperate for his big break, aspiring filmmaker Bobby Bowfinger concocts a crazy plan to make his ultimate dream movie. Rallying a ragtag team that includes a starry-eyed ingenue, a has-been diva and a film studio gofer, he sets out to shoot a blockbuster featuring the biggest star in Hollywood, Kit Ramsey -- only without letting Ramsey know he's in the picture.

Comedy
1h 37m
Frank Oz
14
1999 in Election (1999)
Election
1999

Tracy Flick is running unopposed for this year’s high school student election. But Jim McAllister has a different plan. Partly to establish a more democratic election, and partly to satisfy some deep personal anger toward Tracy, Jim talks football player Paul Metzler to run for president as well.

Comedy
Drama
1h 43m
Alexander Payne
Matthew Broderick, Reese Witherspoon, Chris Klein, Jessica Campbell
13

A group of American soldiers stationed in Iraq at the end of the Gulf War find a map they believe will take them to a huge cache of stolen Kuwaiti gold hidden near their base, and they embark on a secret mission that's destined to change everything.

Action
Comedy
1h 54m
David O. Russell
12

A depressed white-collar worker tries hypnotherapy, only to find himself in a perpetual state of devil-may-care bliss that prompts him to start living by his own rules, and hatch a hapless attempt to embezzle money from his soul-killing employers.

Comedy
1h 30m
Mike Judge
Ron Livingston, Jennifer Aniston, David Herman, Ajay Naidu
11

Tom Ripley is a calculating young man who believes it's better to be a fake somebody than a real nobody. Opportunity knocks in the form of a wealthy U.S. shipbuilder who hires Tom to travel to Italy to bring back his playboy son, Dickie. Ripley worms his way into the idyllic lives of Dickie and his girlfriend, plunging into a daring scheme of duplicity, lies and murder.

Thriller
Crime
2h 20m
Anthony Minghella
10

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

Drama
Thriller
9

Andy heads off to Cowboy Camp, leaving his toys to their own devices. Things shift into high gear when an obsessive toy collector named Al McWhiggen, owner of Al's Toy Barn kidnaps Woody. Andy's toys mount a daring rescue mission, Buzz Lightyear meets his match and Woody has to decide where he and his heart truly belong.

Animation
Comedy
1h 32m
John Lasseter
Tom Hanks, Tim Allen, Joan Cusack, Kelsey Grammer
Why it ranks

A rare sequel that surpasses its predecessor by deepening the existential stakes of its animated world. It balances sophisticated humor with a surprisingly mature meditation on obsolescence and the passage of time.

8

A supernatural tale set on death row in a Southern prison, where gentle giant John Coffey possesses the mysterious power to heal people's ailments. When the cell block's head guard, Paul Edgecomb, recognizes Coffey's miraculous gift, he tries desperately to help stave off the condemned man's execution.

Fantasy
Drama
3h 9m
Frank Darabont
Tom Hanks, David Morse, Bonnie Hunt, Michael Clarke Duncan
Why it ranks

Frank Darabont leans into a heavy, mythological sentimentality to explore the intersections of miracle and injustice. It stands out for its deliberate pacing and its unapologetic commitment to grand-scale empathetic storytelling.

7

After Dr. Bill Harford's wife, Alice, admits to having sexual fantasies about a man she met, Bill becomes obsessed with having a sexual encounter. He discovers an underground sexual group and attends one of their meetings -- and quickly discovers that he is in over his head.

Drama
Thriller
Why it ranks

Tom Cruise weaponizes his screen idol charisma by hollowing it out, delivering a portrait of emasculated anxiety that remains the most vulnerable work of his career. He replaces his signature confidence with a haunting, slack-jawed disorientation as he wanders through a dreamscape that systematically deconstructs his alpha-male persona. It is a singular, ego-free turn that proved he could be as effective a vessel for a director's vision as he is a blockbuster star.

6

One day at work, unsuccessful puppeteer Craig finds a portal into the head of actor John Malkovich. The portal soon becomes a passion for anybody who enters its mad and controlling world of overtaking another human body.

Comedy
Drama
1h 53m
Spike Jonze
Why it ranks

Spike Jonze and Charlie Kaufman delivered a deliriously inventive exercise in surrealism that defies every narrative convention of the decade. It is a singular, neurotic exploration of identity that remains unparalleled in its creative audacity.

5

On one random day in the San Fernando Valley, a dying father, a young wife, a male caretaker, a famous lost son, a police officer in love, a boy genius, an ex-boy genius, a game show host and an estranged daughter will each become part of a dazzling multiplicity of plots, but one story.

Why it ranks

Paul Thomas Anderson crafts a sprawling, operatic mosaic of human intersecting grief and cosmic coincidence. The film’s rhythmic intensity and emotional grandiosity represent a peak of ensemble-driven directorial ambition.

4

Following an unexpected tragedy, child psychologist Malcolm Crowe meets a nine year old boy named Cole Sear, who is hiding a dark secret.

Why it ranks

M. Night Shyamalan masterfully revived the quiet ghost story by prioritizing atmospheric dread over cheap shocks. This film remains the gold standard for structural precision and emotional payoff in supernatural cinema.

3

Lester Burnham, a depressed suburban father in a mid-life crisis, decides to turn his hectic life around after developing an infatuation with his daughter's attractive friend.

Drama
Kevin Spacey, Annette Bening, Thora Birch, Wes Bentley
Why it ranks

Sam Mendes peels back the manicured layers of American domesticity to reveal a haunting, lyrical desperation. Its striking visual symmetry and cynical wit offered a definitive autopsy of the suburban dream.

2

A ticking-time-bomb insomniac and a slippery soap salesman channel primal male aggression into a shocking new form of therapy. Their concept catches on, with underground "fight clubs" forming in every town, until an eccentric gets in the way and ignites an out-of-control spiral toward oblivion.

Why it ranks

Aggressive, nihilistic, and dangerously stylish, David Fincher’s adaptation captures a specific pre-millennial malaise with bruising precision. It functions as a visceral critique of consumer identity and masculine fragility.

1

Set in the 22nd century, The Matrix tells the story of a computer hacker who joins a group of underground insurgents fighting the vast and powerful computers who now rule the earth.

Action
Science Fiction
2h 16m
Lana Wachowski
Why it ranks

A watershed moment in speculative fiction that marries high-concept philosophy with groundbreaking kinetic choreography. It redefined the visual vocabulary of the action genre for the digital age.

FAQ

Frequently Asked Questions

Everything you need to know about this list and SnakeDrafts

The top films of 1999 showcased a diverse range of genres, prominently featuring psychological thrillers like 'Fight Club' and 'The Sixth Sense,' sci-fi classics such as 'The Matrix,' and thought-provoking dramas including 'American Beauty' and 'Magnolia.' This variety highlights 1999 as a year of genre-blending and innovation in cinema.

Movies from 1999, like 'Being John Malkovich' and 'The Matrix,' challenged traditional storytelling by blending reality with fantasy and incorporating complex, non-linear narratives. These films influenced a generation of filmmakers to experiment with new storytelling techniques and thematic depth.

'The Matrix' is renowned for its pioneering use of special effects, particularly the innovative 'bullet time' visual effect that revolutionized action sequences. This film set a new standard for visual storytelling in the science fiction genre.

1999 featured significant works from established directors like Stanley Kubrick with 'Eyes Wide Shut' and introduced innovative visions from directors such as the Wachowskis with 'The Matrix.' The year also highlighted David Fincher's mastery in psychological thrillers with 'Fight Club.'

Many top films of 1999 explore themes of identity crisis, reality versus perception, and societal criticism. For example, 'Fight Club' and 'American Beauty' delve into psychological and societal dissatisfaction, reflecting the cultural undercurrents of the time.

'Toy Story 2' stood out as a landmark animated film in 1999, combining humor, heartwarming narratives, and cutting-edge animation technology. It reinforced Pixar's reputation as a leader in the animation industry.

Films from 1999, notably 'The Matrix' and 'Fight Club,' heavily influenced the evolution of sci-fi and psychological thriller genres by introducing darker, more complex narratives and innovative visual effects. Their impact is seen in countless movies that followed, shaping modern genre conventions.

'The Green Mile' distinguishes itself with its blend of fantasy and drama set against a poignant narrative about justice and humanity. Its emotional depth and strong performances helped it become one of the memorable films highlighting the versatility of 1999's cinematic output.
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