Best-Rated Movies from 1999

The year 1999 was an incredible time for movies, a moment that many now look back on as a golden age of filmmaking. It was a year that perfectly capped off a decade of change and innovation in cinema, delivering a wide range of films that have since become classics. From groundbreaking science fiction to deeply moving dramas and laugh-out-loud comedies, 1999 had something for everyone. It was a time when visionary directors were given the creative freedom to bring their unique stories to the big screen, resulting in a collection of films that continue to be celebrated and discussed today.

What made 1999 so special was the sheer diversity and quality of the movies released. It wasn’t just about big-budget blockbusters, although there were certainly some of those. It was also a year for independent films to shine, for international cinema to make a global impact, and for established filmmakers to produce some of their best work. The movies of 1999 pushed boundaries, challenged conventions, and left a lasting mark on popular culture. They introduced us to unforgettable characters, iconic scenes, and stories that have stood the test of time, proving that it was truly a remarkable year for the art of filmmaking.

‘October Sky’ (1999)

‘October Sky’ tells the true story of Homer Hickam, a teenager in a West Virginia coal-mining town who is inspired by the launch of Sputnik to take up rocketry against his father’s wishes. Along with his friends, he sets out to build and launch his own rockets, hoping to win a national science fair and escape the predetermined future of working in the coal mines. The film is a heartfelt and inspirational tale about pursuing one’s dreams and the clash between tradition and ambition in a small, tight-knit community.

The movie was directed by Joe Johnston and written by Lewis Colick, based on Homer Hickam’s memoir ‘Rocket Boys’. Jake Gyllenhaal stars as Homer, in one of his early leading roles, alongside Chris Cooper as his stern but loving father, John. The cast also includes Laura Dern as Miss Riley, the supportive science teacher who encourages the boys’ passion for rocketry, and Chris Owen, William Lee Scott, and Chad Lindberg as Homer’s loyal friends and fellow rocket enthusiasts.

‘Galaxy Quest’ (1999)

‘Galaxy Quest’ is a comedic science fiction film that lovingly parodies shows like ‘Star Trek’ and the devoted fan culture that surrounds them. The story follows the washed-up cast of a defunct sci-fi television series called ‘Galaxy Quest’. They now spend their days at fan conventions and store openings until a group of real aliens, who have mistaken the show’s transmissions for historical documents, arrives to ask for their help in a real intergalactic conflict.

Directed by Dean Parisot and written by David Howard and Robert Gordon, the film features an ensemble cast. Tim Allen plays Jason Nesmith, the egotistical actor who portrayed the ship’s commander. Sigourney Weaver is Gwen DeMarco, the show’s token female officer, and Alan Rickman portrays Alexander Dane, a serious Shakespearean actor who resents his famous alien role. The cast also includes Tony Shalhoub, Sam Rockwell, and Daryl Mitchell as the other former co-stars who get swept up in this unexpected adventure.

‘The Talented Mr. Ripley’ (1999)

‘The Talented Mr. Ripley’ is a psychological thriller that delves into the dark and obsessive mind of its title character. Tom Ripley is a young man struggling to make a living in 1950s New York. He is hired by a wealthy shipbuilder to travel to Italy and persuade his prodigal son, Dickie Greenleaf, to return home. Once in Italy, Tom becomes infatuated with Dickie’s lavish lifestyle and charismatic personality, and his initial mission soon takes a sinister and deadly turn as he begins to covet Dickie’s identity.

Anthony Minghella wrote and directed this gripping film, which is based on the 1955 novel of the same name by Patricia Highsmith. The movie boasts a star-studded cast, with Matt Damon in the complex role of Tom Ripley. Jude Law plays the charming and carefree Dickie Greenleaf, and Gwyneth Paltrow portrays his trusting girlfriend, Marge Sherwood. The cast is rounded out by Cate Blanchett as a wealthy socialite and Philip Seymour Hoffman as a suspicious friend of Dickie’s.

‘Office Space’ (1999)

‘Office Space’ is a satirical comedy that captures the mundane and often absurd reality of corporate office life. The film centers on Peter Gibbons, a software programmer who is completely unmotivated and fed up with his soul-crushing job at a tech company called Initech. After a hypnotherapy session goes awry, Peter adopts a new, carefree attitude and decides to stop pretending to work, which unexpectedly leads to a promotion. He and his two best friends, also disgruntled Initech employees, then hatch a plan to embezzle from the company.

Written and directed by Mike Judge, the film is based on his ‘Milton’ animated shorts. Ron Livingston stars as the perpetually unimpressed Peter Gibbons. Jennifer Aniston plays Joanna, a restaurant waitress who shares Peter’s disdain for management. The memorable supporting cast includes David Herman and Ajay Naidu as Peter’s friends, and Gary Cole as the passive-aggressive boss, Bill Lumbergh. Stephen Root also gives a standout performance as the mumbling, stapler-obsessed Milton Waddams.

‘The Insider’ (1999)

‘The Insider’ is a gripping drama based on the true story of a tobacco industry whistleblower. The film follows Lowell Bergman, a producer for the news show ’60 Minutes’, who convinces Jeffrey Wigand, a former research chemist for a major tobacco company, to appear on the show. Wigand reveals that his former employers knowingly added carcinogenic substances to their cigarettes, leading to a massive legal and corporate battle that threatens both men’s careers and personal lives.

Directed by Michael Mann, who also co-wrote the screenplay with Eric Roth, the film is an intense look at corporate corruption and the power of journalism. Al Pacino stars as the determined producer Lowell Bergman, and Russell Crowe delivers a powerful, transformative performance as the conflicted whistleblower Jeffrey Wigand. The supporting cast features Christopher Plummer as veteran journalist Mike Wallace, along with Diane Venora, Philip Baker Hall, and Lindsay Crouse.

‘Eyes Wide Shut’ (1999)

‘Eyes Wide Shut’ is a psychological drama that explores the themes of jealousy, desire, and marital insecurity. The story follows Dr. Bill Harford, a New York City doctor whose life takes a bizarre turn after his wife, Alice, confesses that she once fantasized about another man. Haunted by this revelation, Bill embarks on a night-long journey of sexual and moral discovery, which leads him to a mysterious and secretive high-society gathering.

This was the final film from legendary director Stanley Kubrick, who co-wrote the screenplay with Frederic Raphael. The film is based on the 1926 novella ‘Traumnovelle’ (‘Dream Story’) by Arthur Schnitzler. At the time of its release, the movie was notable for starring the then-married couple Tom Cruise as Dr. Bill Harford and Nicole Kidman as his wife, Alice. The film’s dreamlike and often surreal atmosphere is enhanced by its deliberate pacing and detailed cinematography.

‘The Straight Story’ (1999)

‘The Straight Story’ is a gentle and moving drama based on a true event. It tells the story of Alvin Straight, an elderly man from Iowa who learns that his estranged brother, Lyle, who lives in Wisconsin, has suffered a stroke. Because he has poor eyesight and doesn’t trust anyone to drive him, Alvin decides to make the 240-mile journey on his riding lawnmower. Along the way, he meets a variety of characters and reflects on his life and his relationship with his brother.

The film was directed by David Lynch, known for his more surreal and unconventional films, making this straightforward and heartfelt story a unique entry in his filmography. The screenplay was written by John E. Roach and Mary Sweeney. Richard Farnsworth gives a touching and Oscar-nominated performance as Alvin Straight. Sissy Spacek plays his daughter, Rose, and Harry Dean Stanton makes a brief but impactful appearance as his brother, Lyle.

‘Being John Malkovich’ (1999)

‘Being John Malkovich’ is a surreal and highly original fantasy comedy. The film centers on Craig Schwartz, a struggling puppeteer who takes a job as a file clerk on the low-ceilinged 7½ floor of a Manhattan office building. One day, he discovers a small, hidden door that leads directly into the mind of the actor John Malkovich. For fifteen minutes at a time, anyone who enters the portal can experience the world through Malkovich’s eyes, a discovery that Craig and his co-worker Maxine decide to turn into a business venture.

This inventive film was the feature debut of both director Spike Jonze and screenwriter Charlie Kaufman. John Cusack stars as the frustrated puppeteer Craig, and Cameron Diaz plays his pet-obsessed wife, Lotte. Catherine Keener portrays the sharp and manipulative Maxine, who becomes the object of both Craig’s and Lotte’s affections. The film also features a game and self-deprecating performance from John Malkovich himself, who plays a fictionalized version of his public persona.

‘Audition’ (1999)

‘Audition’ is a Japanese horror film that starts as a drama and slowly builds to a terrifying and unforgettable conclusion. The story follows Shigeharu Aoyama, a middle-aged widower who is encouraged by his son to start dating again. A friend who works as a film producer suggests they hold a fake audition for a non-existent movie to help Aoyama find a new wife. He becomes infatuated with Asami Yamazaki, a beautiful and reserved former ballerina, but as he begins to date her, he discovers she has a dark and disturbing past.

The film was directed by Takashi Miike and is based on a novel by Ryu Murakami. The screenplay was written by Daisuke Tengan. Ryo Ishibashi stars as the lonely widower Aoyama, and Eihi Shiina gives a chilling and iconic performance as the mysterious Asami. ‘Audition’ is renowned for its slow-burn narrative that lulls the audience into a false sense of security before shifting into scenes of intense psychological and graphic horror.

‘Three Kings’ (1999)

‘Three Kings’ is a war film that blends action, comedy, and political satire. Set at the end of the Persian Gulf War, the story follows four American soldiers who discover a map that they believe leads to a cache of gold stolen from Kuwait. They decide to go on a secret mission to retrieve the treasure for themselves, but their journey takes an unexpected turn when they encounter a group of Iraqi rebels and are forced to confront the moral complexities of the conflict.

The film was written and directed by David O. Russell, from a story by John Ridley. George Clooney stars as Major Archie Gates, the cynical veteran who leads the treasure hunt. Mark Wahlberg plays Sergeant Troy Barlow, a young father eager to get home, and Ice Cube is Staff Sergeant Chief Elgin, a deeply religious man. Spike Jonze co-stars as Private First Class Conrad Vig, the naive and easily influenced member of the group.

‘South Park: Bigger, Longer & Uncut’ (1999)

‘South Park: Bigger, Longer & Uncut’ is an animated musical comedy that takes the irreverent humor of the television show to the big screen. The plot is set in motion when the four main boys, Stan, Kyle, Cartman, and Kenny, sneak in to see an R-rated Canadian movie and begin to mimic its profane language. This causes outrage among the parents of South Park, who form a protest group that eventually leads to a full-blown war between the United States and Canada.

The film was directed by Trey Parker, who also co-wrote the screenplay with Matt Stone and Pam Brady. Parker and Stone voice most of the male characters, including the four boys and their families. The movie is a sharp satire of censorship, media hysteria, and moral panics, all wrapped in a series of catchy and often explicit musical numbers. One of its songs, ‘Blame Canada’, even received an Academy Award nomination for Best Original Song.

‘The Sixth Sense’ (1999)

‘The Sixth Sense’ is a supernatural thriller known for its chilling atmosphere and famous twist ending. The film tells the story of Dr. Malcolm Crowe, a child psychologist who is haunted by his failure to help a former patient. He takes on the case of Cole Sear, a troubled young boy who claims he can see and talk to dead people. As Malcolm works to help Cole understand his unusual ability, he begins to uncover the terrifying truth behind the boy’s visions.

Written and directed by M. Night Shyamalan, this film became a cultural phenomenon and established him as a major new voice in filmmaking. Bruce Willis stars as Dr. Crowe, in a departure from his usual action-hero roles. Haley Joel Osment gives a memorable and Oscar-nominated performance as the frightened but resilient Cole Sear, delivering the iconic line, “I see dead people.” Toni Collette, who also received an Oscar nomination, plays Cole’s loving and concerned mother, Lynn.

‘All About My Mother’ (1999)

‘All About My Mother’ is a Spanish drama that explores themes of love, loss, and female friendship. The film centers on Manuela, a single mother and nurse whose teenage son is tragically killed in a car accident while trying to get an autograph from his favorite actress. Overcome with grief, Manuela travels to Barcelona to find her son’s other parent, a trans woman named Lola, to tell her about the son she never knew she had. In Barcelona, Manuela reconnects with old friends and builds a new, unconventional family of women.

The film was written and directed by the acclaimed Spanish filmmaker Pedro Almodóvar. It is a heartfelt tribute to women and to classic Hollywood melodramas, particularly ‘All About Eve’. The ensemble cast is led by Cecilia Roth as Manuela. The film also features Marisa Paredes as an aging actress, Candela Peña as a pregnant nun, Antonia San Juan as a witty trans woman, and Penélope Cruz in an early role.

‘Toy Story 2’ (1999)

‘Toy Story 2’ is an animated adventure comedy and the sequel to the highly successful ‘Toy Story’. In this film, Woody is accidentally sold to a greedy toy collector named Al McWhiggin, who discovers that Woody is a valuable collectible from a 1950s television show. While Woody meets the other toys from his collection, including Jessie the cowgirl and his horse Bullseye, Buzz Lightyear and the rest of the gang from Andy’s room embark on a daring mission to rescue him before Andy gets back from summer camp.

The film was directed by John Lasseter, Lee Unkrich, and Ash Brannon. The returning voice cast includes Tom Hanks as the loyal cowboy doll Woody and Tim Allen as the heroic space ranger Buzz Lightyear. The sequel introduces several new characters, with Joan Cusack voicing the energetic and emotional Jessie, and Kelsey Grammer as the manipulative Stinky Pete the Prospector. The film was praised for its witty script, emotional depth, and stunning animation.

‘The Iron Giant’ (1999)

‘The Iron Giant’ is an animated science fiction film that has become a beloved cult classic. Set in 1957 during the height of the Cold War, the story follows a young boy named Hogarth Hughes who discovers a giant, metal-eating robot that has fallen from space. Hogarth befriends the gentle giant and tries to keep him hidden from a paranoid government agent who is determined to destroy the alien machine. The film is a touching story about friendship, identity, and the choice between being a weapon and being a hero.

The film was directed by Brad Bird, who also co-wrote the screenplay with Tim McCanlies. It is based on the 1968 novel ‘The Iron Man’ by Ted Hughes. The voice cast features Eli Marienthal as Hogarth, Jennifer Aniston as his caring mother, Annie, and Harry Connick Jr. as a beatnik artist who helps them. Vin Diesel provides the distinctive and emotional voice for the titular Iron Giant.

‘Fight Club’ (1999)

‘Fight Club’ is a dark and stylistically daring film that critiques consumer culture and modern masculinity. The story is told by an unnamed narrator, an insomniac office worker who feels trapped in his mundane life. His world is turned upside down when he meets Tyler Durden, a charismatic and anarchic soap salesman. Together, they form an underground fight club where men can vent their frustrations, but the club soon evolves into a much larger and more dangerous organization with a mysterious agenda.

Directed by David Fincher, the film is based on the 1996 novel of the same name by Chuck Palahniuk. The screenplay was written by Jim Uhls. Edward Norton plays the unreliable narrator, and Brad Pitt gives an iconic performance as the rebellious Tyler Durden. Helena Bonham Carter portrays Marla Singer, a troubled woman who becomes involved with both men. The film is known for its complex narrative, striking visuals, and a shocking twist ending that recontextualizes the entire story.

‘The Green Mile’ (1999)

‘The Green Mile’ is a fantasy drama set in a Louisiana prison during the 1930s. The story is told through the memories of Paul Edgecomb, a former death row corrections officer. He recounts his experiences with John Coffey, a towering and gentle-natured inmate who is sentenced to death for a horrific crime but possesses a mysterious and miraculous healing ability. As Paul gets to know John, he begins to question his guilt and the nature of justice and miracles.

The film was written and directed by Frank Darabont, based on the 1996 serial novel of the same name by Stephen King. Tom Hanks stars as the compassionate officer Paul Edgecomb. The late Michael Clarke Duncan received an Academy Award nomination for his powerful and moving performance as the enigmatic John Coffey. The ensemble cast also includes David Morse, Bonnie Hunt, and James Cromwell.

‘American Beauty’ (1999)

‘American Beauty’ is a satirical drama that explores themes of love, family, and personal freedom beneath the surface of suburban American life. The film centers on Lester Burnham, a middle-aged advertising executive who is going through a midlife crisis. He becomes infatuated with his teenage daughter’s best friend, quits his job, and begins to rebel against his materialistic wife and the constraints of his seemingly perfect life. His actions set off a chain of events that affects everyone around him.

The film was directed by Sam Mendes in his feature directorial debut and was written by Alan Ball. Kevin Spacey won an Academy Award for his portrayal of Lester Burnham. Annette Bening plays his ambitious and image-obsessed wife, Carolyn, and Thora Birch portrays their insecure and cynical daughter, Jane. The film also features strong supporting performances from Wes Bentley, Mena Suvari, and Chris Cooper.

‘The Matrix’ (1999)

‘The Matrix’ is a groundbreaking science fiction action film that redefined the genre for a new generation. The story follows Thomas Anderson, a computer programmer who leads a double life as a hacker named Neo. He is contacted by a mysterious group led by Morpheus, who reveals that the world Neo knows is actually a simulated reality called the Matrix, created by intelligent machines to subdue the human population. Neo is believed to be “The One,” a prophesied hero who can free humanity.

Written and directed by the Wachowskis, the film is famous for its innovative visual effects, particularly the “bullet time” technique, and its complex philosophical ideas. Keanu Reeves stars as Neo, the reluctant hero on a journey of self-discovery. Laurence Fishburne plays the wise and determined Morpheus, and Carrie-Anne Moss is the skilled and formidable Trinity. Hugo Weaving delivers a memorable performance as the menacing Agent Smith, a sentient program designed to protect the Matrix.

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