Movies from 1999 that Have Stood the Test of Time

The final year of the 20th century was a monumental one for cinema, a time when the flickering lights of the movie theater projected stories that would define a generation and reshape the landscape of filmmaking. It was a year of bold experiments and groundbreaking technology, where established directors pushed their creative boundaries and new voices emerged with startlingly original visions. From mind-bending science fiction to poignant human dramas, the films of this year captured the anxieties and hopes of a world on the cusp of a new millennium, leaving an indelible mark on popular culture that continues to be felt today.

These films did more than just entertain audiences, they challenged perceptions and sparked conversations that are still relevant. They introduced iconic characters and unforgettable worlds, crafting narratives that were both timely and timeless. Whether through innovative special effects that set new industry standards or through quiet, character-driven stories that explored the depths of the human condition, the movies of 1999 proved to be a treasure trove of cinematic excellence. This collection of films represents a remarkable and diverse slate of storytelling, a cinematic time capsule from a year that truly had it all.

‘The Green Mile’ (1999)

This powerful film tells the story of a death row corrections officer during the Great Depression who witnesses supernatural events following the arrival of a new inmate. The narrative unfolds through the memories of the officer, now living in a retirement home, as he recounts his experiences with the enigmatic prisoner who possesses a miraculous gift. Directed by Frank Darabont, the movie features a memorable ensemble cast led by Tom Hanks and Michael Clarke Duncan.

Based on a novel by Stephen King, this fantasy drama was met with critical acclaim for its emotional depth and compelling performances. It received several Academy Award nominations, including for Best Picture and Best Supporting Actor for Michael Clarke Duncan’s breakout role. The film is often remembered for its moving story and its exploration of themes like compassion, justice, and the nature of miracles.

‘The Matrix’ (1999)

A computer hacker uncovers a shocking truth about his reality and is drawn into a rebellion against the intelligent machines that have taken over the world. He learns that the life he knows is a simulated reality created to subdue humanity. The film follows his journey as he is trained to harness his newfound abilities and becomes a legendary figure in the fight for freedom. Keanu Reeves, Laurence Fishburne, and Carrie-Anne Moss lead the cast in this groundbreaking science fiction action film.

Directed by the Wachowskis, this movie redefined the action genre with its innovative visual effects and intricate fight choreography, particularly the now-famous “bullet time” sequences. It was a massive commercial success and won four Academy Awards for its technical achievements. The film’s philosophical themes and stylish cyber-punk aesthetic have had a profound and lasting influence on filmmaking and popular culture.

‘Fight Club’ (1999)

An insomniac office worker looking for a way to change his life crosses paths with a devil-may-care soap salesman and they form an underground club with strict rules where men fight each other. This new venture soon spirals into something much more complex and dangerous, evolving into a nationwide movement with anarchic intentions. The film, directed by David Fincher, stars Brad Pitt, Edward Norton, and Helena Bonham Carter.

This cult classic is based on the novel by Chuck Palahniuk and is celebrated for its dark humor, anti-consumerist themes, and shocking plot twist. Upon its initial release, the film was a controversial and polarizing topic of discussion among critics and audiences. Over time, however, it has gained a massive following and is now considered a landmark film for its stylistic innovation and biting social commentary.

‘American Beauty’ (1999)

A suburban father and husband in the midst of a mid-life crisis decides to make some major changes in his life after becoming infatuated with his teenage daughter’s best friend. His subsequent rebellion against his mundane existence has a profound effect on his family and neighbors, leading to a series of events that are at once comedic, tragic, and poignant. The film features a stellar cast including Kevin Spacey, Annette Bening, and Thora Birch.

Directed by Sam Mendes, this dramatic film was a critical darling, praised for its sharp writing, stunning cinematography, and powerful performances. It won five Academy Awards, including Best Picture, Best Director, and Best Actor for Kevin Spacey. The movie is remembered for its satirical look at suburban life and its exploration of themes such as conformity, repression, and the search for happiness.

‘Magnolia’ (1999)

This epic drama weaves together the interconnected stories of a group of individuals living in the San Fernando Valley over a single day. The characters, who include a game show host, a police officer, a former quiz kid, and a dying patriarch, grapple with love, loss, regret, and the search for meaning in their lives. The film is known for its ambitious narrative structure and features a large ensemble cast that includes Tom Cruise, Julianne Moore, and Philip Seymour Hoffman.

Written and directed by Paul Thomas Anderson, the film was lauded by critics for its bold storytelling, emotional intensity, and masterful direction. Tom Cruise received an Academy Award nomination for Best Supporting Actor for his dynamic performance. The movie is notable for its complex characters, its use of music, and its unforgettable, surreal climax that continues to be a subject of discussion among film enthusiasts.

‘Toy Story 2’ (1999)

In this animated adventure, a beloved cowboy doll is stolen from his home by a greedy toy collector, prompting his friends to launch a daring rescue mission. While in captivity, the cowboy doll discovers his own history as a valuable collectible from a popular television show and meets other toys from his collection. The film follows his internal struggle as he must decide between returning to his owner or staying with his newfound family.

This sequel from Pixar Animation Studios was a massive critical and commercial success, with many considering it to be even better than the original. It was praised for its heartwarming story, stunning animation, and emotional depth, earning an Academy Award nomination for Best Original Song. The film is cherished for its humor, its touching exploration of friendship and loyalty, and for introducing several memorable new characters to the beloved franchise.

‘The Sixth Sense’ (1999)

A child psychologist begins treating a young boy who claims he can see and talk to the dead. Initially skeptical, the psychologist delves deeper into the boy’s terrifying world and uncovers a chilling truth that forces him to confront his own past. The film, directed by M. Night Shyamalan, is a gripping supernatural thriller starring Bruce Willis and Haley Joel Osment.

This film became a cultural phenomenon, known for its suspenseful atmosphere and one of the most famous plot twists in movie history. It was a box office sensation and received six Academy Award nominations, including for Best Picture and for Haley Joel Osment’s incredible performance. The movie’s iconic line, “I see dead people,” has become a permanent fixture in popular culture.

‘Being John Malkovich’ (1999)

An unsuccessful puppeteer discovers a hidden portal in his office building that leads directly into the mind of a famous actor, allowing him to experience life as the actor for fifteen minutes at a time. He and a coworker decide to monetize this bizarre discovery, which leads to a series of surreal and comedic complications involving identity, desire, and celebrity. The film stars John Cusack, Cameron Diaz, and Catherine Keener, with the titular actor playing a fictionalized version of himself.

Directed by Spike Jonze and written by Charlie Kaufman, this wildly original fantasy comedy was praised for its creativity, wit, and unique premise. The film earned three Academy Award nominations, including for Best Director and Best Original Screenplay. It is remembered for its bizarre humor and its thought-provoking exploration of consciousness and the nature of self.

‘All About My Mother’ (1999)

After her teenage son is tragically killed in an accident, a grieving mother travels to Barcelona to find the boy’s other parent, a transgender woman she left years ago. On her journey, she reconnects with old friends and builds a new, unconventional family of women, including a pregnant nun and a famous actress. This heartfelt drama was written and directed by acclaimed Spanish filmmaker Pedro Almodóvar.

The film was a major international success, celebrated for its vibrant characters, emotional richness, and its compassionate exploration of love, loss, and femininity. It won the Academy Award for Best Foreign Language Film and the Best Director prize at the Cannes Film Festival. The movie is considered a masterpiece of world cinema and one of its director’s most personal and beloved works.

‘The Insider’ (1999)

This gripping drama is based on the true story of a former tobacco industry executive who decides to expose the industry’s dangerous secrets on a television news program. He teams up with a determined producer to bring the story to light, and they both find themselves facing immense pressure and personal risk as powerful corporate forces try to silence them. The film, directed by Michael Mann, stars Al Pacino and Russell Crowe.

The movie was widely acclaimed by critics for its intelligent script, taut direction, and the powerful performances of its lead actors. It received seven Academy Award nominations, including for Best Picture, Best Director, and Best Actor for Russell Crowe. The film is a compelling look at corporate whistleblowing and the ethics of journalism.

‘Eyes Wide Shut’ (1999)

A wealthy New York City doctor embarks on a bizarre, night-long odyssey of sexual and moral discovery after his wife confesses that she once fantasized about another man. His journey takes him into a shadowy, secret world of masked o*gi*s and psychological danger, blurring the lines between fantasy and reality. This psychological drama was the final film from legendary director Stanley Kubrick and stars Tom Cruise and Nicole Kidman.

The film was highly anticipated and generated considerable discussion upon its release due to its explicit content and enigmatic narrative. It has since been re-evaluated by critics and is now often regarded as a complex and masterful exploration of marriage, jealousy, and desire. The movie is noted for its dreamlike atmosphere, meticulous cinematography, and its unsettling and ambiguous conclusion.

‘Three Kings’ (1999)

At the end of the Gulf War, four American soldiers discover a map that they believe will lead them to a huge cache of stolen gold hidden near their base in Iraq. They decide to go on a secret mission to retrieve the treasure for themselves, but their greedy adventure takes an unexpected turn when they encounter Iraqi civilians who are in desperate need of their help. The film stars George Clooney, Mark Wahlberg, and Ice Cube.

Directed by David O. Russell, this war film was praised for its unique visual style, its blend of action and dark comedy, and its underlying political commentary. The movie was well-received by critics for its energetic direction and its fresh take on the war genre. It is often cited as a smart and stylish film that successfully balances thrilling entertainment with a thought-provoking message.

‘Galaxy Quest’ (1999)

The cast of a once-popular but long-cancelled science fiction television show now spends their days appearing at fan conventions and store openings. Their lives take an unexpected turn when 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 war. The film features an ensemble cast including Tim Allen, Sigourney Weaver, and Alan Rickman.

This sci-fi comedy is a clever and affectionate parody of ‘Star Trek’ and its devoted fanbase. It was a hit with both critics and audiences, who praised its humor, heart, and surprisingly thrilling action sequences. Over the years, it has become a beloved cult classic, celebrated for its witty script and its genuinely touching tribute to the power of science fiction and fandom.

‘The Iron Giant’ (1999)

During the Cold War, a young boy discovers a giant, amnesiac robot that has fallen from space. The boy 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 heartwarming story about friendship and the choice to be who you want to be.

This animated film, directed by Brad Bird, was critically acclaimed upon its release but was initially a box office disappointment. It has since found a massive audience and is now widely considered to be a modern classic of animation. The movie is praised for its beautiful hand-drawn animation, its moving story, and its powerful anti-war message.

‘Office Space’ (1999)

A disenchanted software programmer who is fed up with his mind-numbing job and condescending boss decides to stop caring about his work after a hypnotherapy session goes awry. His new carefree attitude unexpectedly leads to a promotion, and he and his two best friends then hatch a plan to embezzle money from their company. The film is a satirical look at corporate culture in the late 20th century.

Written and directed by Mike Judge, this workplace comedy was a modest success at the box office but has since become a major cult classic. Its memorable characters and endlessly quotable lines about TPS reports, flair, and red staplers have made it a favorite among anyone who has ever felt frustrated with their job. The movie’s sharp satire of office life remains as relevant and hilarious today as it was upon its release.

‘The Talented Mr. Ripley’ (1999)

In the 1950s, a charming and manipulative young man is sent to Italy to retrieve a wealthy and spoiled millionaire playboy. He becomes obsessed with the playboy’s lavish lifestyle and begins to take extreme measures to assume his identity. This psychological thriller, directed by Anthony Minghella, features a star-studded cast including Matt Damon, Gwyneth Paltrow, and Jude Law.

The film was praised by critics for its stylish direction, suspenseful plot, and the complex performances of its cast, particularly Jude Law who received an Academy Award nomination for Best Supporting Actor. The movie is a tense and elegant thriller that explores themes of identity, class, and obsession against the beautiful backdrop of coastal Italy.

‘The Virgin Suicides’ (1999)

This dreamlike and melancholic film tells the story of five beautiful and enigmatic teenage sisters in a quiet suburban neighborhood in the 1970s. The story is told from the perspective of a group of neighborhood boys who were captivated by the sisters and, years later, are still trying to piece together the mystery of their lives and their tragic fates. This was the debut feature film from director Sofia Coppola.

Based on the novel by Jeffrey Eugenides, the film was acclaimed for its unique visual style, its evocative soundtrack, and its sensitive handling of adolescent angst and tragedy. It has since become a cult favorite, celebrated for its atmospheric storytelling and its poignant portrayal of memory and lost innocence. Kirsten Dunst’s performance as the most rebellious of the sisters was also highly praised.

‘Go’ (1999)

This energetic and stylish crime comedy tells the same story from three different perspectives, all revolving around a single drug deal that goes wrong over the course of one wild Christmas Eve. The intertwined stories involve a grocery store clerk trying to make some extra cash, a pair of soap opera actors caught up with a police informant, and two friends on a crazy trip to Las Vegas. The film features a large ensemble cast of young actors.

Directed by Doug Liman, the movie was praised for its clever script, fast-paced editing, and its dark sense of humor. It became a cult classic, admired for its non-linear narrative structure and its witty dialogue. The film is often seen as a fun and inventive example of independent filmmaking from the late 90s.

‘Notting Hill’ (1999)

The life of a simple London bookstore owner is turned upside down when the world’s most famous movie star walks into his shop. A chance encounter leads to an unlikely romance, but the couple must navigate the massive gap between their two very different worlds, dealing with intrusive press and the pressures of her immense fame. This romantic comedy stars Julia Roberts and Hugh Grant.

Written by Richard Curtis, the film was a massive international box office hit and was warmly received by critics. It was praised for its charming script, witty humor, and the undeniable chemistry between its two lead actors. The movie remains a beloved classic of the romantic comedy genre, known for its sweet story and memorable scenes.

‘Election’ (1999)

A dedicated and well-liked high school civics teacher finds his personal and professional life spiraling out of control when he tries to sabotage the campaign of an ambitious and overachieving student who is running for student body president. His attempts to rig the election in favor of a more popular but less qualified candidate lead to a series of darkly comedic and disastrous consequences.

Directed by Alexander Payne, this sharp and witty satirical comedy stars Matthew Broderick and Reese Witherspoon in a breakout role. The film was a critical success, earning an Academy Award nomination for Best Adapted Screenplay. It is celebrated for its clever writing and its cynical but hilarious take on politics, ambition, and morality.

‘The Blair Witch Project’ (1999)

Three student filmmakers hike into the Black Hills of Maryland to shoot a documentary about a local legend. They are never heard from again, and one year later, their camera equipment and footage are discovered. The film is presented as this “found footage,” documenting the students’ terrifying journey as they become lost in the woods and realize that they are not alone.

This independent horror film was a cultural phenomenon and a massive box office success, largely due to a groundbreaking viral marketing campaign on the internet that convinced many people the story was real. It popularized the “found footage” genre of filmmaking and proved that a low-budget movie could compete with major studio blockbusters. Its raw, documentary-style approach created a sense of realism that terrified audiences worldwide.

‘Sleepy Hollow’ (1999)

In this gothic horror film, a quirky and eccentric New York City police constable who favors scientific methods is sent to a small, remote village to investigate a series of gruesome decapitations. The townspeople believe the killer is a supernatural entity known as the Headless Horseman, a ghost of a Revolutionary War mercenary. The constable must use his wits to uncover the truth behind the legend.

Directed by Tim Burton, this visually stunning film is a dark and atmospheric adaptation of the classic short story by Washington Irving. It stars Johnny Depp and Christina Ricci and was praised for its gorgeous production design, costumes, and cinematography, winning an Academy Award for Best Art Direction. The movie is a memorable and stylish fantasy adventure.

‘Boys Don’t Cry’ (1999)

This powerful and moving drama is based on the real-life story of a young transgender man who leaves his hometown and attempts to find love and a new life in a small town in Nebraska. He befriends a group of locals and falls for a young woman, but his happiness is threatened when his secret is discovered by two of his male friends, leading to a tragic and violent outcome.

The film was a critical triumph, largely due to the incredible lead performance by Hilary Swank, who underwent a dramatic physical transformation for the role. She won the Academy Award for Best Actress for her portrayal, and Chloë Sevigny was also nominated for Best Supporting Actress. The movie is an important and impactful piece of filmmaking that brought mainstream attention to transgender issues.

‘Cruel Intentions’ (1999)

Two wealthy and manipulative step-siblings in Manhattan make a cynical wager. The cunning and promiscuous young man is challenged by his stepsister to seduce the virtuous daughter of the new headmaster at their elite prep school. If he fails, she gets his vintage sports car, but if he succeeds, he gets to have her. The film is a modern-day adaptation of the 18th-century novel ‘Les Liaisons Dangereuses’.

This teen drama was a box office success and became a cult classic among young audiences for its stylish aesthetic, sharp dialogue, and memorable soundtrack. It features a notable cast of young stars including Sarah Michelle Gellar, Ryan Phillippe, and Reese Witherspoon. The film is remembered for its dark and daring take on teen romance and its provocative exploration of sexuality and betrayal.

‘Topsy-Turvy’ (1999)

This biographical drama chronicles the creative partnership between the famous comic opera writers Gilbert and Sullivan during a period of creative crisis in the 1880s. After their latest work receives a lukewarm reception, the duo’s collaboration is on the verge of collapse until a visit to a Japanese exhibition in London inspires them to write one of their greatest and most beloved works, ‘The Mikado’.

Directed by Mike Leigh, the film was widely acclaimed by critics for its meticulous attention to historical detail, its witty script, and the fantastic performances of its cast. It won two Academy Awards for Best Costume Design and Best Makeup. The movie is a delightful and insightful look at the world of Victorian theater and the ups and downs of the creative process.

‘The Straight Story’ (1999)

Based on a true story, this gentle and moving drama follows an elderly man from Iowa who is determined to mend his relationship with his estranged, ailing brother in Wisconsin. Because he does not have a driver’s license and his eyesight is poor, he decides to make the long journey on his riding lawnmower. The film chronicles his slow and steady trip across the American heartland and the people he meets along the way.

Directed by David Lynch, this film is a notable departure from the director’s typically surreal and unsettling style. It was praised for its simplicity, sincerity, and the powerful lead performance by Richard Farnsworth, who received an Academy Award nomination for Best Actor. The movie is a beautiful and heartwarming story about family, forgiveness, and perseverance.

‘Austin Powers: The Spy Who Shagged Me’ (1999)

In this sequel to the popular spy comedy, the groovy international man of mystery returns to action when his arch-nemesis travels back in time to the 1960s to steal his “mojo,” the source of his charisma and sex appeal. The hero must also travel back in time to stop the villain’s evil plan to destroy the world while teaming up with a beautiful and capable American agent.

This over-the-top comedy, starring Mike Myers in multiple roles, was a massive box office hit, even more successful than the original film. It was embraced by audiences for its silly humor, memorable catchphrases, and its affectionate parody of 1960s spy movies. The film’s pop culture impact was significant, with its characters and jokes becoming a huge part of the cultural conversation.

‘Any Given Sunday’ (1999)

This sports drama provides a behind-the-scenes look at the high-stakes world of professional American football, focusing on a fictional team as they struggle through a difficult season. The story follows an aging, old-school coach, an ambitious young team owner, and the conflict that arises between an aging star quarterback and a talented but arrogant young rookie who takes his place.

Directed by Oliver Stone, the film features a large ensemble cast that includes Al Pacino, Cameron Diaz, and Jamie Foxx. It was praised for its realistic portrayal of the brutal, money-driven business of professional sports and for its dynamic, fast-paced game sequences. The movie is remembered for its powerful speeches, particularly the coach’s iconic locker room talk about fighting for that inch.

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

In this animated musical comedy, four young boys from a quiet mountain town get into trouble after sneaking in to see an R-rated Canadian movie full of foul language. Their parents are outraged and form a protest group that eventually leads to the United States declaring war on Canada. It is up to the four boys to stop the war and save the world from destruction.

Based on the popular and controversial television show, this movie was a critical and commercial success. It was praised for its sharp satire, clever songwriting, and its surprisingly thoughtful defense of free speech. The film even earned an Academy Award nomination for Best Original Song for its catchy and profane ballad.

‘The Mummy’ (1999)

In the 1920s, an American adventurer serving in the French Foreign Legion teams up with a clumsy but brilliant Egyptologist and her brother on an archaeological dig in the ancient city of Hamunaptra. They accidentally awaken a cursed, mummified high priest who possesses immense supernatural powers and is determined to resurrect his long-lost love, unleashing a plague of terror upon Egypt.

This action-adventure film, starring Brendan Fraser and Rachel Weisz, was a huge box office hit and a crowd-pleasing summer blockbuster. It was praised for its fun, swashbuckling tone, its sense of humor, and its exciting blend of action, horror, and romance. The movie successfully revived the classic monster for a new generation and spawned a successful film franchise.

‘October Sky’ (1999)

Based on a true story, this inspiring drama is set in a small coal mining town in West Virginia in the 1950s. A teenage boy, inspired by the launch of the Sputnik satellite, decides to build his own rockets with the help of his friends, despite the disapproval of his father who wants him to follow him into the coal mines. With the encouragement of a supportive teacher, he pursues his dream of becoming a NASA engineer.

The film was well-received by critics and audiences for its heartwarming and uplifting story. It was praised for its strong performances, particularly from Jake Gyllenhaal in one of his first major roles. The movie is a touching and nostalgic look at a pivotal moment in American history and a powerful story about following your dreams.

‘She’s All That’ (1999)

A popular and seemingly perfect high school jock makes a bet with his friend that he can turn any girl at their school into the prom queen. His friend chooses a nerdy and socially awkward art student as the subject of the experiment. As he spends time with her and tries to give her a makeover, he starts to fall for her, but their budding romance is threatened when she learns about the bet.

This teen romantic comedy was a major box office success and became an iconic film for the generation of teenagers who grew up in the late 90s. It is a modern retelling of the classic play ‘Pygmalion’ and is remembered for its charming cast, which includes Freddie Prinze Jr. and Rachael Leigh Cook, and its memorable makeover sequence.

‘American Pie’ (1999)

On the eve of their high school graduation, four teenage friends make a pact to lose their virginity by prom night. The film follows their hilarious and often embarrassing attempts to achieve their goal, leading to a series of cringe-worthy and outrageous situations involving parents, parties, and a now-infamous incident with a warm apple pie.

This coming-of-age comedy was a massive box office hit and had a huge cultural impact, single-handedly reviving the teen comedy genre. Its raunchy humor and frank depiction of teenage sexuality were both controversial and wildly popular with young audiences. The film spawned a successful franchise and became a touchstone of late 90s pop culture.

’10 Things I Hate About You’ (1999)

In this clever teen romantic comedy, a popular and beautiful high school student is not allowed to date until her fiercely independent and antisocial older sister does. A new student who is interested in the younger sister pays a charming and rebellious bad boy to try and win over the abrasive older sister. The film is a modern-day adaptation of Shakespeare’s play ‘The Taming of the Shrew’.

The movie was a breakout hit, celebrated for its witty script and the fantastic chemistry of its young cast, which launched the careers of stars like Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt. It has become a beloved classic of the teen movie genre, praised for its smart dialogue, strong female characters, and memorable romantic moments.

‘The Cider House Rules’ (1999)

A young man who has spent his entire life growing up in a Maine orphanage under the tutelage of the facility’s kind and unconventional doctor decides to leave and see the world. He finds work at an apple orchard and falls in love, but his experiences and the people he meets force him to confront his own beliefs about life, love, and the rules we choose to live by.

This drama, based on the novel by John Irving, was a critical success. It received seven Academy Award nominations, winning for Best Adapted Screenplay and for Best Supporting Actor for Michael Caine’s moving performance as the orphanage director. The film is a poignant and beautifully crafted story about finding your place in the world.

‘Girl, Interrupted’ (1999)

This biographical drama tells the story of a young woman in the late 1960s who, after a supposed suicide attempt, is checked into a famous psychiatric hospital. Inside, she is diagnosed with borderline personality disorder and navigates the complex social world of her fellow patients, including a charismatic and rebellious sociopath who encourages her to defy the hospital’s authority.

The film features strong performances from its lead actresses, Winona Ryder and Angelina Jolie. Angelina Jolie’s powerful and intense portrayal of the rebellious patient earned her an Academy Award for Best Supporting Actress. The movie is a compelling and thought-provoking look at mental health and the challenges of conformity in a turbulent era.

‘The World Is Not Enough’ (1999)

In his third outing as the iconic secret agent, James Bond is assigned to protect the beautiful daughter of an assassinated oil tycoon. He soon uncovers a sinister plot by a ruthless international terrorist who cannot feel pain to seize control of the world’s oil supply by triggering a nuclear meltdown in Istanbul. The mission takes him from Spain to the Caspian Sea as he tries to stop the diabolical plan.

This installment in the long-running spy franchise was a commercial success. It features all the classic elements of the series, including exotic locations, thrilling action sequences, and high-tech gadgets. The film is also notable for featuring a prominent female villain and for giving one of its supporting characters, the tech expert Q played by Desmond Llewelyn, a heartfelt send-off.

‘Bicentennial Man’ (1999)

This science fiction drama follows the 200-year journey of a domestic android who begins to experience human emotions and creativity. Over the course of two centuries, he sets out on a quest to become fully human, facing challenges related to his identity, his relationships with the family he serves, and the very definition of what it means to be alive. The film is based on a story by Isaac Asimov.

Starring Robin Williams in the lead role, the film was praised for its ambitious story and its touching exploration of humanity and mortality. It received an Academy Award nomination for Best Makeup for its impressive work in aging the characters over many decades. The movie is a sentimental and thought-provoking look at the future of artificial intelligence.

‘Tarzan’ (1999)

This animated adventure tells the classic story of a human baby who is raised by a family of gorillas in the African jungle. As a young man, his life is turned upside down when he encounters other humans for the first time, including a beautiful and intelligent young woman who is there on an expedition with her father. He must choose between the human world and his gorilla family when the jungle is threatened.

Produced by Walt Disney Feature Animation, this film was a critical and commercial success. It was praised for its breathtaking animation, particularly the innovative “Deep Canvas” technique that allowed for stunning, three-dimensional backgrounds. The movie also won an Academy Award for Best Original Song for the memorable track performed by Phil Collins.

‘Entrapment’ (1999)

An ambitious insurance agent convinces her company to let her go undercover to trap a legendary and aging master art thief. She poses as a fellow thief to gain his trust and help him with a daring heist, but as they plan the elaborate job, the lines between their professional and personal relationship begin to blur, and it becomes unclear who is conning whom.

This stylish heist film stars Sean Connery and Catherine Zeta-Jones. It was a box office success, enjoyed by audiences for its thrilling action sequences, exotic locations, and the charismatic chemistry between its two lead actors. The movie is a fun and entertaining caper filled with suspense and clever plot twists.

‘Double Jeopardy’ (1999)

A woman is framed and wrongfully convicted for the murder of her husband. While in prison, she learns that her husband is actually still alive and that she cannot be tried for the same crime twice due to a legal principle. After she is paroled, she sets out on a relentless quest to find her husband and her young son, all while being pursued by her determined parole officer.

This suspenseful thriller, starring Ashley Judd and Tommy Lee Jones, was a major box office hit. Audiences were drawn to its high-concept premise and its empowering story of a woman seeking justice and revenge. The film is a fast-paced and exciting cat-and-mouse chase with a strong and resourceful female protagonist.

‘The Hurricane’ (1999)

This biographical drama tells the powerful true story of a middleweight boxer who was wrongfully convicted of a triple murder and spent nearly two decades in prison. The film follows his long and difficult fight for justice, aided by a teenager from Brooklyn and his Canadian foster family who become convinced of his innocence after reading his autobiography and work tirelessly to help overturn his conviction.

Denzel Washington’s incredible performance in the lead role was universally praised by critics and earned him an Academy Award nomination for Best Actor. The film is a compelling and emotional look at racial injustice and the perseverance of the human spirit in the face of overwhelming adversity.

‘Dogma’ (1999)

Two fallen angels who were banished from Heaven discover a loophole in Catholic doctrine that would allow them to re-enter, but doing so would undo all of creation and end existence. It is up to a disillusioned abortion clinic worker, who also happens to be the last living relative of Jesus Christ, to stop them, with the help of a motley crew that includes two prophets, a muse, and a 13th apostle.

Written and directed by Kevin Smith, this religious satire was one of the most controversial films of the year, sparking protests and condemnation from some religious groups. Despite the controversy, it was well-received by many critics for its witty dialogue, clever premise, and its surprisingly thoughtful exploration of faith. The film features a large ensemble cast of well-known actors.

‘Star Wars: Episode I – The Phantom Menace’ (1999)

This highly anticipated science fiction epic is the first chapter in a prequel trilogy that explores the backstory of the original classic films. It follows two Jedi Knights who are sent to negotiate a trade dispute but end up protecting a young queen and discovering a gifted young slave boy on a desert planet who they believe is the prophesied “Chosen One” who will bring balance to the Force.

Directed by George Lucas, this was one of the most hyped and financially successful films of all time. It introduced a new generation of characters and expanded the universe with new worlds and advanced digital effects. The movie’s pod-racing sequence and its climactic lightsaber duel are still regarded as standout moments of action and visual spectacle.

‘Varsity Blues’ (1999)

In a small Texas town where high school football is everything, an intelligent and academically-minded backup quarterback is forced to step into the spotlight after the star player is injured. He clashes with the team’s tyrannical and win-at-all-costs coach over the dangerous and unethical methods he uses to push his players to their limits, leading to a rebellion among the team.

This teen sports drama was a box office success and resonated with young audiences. It provided a cynical and more realistic look at the intense pressures of high school sports culture in America. The film is remembered for its memorable lines and for capturing a specific moment in late 90s teen cinema.

‘Big Daddy’ (1999)

A lazy and unmotivated law school graduate who has been coasting through life decides to adopt a five-year-old boy in a desperate attempt to prove to his ex-girlfriend that he is mature and responsible. His hilariously unconventional and irresponsible parenting methods lead to a series of comedic misadventures as he and the boy form an unlikely bond.

This comedy, starring Adam Sandler, was a massive commercial success and a huge hit with audiences. It showcased a softer and more sentimental side of the comedian’s typical persona, while still delivering the kind of silly and juvenile humor his fans loved. The film became one of the highest-grossing movies of the year.

‘The General’s Daughter’ (1999)

A military warrant officer and rape specialist is called in to investigate the murder of a prominent and respected female captain who is also the daughter of a famous and powerful general. As he and his co-investigator dig deeper into the case, they uncover a dark web of secrets, lies, and corruption within the supposedly disciplined and orderly world of the military base.

This mystery thriller, starring John Travolta, was a commercial success. It kept audiences guessing with its suspenseful plot and its many twists and turns. The film is a tense and gritty detective story that explores difficult themes within a compelling and complex murder investigation.

‘Wild Wild West’ (1999)

In this steampunk Western action comedy, two government agents in the 1870s, a charismatic gunslinger and a brilliant inventor and master of disguise, are tasked by the President to stop a diabolical and legless Confederate scientist. The villain is planning to assassinate the President using a giant, steam-powered mechanical tarantula. The film is based on a classic television series from the 1960s.

Starring Will Smith and Kevin Kline, this big-budget summer movie was a notable commercial success despite a mixed reception from critics. It is remembered for its elaborate and imaginative production design, its over-the-top action sequences, and its catchy theme song, which became a hit single for Will Smith.

‘Analyze This’ (1999)

A powerful and anxiety-ridden New York mob boss begins suffering from panic attacks. He seeks the help of a reluctant suburban psychiatrist who is about to get married, forcing the doctor to be on call 24/7 to deal with the mobster’s emotional crises. The film follows their hilarious and increasingly complicated doctor-patient relationship as the psychiatrist gets drawn deeper into the world of organized crime.

This gangster comedy, starring Robert De Niro and Billy Crystal, was a major box office hit. It was praised for its clever premise and the fantastic comedic chemistry between its two lead actors. The movie successfully poked fun at mafia movie clichés while also telling a genuinely funny story about friendship and self-discovery.

Let us know which of these 1999 classics you think has aged the best in the comments below.