Best-Rated Movies from 1999

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1999 stands out as an extraordinary era for cinema, often reminisced by many as the peak of filmmaking. It served as the climax of a decade marked by transformation and innovation in the world of movies, offering a diverse array of films that have since earned classic status. From pioneering science fiction to emotionally resonant dramas and side-splitting comedies, 1999 catered to various tastes. This was an epoch when visionary filmmakers were granted the artistic liberty to express their unique narratives on the silver screen, creating a collection of movies that remain celebrated and debated even today.

1999 stood out as an exceptional year in cinema due to the rich variety and top-notch quality of films that were released. It wasn’t merely about the big-budget blockbusters (though there were some); it was also a time when independent films found their footing, international cinema left a global imprint, and seasoned filmmakers delivered their finest works. The movies from 1999 ventured into uncharted territory, questioned existing norms, and left an indelible mark on pop culture. They introduced us to characters we’ll never forget, scenes that have become iconic, and tales that have stood the test of time, demonstrating that it was indeed a year of great significance for the craft of filmmaking.

‘October Sky’ (1999)

Titled ‘October Sky’, this movie recounts the genuine events surrounding Homer Hickam, a youngster from a West Virginia town steeped in coal mining. Intrigued by Sputnik’s launch, he defies his father’s wishes and ventures into rocketry. Joined by companions, they construct and release their homemade rockets with aspirations of triumphing at a national science fair and breaking free from the expected destiny of working in the coal mines. The movie is an emotional and motivational story that highlights the struggle between adhering to tradition versus chasing dreams within a close-knit, small community.

The film was helmed by Joe Johnston in terms of direction, with Lewis Colick responsible for its script, adapted from Homer Hickam’s autobiographical book titled ‘Rocket Boys’. Jake Gyllenhaal took on the leading role of Homer, marking one of his initial prominent performances. Chris Cooper portrayed Homer’s disciplinarian yet affectionate father, John. The ensemble also features Laura Dern as supportive science teacher Miss Riley, who fosters the boys’ enthusiasm for rocketry. Additionally, Chris Owen, William Lee Scott, and Chad Lindberg join the cast as Homer’s loyal friends and fellow rocket enthusiasts.

‘Galaxy Quest’ (1999)

‘Galaxy Quest’ is a humorous science fiction movie that playfully mimics shows like ‘Star Trek’, along with the passionate fan base associated with such series. The narrative revolves around the former cast members of a cancelled sci-fi television program, also titled ‘Galaxy Quest’. In their current life, they attend fan events and store openings. However, their routine is disrupted when a genuine alien race, who have misinterpreted the show’s broadcasts as historical records, arrives seeking assistance in a true interstellar battle.

Under Dean Parisot’s direction and penned by David Howard and Robert Gordon, this movie boasts a versatile acting crew. Tim Allen depicts Jason Nesmith, a self-absorbed actor known for his commander character on screen. Sigourney Weaver steps into the role of Gwen DeMarco, the female officer token on the show, while Alan Rickman embodies Alexander Dane, a respected Shakespearean actor who detests his well-known alien character. The crew also includes Tony Shalhoub, Sam Rockwell, and Daryl Mitchell as other former cast members caught up in this unforeseen journey.

‘The Talented Mr. Ripley’ (1999)

‘The Cunning Mr. Ripley’

This narrative unfolds as a chilling psychological thriller, exploring the complex and fixated psyche of its protagonist. The story centers around Tom Ripley, a young man grappling with life in 1950s New York City. He lands a job assigned by a wealthy shipbuilder to travel to Italy and encourage his estranged son, Dickie Greenleaf, to return home. Upon arriving in Italy, Tom develops an intense fascination for Dickie’s extravagant lifestyle and alluring personality, causing his original assignment to veer off course towards dangerous and lethal intentions as he yearns for Dickie’s very identity.

In natural and easy to read language: Anthony Minghella wrote and directed the movie, titled after Patricia Highsmith’s 1955 novel of the same name. The film features an impressive ensemble cast, with Matt Damon taking on the intricate character of Tom Ripley. Jude Law plays the affable and carefree Dickie Greenleaf, while Gwyneth Paltrow plays his loyal girlfriend, Marge Sherwood. Additionally, Cate Blanchett is seen as a wealthy socialite and Philip Seymour Hoffman portrays a suspicious friend of Dickie’s.

‘Office Space’ (1999)

In ‘Office Space,’ I found myself immersed in a satirical comedy that offers an uncanny portrayal of my own corporate office life’s monotonous and sometimes absurd aspects. The narrative revolves around me, Peter Gibbons, a disheartened software programmer, trapped in the suffocating confines of Initech, a tech company that’s slowly draining my spirit. Following an unexpected hypnotherapy session gone wrong, I embrace a new, laid-back demeanor and decide to put an end to my charade of working diligently – an unexpected move that lands me a promotion. My camaraderie with two fellow disgruntled Initech colleagues then blossoms into a daring plan to misappropriate funds from the company.

Mike Judge penned and helmed the production of this film, which is inspired by his animated ‘Milton’ series. Ron Livingston portrays Peter Gibbons, a character consistently displaying apathy, while Jennifer Aniston takes on the role of Joanna, a waitress in a restaurant who, like Peter, dislikes management. The film features a notable ensemble cast, including David Herman and Ajay Naidu as Peter’s friends, Gary Cole as the boss Bill Lumbergh, known for his passive-aggressive demeanor, and Stephen Root delivers an outstanding performance as Milton Waddams, a character who is both mumbling and fixated on staplers.

‘The Insider’ (1999)

As an avid film enthusiast, I can’t help but rave about ‘The Insider’, a nail-biting drama that unfolds the real-life tale of a tobacco industry whistleblower. This riveting narrative focuses on Lowell Bergman, a tenacious producer for the renowned news program ’60 Minutes’. In a captivating turn of events, he manages to persuade Jeffrey Wigand, a former research chemist from a significant tobacco corporation, to share his insights on the show. Wigand exposes the shocking truth that his past employers deliberately added cancer-causing agents to their cigarettes, igniting a monumental legal and corporate clash that jeopardizes both men’s careers and personal lives.

Under the direction of Michael Mann, who collaborated with Eric Roth on the script, this movie offers a gripping portrayal of corporate deceit and journalistic might. Al Pacino embodies the tenacious role of Lowell Bergman, while Russell Crowe delivers an impactful, metamorphosing act as the morally troubled informant Jeffrey Wigand. The ensemble cast includes Christopher Plummer as seasoned journalist Mike Wallace, alongside Diane Venora, Philip Baker Hall, and Lindsay Crouse.

‘Eyes Wide Shut’ (1999)

‘Eyes Wide Shut’ delves into the complexities of emotions like jealousy, longing, and marital tension. The narrative centers around Dr. Bill Harford, a New York City physician whose life undergoes an unusual shift when his wife, Alice, admits to having fantasized about another man. Deeply disturbed by this confession, Bill finds himself on a prolonged exploration of both sexual and ethical complexities, eventually uncovering himself at a clandestine and elite social event.

The last movie made by the renowned director Stanley Kubrick was under discussion here. He collaborated with Frederic Raphael on the script for this film, which is an adaptation of the 1926 novella ‘Dream Story’ by Arthur Schnitzler. When it came out, the movie drew attention because Tom Cruise and Nicole Kidman, who were married at the time, played the main characters – Dr. Bill Harford and his wife, Alice. The film creates a dreamy and frequently strange ambiance through its slow-paced narrative and meticulous cinematography.

‘The Straight Story’ (1999)

‘The Straight Story’ is a tender and emotional drama that’s inspired by real life events. It narrates the tale of Alvin Straight, an elderly gentleman from Iowa who discovers that his long-estranged sibling, Lyle, living in Wisconsin, has experienced a stroke. Since he struggles with his sight and can’t trust others to drive him, Alvin chooses to travel the 240 miles on his lawnmower instead. Throughout this journey, he encounters various individuals and contemplates his own life and his bond with his brother.

The movie was helmed by David Lynch, renowned for his dreamlike and non-traditional movies, adding an unusual twist to the simple and heartfelt narrative. This film stands out in his collection of work. The screenplay was penned by John E. Roach and Mary Sweeney. Richard Farnsworth delivers a poignant and Oscar-nominated portrayal as Alvin Straight. In the role of his daughter, Rose, we see Sissy Spacek, while Harry Dean Stanton lends a memorable short performance as Lyle, Alvin’s brother.

‘Being John Malkovich’ (1999)

‘Being John Malkovich’ is an inventive blend of surreal humor and fantasy. The story revolves around Craig Schwartz, a struggling puppeteer who lands a job as a file clerk in a unique Manhattan office. Hidden on the 7½ floor, he stumbles upon a secret door that allows entry into actor John Malkovich’s consciousness. This peculiar portal enables people to temporarily inhabit Malkovich’s mindscape for fifteen minutes each time, an intriguing discovery which Craig and his colleague Maxine decide to capitalize on as a unique business opportunity.

In this creative movie, Spike Jonze and Charlie Kaufman made their directorial and screenwriting debuts respectively. John Cusack takes on the role of Craig, a puppeteer feeling stifled, while Cameron Diaz stars as Lotte, Craig’s wife with an unusual fondness for pets. Catherine Keener portrays Maxine, a sharp and manipulative character who captures both Craig and Lotte’s affections. The film also includes a lively and self-mocking performance from John Malkovich, who embodies a fictionalized version of his public persona in the movie.

‘Audition’ (1999)

In natural and easy-to-read language, the Japanese horror film titled ‘Audition’ initially presents itself as a drama but gradually escalates into an intense and chilling climax. The narrative revolves around Shigeharu Aoyama, a middle-aged widower who is persuaded by his son to venture back into dating. His friend, a movie producer, proposes an unusual approach: they stage a fake audition for a non-existent film to aid Aoyama in finding a new partner. He develops a strong attraction towards Asami Yamazaki, a stunning yet reserved former ballerina. However, as their relationship blossoms, he uncovers her troubled and unsettling history.

The movie titled ‘Audition’ was crafted by director Takashi Miike, adapted from Ryu Murakami’s novel, with Daisuke Tengan responsible for its screenplay. In the leading roles, Ryo Ishibashi portrays the solitary widower Aoyama, while Eihi Shiina delivers a spine-tingling and memorable performance as the enigmatic Asami. ‘Audition’ is celebrated for its suspenseful storyline that deceives viewers with a calm beginning, only to abruptly transition into moments of gruesome psychological and visual terror.

‘Three Kings’ (1999)

‘Three Kings’ – a blend of action, humor, and political critique, this film is set towards the tail end of the Gulf War. It revolves around four U.S. military personnel who stumble upon a map believed to lead them to a hidden trove of gold looted from Kuwait. Driven by greed, they embark on a covert operation to secure the riches for themselves. However, their adventure takes an unanticipated twist as they cross paths with a band of Iraqi insurgents, forcing them to grapple with the moral ambiguities of the conflict.

David O. Russell wrote and directed the movie, with John Ridley contributing the initial idea. George Clooney takes on the role of Major Archie Gates, a hardened war veteran who spearheads the treasure hunt. Mark Wahlberg portrays Sergeant Troy Barlow, a young family man yearning to return home, while Ice Cube embodies Staff Sergeant Chief Elgin, a deeply religious individual. Spike Jonze appears as Private First Class Conrad Vig, a character known for his innocence and susceptibility to influence within the group.

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

‘South Park: Bigger, Longer & Uncut’ is a feature-length animated musical comedy, inspired by the popular TV series, featuring its characteristic offbeat humor. The story unfolds when the main characters, Stan, Kyle, Cartman, and Kenny, secretly watch an R-rated Canadian film and start using explicit language, causing uproar among South Park’s parents. In response, they form a protest group that escalates into a war between the United States and Canada.

The movie was crafted by Trey Parker, who collaborated with Matt Stone and Pam Brady on the script. Notably, Parker and Stone lend their voices to most of the male characters, encompassing the four boys and their families. This film is a biting parody of censorship, media frenzy, and moral outcries, presented through a sequence of memorable and sometimes provocative musical performances. One of its songs, ‘Blame Canada’, was even recognized with an Academy Award nomination for Best Original Song.

‘The Sixth Sense’ (1999)

‘The Sixth Sense’ is a chilling supernatural thriller, popular for its shocking twist finale. This movie revolves around Dr. Malcolm Crowe, a child psychologist grappling with the ghost of his past failures, as he attempts to help Cole Sear, a distraught young lad who professes he can converse with and perceive the deceased. As Malcolm guides Cole in managing this peculiar talent, he gradually uncovers the alarming reality hidden within the boy’s visions.

The movie, penned and helmed by M. Night Shyamalan, gained immense popularity and solidified him as a prominent new figure in the film industry. In a shift from his typical action roles, Bruce Willis portrays Dr. Crowe. Haley Joel Osment delivers an impactful and Academy Award-nominated performance as Cole Sear, a frightened yet resourceful character who famously says, “I can see dead people.” Toni Collette, also recognized with an Oscar nomination, takes on the role of Lynn, Cole’s caring and anxious mother.

‘All About My Mother’ (1999)

‘All About My Mother’ is a heartfelt Spanish drama that delves into the realms of love, loss, and the strong bond between women. The narrative revolves around Manuela, a resilient single mother and nurse, whose teenage son meets an unfortunate demise in a car accident while pursuing an autograph from his favorite actress. Stricken with sorrow, Manuela embarks on a journey to Barcelona to locate Lola, the trans woman who was her son’s other parent but was unknown to him. In Barcelona, Manuela rekindles old friendships and creates a unique, non-traditional family of women.

Pedro Almodóvar, a renowned Spanish director, made the movie, which is a touching homage to women and old-style Hollywood dramas, specifically ‘All About Eve’. The main cast includes Cecilia Roth as Manuela, Marisa Paredes as an aging actress, Candela Peña as a pregnant nun, Antonia San Juan as a funny trans woman, and Penélope Cruz in one of her early roles.

‘Toy Story 2’ (1999)

In ‘Toy Story 2’, we find ourselves on an animated adventure-comedy journey, serving as the sequel to the hugely popular original ‘Toy Story’. The story unfolds with Woody getting sold by mistake to a keen toy collector named Al McWhiggin, who learns that Woody is actually a rare collectible from a 1950s TV show. During his time with the other toys in McWhiggin’s collection, such as Jessie the cowgirl and her steed Bullseye, Buzz Lightyear and friends from Andy’s room launch a thrilling rescue operation to get Woody back before Andy returns from summer camp.

John Lasseter, Lee Unkrich, and Ash Brannon helmed the direction of this movie. Once again lending their voices to their beloved characters are Tom Hanks as the faithful cowboy toy Woody and Tim Allen as the valiant space adventurer Buzz Lightyear. New additions to the cast include Joan Cusack as the spirited, emotional Jessie and Kelsey Grammer as the cunning Stinky Pete the Prospector. Critics appreciated the movie’s clever dialogue, heartfelt moments, and breathtaking visual effects.

‘The Iron Giant’ (1999)

‘The Iron Giant’ – A cherished cult favorite, this animated science fiction movie revolves around a heartwarming tale set in 1957 during the peak of the Cold War. The narrative centers on Hogarth Hughes, a young lad who stumbles upon a colossal, space-traveled robot made entirely of metal, which eats other metals for sustenance. As Hogarth forms an unlikely bond with this peaceful giant, they both strive to keep him concealed from a suspicious government official eager to annihilate the extraterrestrial contraption. The movie beautifully portrays themes such as friendship, self-discovery, and the moral dilemma of deciding between acting as a weapon or being a hero.

The movie was crafted by Brad Bird, who collaborated with Tim McCanlies on its script. Originally inspired by Ted Hughes’ 1968 novel ‘The Iron Man’, it stars Eli Marienthal as Hogarth, Jennifer Aniston as his nurturing mother Annie, and Harry Connick Jr. as a bohemian artist who lends a hand. Vin Diesel contributes the powerful and emotional voice for the main character, The Iron Giant.

‘Fight Club’ (1999)

‘Fight Club’ is a bold and thought-provoking movie that takes aim at consumer culture and contemporary masculinity. The narrative unfolds from the perspective of an anonymous protagonist, a sleep-deprived office employee who senses his life lacks purpose. His routine existence undergoes a dramatic shift when he encounters Tyler Durden, a captivating and rebellious soap vendor. In partnership, they establish an illicit fighting club where men can release their pent-up anger. However, this clandestine group morphs into something much bigger and more perilous with a secretive plan lurking beneath the surface.

Under the guidance of director David Fincher, this movie adapts the 1996 novel with the same title by Chuck Palahniuk. The script was crafted by Jim Uhls. Edward Norton delivers an engrossing portrayal as the questionable narrator, while Brad Pitt’s role as Tyler Durden, a rebellious character, left an indelible mark. Helena Bonham Carter takes on the character of Marla Singer, a distressed woman who interacts with both leading characters. This film is renowned for its intricate plotline, striking imagery, and a surprising finale that reshapes the entire narrative.

‘The Green Mile’ (1999)

‘The Green Mile’ – A 1930s Louisiana Prison Tale from an Ex-Guard’s Perspective

This story unfolds in a Louisiana prison during the 1930s, as told by Paul Edgecomb, once a death row corrections officer. The narrative revolves around his relationship with John Coffey, a massive and kind-hearted inmate who was wrongfully sentenced for a heinous crime. However, John demonstrates an extraordinary and enigmatic healing power. As Paul gets acquainted with this unique prisoner, he starts to doubt John’s guilt and ponders over the concepts of justice, miracles, and their true nature.

The movie, titled similarly to a 1996 serial novel by Stephen King, was both written and directed by Frank Darabont. Tom Hanks portrays Paul Edgecomb, a sympathetic police officer, while the late Michael Clarke Duncan earned an Academy Award nomination for his captivating and emotional role as John Coffey, a mysterious character. The cast is also comprised of David Morse, Bonnie Hunt, and James Cromwell.

‘American Beauty’ (1999)

‘American Beauty’ delves into satirical drama by uncovering profound themes like love, family, and self-liberation hidden beneath the facade of suburban American culture. The narrative revolves around Lester Burnham, a middle-aged advertising man undergoing a midlife crisis, who develops an attraction for his teenage daughter’s friend. This leads him to leave his job, challenge his materialistic wife, and defy the shackles of his seemingly ideal life. His actions precipitate a series of events that impact those around him.

In this movie, Sam Mendes made his first appearance as a director of full-length films, with the screenplay penned by Alan Ball. Kevin Spacey earned an Oscar for his role depicting Lester Burnham. Annette Bening takes on the part of Carolyn, a driven and image-conscious wife, while Thora Birch plays their self-doubting and cynical daughter, Jane. The film also boasts impressive supporting roles from Wes Bentley, Mena Suvari, and Chris Cooper.

‘The Matrix’ (1999)

‘The Matrix’ represents a trailblazing sci-fi action movie that fundamentally reshaped the genre for future audiences. The narrative unfolds around Thomas Anderson, a computer whiz with a secret life as hacker Neo. He encounters an enigmatic band led by Morpheus, who discloses that the world Thomas experiences is in fact a digitized illusion called the Matrix, developed by advanced machines to control humankind. Neo is regarded as “The Chosen One,” a foretold savior who may liberate mankind.

The movie, scripted and helmed by the Wachowskis, is renowned for its groundbreaking visual effects, with the “bullet time” trick being one of its highlights, and its intricate philosophical themes. Keanu Reeves assumes the role of Neo, an initially hesitant protagonist embarking on a journey of self-realization. In this film, Laurence Fishburne portrays Morpheus, a shrewd and resolute character, while Carrie-Anne Moss brings life to Trinity, a powerful and formidable figure. Hugo Weaving delivers an impactful portrayal of Agent Smith, a terrifying AI designed to safeguard the Matrix.

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2025-08-20 21:50