History's Best Selling Movies of 1999

Revisiting 1999 presents a grand parade of movies history, marked by radical 90s attitude and millennium anticipation and enduring fan favorites. Unrivaled hits including Office Space, The Matrix, and Never Been Kissed took top honors in living rooms and storefronts alike. Master craftsmen from industry leaders like Mike Judge and The Wachowskis led the vanguard, engineering high-caliber releases that flew off store shelves and cemented lifelong fandoms. Dive into the full historical rankings below to see which standout creations won the day.

1. Office Space

   Released in 1999 by Mike Judge, 20th Century Fox

   On February 19, 1999, the world was introduced to the soul-crushing beige cubicles of Initech when the comedy 'Office Space' premiered in theaters. Written and directed by Mike Judge, the creative mind behind 'Beavis and Butt-Head' and 'King of the Hill,' the film was not an immediate box office smash. However, its release date marks the birth of a cultural phenomenon. It tapped into a wellspring of workplace ennui and quiet desperation felt by millions of white-collar workers at the height of the dot-com boom. The film's premiere unleashed a satire so sharp and relatable that it would soon become a revered cult classic and a cathartic touchstone for anyone who has ever dreamed of telling their boss exactly what they think.

2. The Matrix

   Released in 1999 by The Wachowskis, Warner Bros., Village Roadshow Pictures

   On March 31, 1999, audiences were invited to take the red pill and see how deep the rabbit-hole goes. The theatrical release of "The Matrix" was not just another sci-fi action movie premiere; it was a cultural reset. At the turn of the millennium, a time of anxiety and excitement about the future of technology and the internet, this film tapped directly into the zeitgeist. It presented a reality-bending narrative that questioned the very nature of existence, wrapped in a visually stunning package of cyberpunk aesthetics and revolutionary action choreography. Its release on this date marked the beginning of a new era in filmmaking and popular philosophy, forever changing the landscape of a generation.

3. Never Been Kissed

   Released in 1999 by Raja Gosnell, Drew Barrymore, Flower Films, 20th Century Fox

   On April 9, 1999, audiences were charmed by the release of "Never Been Kissed," a romantic comedy that became a defining film of its era. Starring and produced by Drew Barrymore, the movie premiered at the height of the teen film revival of the late 1990s, a period that also saw hits like "She's All That" and "10 Things I Hate About You." "Never Been Kissed" stood out with its uniquely endearing premise of a socially awkward copy editor who gets a second chance at high school, this time as an undercover reporter. Its release on this date cemented Barrymore's status as a rom-com queen and provided a sweet, funny, and heartfelt story that resonated deeply with anyone who ever felt like an outsider.

4. The Mummy

   Released in 1999 by Stephen Sommers, Universal Pictures

   On May 7, 1999, Universal Pictures unleashed 'The Mummy' upon North American audiences, marking the beginning of a summer blockbuster phenomenon. Far more than just another action-adventure film, this release breathed new life into the classic Universal Monsters franchise, blending thrilling action, exotic adventure, spine-tingling horror, and perfectly timed humor. Its premiere date was special not just for its record-breaking box office success, but for proving that audiences were hungry for large-scale, effects-driven escapism with a charismatic cast and a clear sense of fun. It quickly became a global sensation, setting a high bar for cinematic entertainment that summer.

5. Star Wars: Episode I – The Phantom Menace

   Released in 1999 by George Lucas, Lucasfilm Ltd., 20th Century Fox

   On May 19, 1999, the world of cinema experienced a cultural event of unprecedented scale. After a sixteen-year hiatus from the big screen, the Star Wars saga returned with the theatrical premiere of "Star Wars: Episode I – The Phantom Menace." The anticipation was a global phenomenon, with fans lining up for weeks to be the first to journey back to a galaxy far, far away. This was more than a movie release; it was a generational touchstone, the revival of a modern myth for the millions who grew up with the original trilogy and the introduction of that universe to a new legion of younger fans.

6. Austin Powers: The Spy Who Shagged Me

   Released in 1999 by Jay Roach, New Line Cinema

   June 11, 1999, marked the highly anticipated theatrical debut of 'Austin Powers: The Spy Who Shagged Me,' the uproarious sequel that solidified the Austin Powers franchise as a comedic powerhouse. Following the unexpected cult success of the original film, this follow-up arrived with significant buzz, ready to deliver more groovy gags and villainous antics. Its launch was nothing short of explosive, propelling it to become a massive box office hit and one of the highest-grossing comedies of its time. This particular Friday in June became a special date for moviegoers eager to reunite with the randy secret agent and his arch-nemesis, Dr. Evil, cementing the film's place in late 90s pop culture history.

7. Tarzan

   Released in 1999 by Chris Buck, Kevin Lima, Buena Vista Pictures Distribution

   June 18, 1999, marked the highly anticipated North American theatrical release of Disney's 'Tarzan,' an animated epic that swung into theaters and into the hearts of audiences worldwide. This date launched a critically acclaimed and commercially successful film that would go on to earn a remarkable $448.2 million globally, solidifying its place as a pivotal entry in the Disney Renaissance era. It was a film lauded for its groundbreaking animation techniques and its memorable, Oscar-winning soundtrack by Phil Collins, offering a fresh, dynamic take on the classic tale of the ape-man.

8. The Sixth Sense

   Released in 1999 by M. Night Shyamalan, Spyglass Entertainment, Hollywood Pictures

   On August 6, 1999, audiences were introduced to a film that would become a cultural touchstone and redefine the psychological thriller genre for a new generation. "The Sixth Sense," written and directed by a then-unknown M. Night Shyamalan, premiered in theaters. Released in the late summer, a period not typically known for prestige films, it became a word-of-mouth phenomenon. Its release on this date marked the arrival of a major new directorial voice and unleashed one of the most famous plot twists in cinematic history upon an unsuspecting public, forever cementing its place in pop culture and making the line "I see dead people" an instantly recognizable quote around the world.

9. American Beauty

   Released in 1999 by Sam Mendes, Alan Ball, DreamWorks Pictures

   On September 15, 1999, audiences were first introduced to the haunting, satirical, and deeply poignant world of "American Beauty." Premiering in Los Angeles and New York, the film arrived at the end of a decade defined by irony and disillusionment, perfectly encapsulating the anxieties lurking beneath the tranquil surface of American suburbia. Directed by Sam Mendes in his feature film debut, and written by Alan Ball, the movie was a cultural phenomenon, sparking countless conversations about conformity, mid-life crises, and the desperate search for meaning in a material world. Its release marked the arrival of two major new talents in Hollywood and set a new standard for dramatic filmmaking as the 20th century came to a close.

10. Fight Club

    Released in 1999 by David Fincher, Chuck Palahniuk, 20th Century Fox, Regency Enterprises

    On October 15, 1999, David Fincher's "Fight Club" premiered in the United States, unleashing a cinematic Molotov cocktail that would initially confuse critics and underperform at the box office before exploding into one of the most iconic cult films of all time. Based on Chuck Palahniuk's novel, the film's release date marks the moment a subversive, darkly comedic, and stylistically brilliant critique of consumerism and modern masculinity was unleashed upon an unsuspecting public. Its controversial themes and shocking twist ending cemented its place in film history as a generation-defining statement.

11. The World Is Not Enough

    Released in 1999 by Michael Apted, Metro-Goldwyn-Mayer/United Artists

    November 19, 1999, marked the highly anticipated world premiere of 'The World Is Not Enough' in the United Kingdom, before its wider release in North America a week later. This date ushered in the 19th installment of the iconic James Bond franchise and Pierce Brosnan's third outing as the suave British secret agent. The film's launch was met with considerable excitement, quickly demonstrating its commercial appeal by achieving significant box office success globally. Its premiere date is particularly special as it set the stage for one of the most financially successful Bond films of its era, solidifying Brosnan's tenure and the franchise's enduring popularity as it headed into a new millennium.

12. The Green Mile

    Released in 1999 by Frank Darabont, Castle Rock Entertainment, Warner Bros.

    On December 10, 1999, audiences were introduced to the profoundly moving and supernatural world of 'The Green Mile.' Directed by Frank Darabont and based on Stephen King's 1996 novel, the film's premiere was a significant cinematic event. It reunited Darabont with the works of King after their triumphant collaboration on 'The Shawshank Redemption,' creating high expectations. Set in a 1930s prison, the film arrived at the end of a decade and millennium, offering a powerful, poignant story about humanity, injustice, and miracles. Its release during the holiday season positioned it as a major awards contender and a must-see prestige picture, promising a deep emotional experience for viewers.