Many consider 1999 to be one of thegreatest years in film history. At the box office, the year produced over $7 billion in the US alone, and considering the average ticket price was just over $5, this marks an impressive total of tickets sold. Unsurprisingly,The Phantom Menacetopped the year’s highest-grossing hits, with the return to sci-fi’s greatest franchise proving much more favorable financially than with critics and audiences. Disney took home the largest market share of the year, albeit in a close-run race with Warner Bros., and the adventure genre was the most popular, despite producing less than 20% of the total films in the second-biggest genre of the year: drama.
Perhaps the saddest reflection when compared to 2025 is the sheer dominance of original screenplays, with$4.2 billion of US box office gross coming from original ideas, and just over $2 billion coming from true stories, remakes, or adaptations. Among this huge financial haul are some titles that have gone on to become unquestionable classics. So, with that in mind, here’s a look at 10 movies from the year 1999 that are now considered classics, ranked.
10’Election'
Directed by Alexander Payne
Based onTom Perrotta’s 1998 novel of the same name,Electionis a punchy black comedy following Tracy Flick (Reese Witherspoon) as she campaigns for the role of high school Class President. However, teacher Jim McAllister (Matthew Broderick) has other ideas, with the two engaging in politically charged warfare.
26 years on from the release ofElection, the movie has never felt more relevant. Soaked in the intellectual bloodshed of vicious politics,Electionis pitch-perfect in its satire, as well as flawless in its comedy. For its trouble,Electionwas nominated for an Academy Award for Best Adapted Screenplay, although the last thing this movie wanted was to be engaged in any more prize-hungry campaigns.
9’Audition'
Directed by Takashi Miike
One of the scariest films of 1999,Takashi Miike’s Audition follows a widowed man as he hatches a plan to screen for a new wife using an audition system. After assuming he’s found the perfect winner, little does the widower realize that he’s accidentally unleashed hell.
Auditionis just as frightful today as it was in 1999, which is quite the achievement considering a record number of people walked out of the film’s premiere at the Rotterdam Film Festival. One of thebest horror movies of the past 30 years,Auditionis cold and calculated in its delivery of barbaric terror, with the movie’s initial calm quickly spiraling into an unflinching atmosphere rarely achieved in cinema.
8’Eyes Wide Shut'
Directed by Stanley Kubrick
Eyes Wide Shut’s legacy derives sadly from the fact that it is the legendary directorStanley Kubrick’s last film, with the cinematic genius passing away from a heart attack just six days after showing the final cut of the filmto Warner Bros. Eyes Wide Shut follows William Hartford (Tom Cruise), a Manhattan doctor with an impeccable professional reputation, as he embarks on fulfilling his wife’s sexual fantasies in a night of passion that quickly turns sinister.
Whether or not this was the last film of the great Kubrick,Eyes Wide Shutis worthy of its high acclaim, and perhaps stands as one of the most underrated entries in the New York-born director’s filmography. A trulyone-of-a-kind movie made by a one-of-a-kind mind,Eyes Wide Shutto some feels like the culmination of a near-perfect career.The truth is that the film proves Kubrick had so much more industry-altering genius left to give.
Eyes Wide Shut
7’The Blair Witch Project'
Directed by Daniel Myrick, Eduardo Sánchez
For all ofThe Blair Witch Project’s detractors, there’s no doubting just how much the movie changed the face of horror. The groundbreaking found footage feature follows a trio of students on the hunt for a local haunted legend. As they venture further into the Maryland forest, it becomes clear this myth might be closer to reality than they expected.
Not only vitally innovative in its low-budget style,revolutionizing the horror genre,The Blair Witch Projectis also widely considered thefirst major movie marketed primarily via the internet.For the turn of the millennium, this represents the rapid shift into the online space, withBlair Witchleading the line for filmmaking. Although the movie may not have aged as well as others on this list, most cannot come close to just how importantThe Blair Witch Movieis to cinema history.
The Blair Witch Project
6’American Beauty'
Directed by Sam Mendes
1999 was a fascinating year for film, mainly for its symbolism of the cultural American zeitgeist of the time. With fears of other countries and their military power decreasing, leaving those dastardly foreign foes a thing of the past, it was time for the public to become introspective, withAmerican Beautythe perfect example of how the greatest fear of 1999 audiences was themselves.
The film followsKevin Spacey’s suburban father Lester, who, due to the mundanity of his white picket-fenced life, finds himself frustrated and looking to self-destruction. A glimmer of happiness emerges for Lester, although in the form of his daughter’s best friend, with Lester’s growing nihilism blurring the boundaries in his mind. A winner of five Oscars,American Beautyis often considered the best film of 1999, with its legacy sure to burn long into cinema’s future.
American Beauty
5’The Matrix'
Directed by The Wachowskis
One of the most well-known movies of all time,The Wachowskischanged the sci-fi game withThe Matrix. The film followsKeanu Reeves' computer hacker Neo, whose perception of life is changed forever when he is taken to a forbidden underworld that reveals a dark secret: The world as he knew it is the creation of a cyber-villain.
Many movies are described as timeless. The truth is, few truly are;The Matrixis one of those. A film so tapped into its own zeitgeist that it managed to be both culturally relevant in the late 90s and future-proof,The Matrixwill continue to be relevant for many decades to come, not just for its narrative content but also for its revolutionary filmmaking style — here’s looking at you bullet time — from the genius minds of The Wachowskis.
The Matrix
When a beautiful stranger leads computer hacker Neo to a forbidding underworld, he discovers the shocking truth–the life he knows is the elaborate deception of an evil cyber-intelligence.
4’The Iron Giant'
The Iron Giantis an animated masterpiece. The film follows nine-year-old Hogarth Hughes (Eli Marienthal), who becomes the unlikely friend of a giant alien robot from space. With the two forming a tender bond, the looming threat of a government intent on destroying the robot leads toHogarth’s heartfelt journeyto keep his new friend safe.
A politically aware tearjerker featuring a stellar set of voice performances,The Iron GiantisThe Wild Robotof its day.Brad Bird’s ability to sew universally understood, emotionally mature themes into family-friendly narratives is no better felt than in this stroke of genius, with the movie boasting ahuge “certified fresh” 96% critics' rating on review aggregatorRotten Tomatoes.
The Iron Giant
3’The Sixth Sense'
Directed by M. Night Shyamalan
The modern master of suspense,M. Night Shyamalan’s breakthrough movie is also arguably his best.The Sixth Sensefollows Philadelphia child psychologist Malcolm (Bruce Willis), who, after falling victim to a furious former patient whom he failed to help, seeks redemption through treating a young boy with similar symptoms to the disgruntled ex-patient. Little does Malcolm know, the convalescent child in his care harbors a terrifying secret.
Featuring themost famous twist in cinema history, proving 1999 to be one of the best years for surprise endings,The Sixth Senseset the blueprint for many more horror/thrillers that came after it, ushering in a new wave of the genre hinged on its ability to pull the rug from beneath its audience’s feet. Alas, even Shyamalan himself fell for this desperate attempt to recreate what would go on to prove a once-in-a-million moment, withThe Sixth Sensetruly unmatched.
The Sixth Sense
2’Toy Story 2'
Directed by John Lasseter, Ash Brannon, Lee Unkrich
One of thehighest-rated animated movies of all time,Toy Story 2returns to the world of Woody (Tom Hanks) and Buzz (Tim Allen), only this time it’s Woody’s turn to be saved. Toy-napped by a crazed collector after Woody found himself doubting his own identity, Buzz and the rest of Andy’s gang set out on a daring mission to save their friend.
Each stunning beat ofToy Story 2is note-perfect, with every line of dialogue, moment of reflection, or visual gag truly hitting the mark. After the enormous success of the groundbreaking first installment, Disney and Pixar managed the unthinkable by producing a sequel of even higher quality, also producing the blueprint for tearjerking musical moments in future projects, withJessie’s song of yearning a definite influence onUp’s iconic “Married Life” montage.
Toy Story 2
1’Fight Club'
Directed by David Fincher
Based onChuck Palahniuk’s genius novel,David Fincher’sFight Clubis the poster film for the year 1999. The movie followsEdward Norton’s unnamed narrator as he searches for meaning in a life that continues to spiral into monotonous nothing. However, a chance encounter with the enigmatic soap maker Tyler Durden (Brad Pitt) revitalizes the narrator, although all is certainly not as it seems.
Despite many of the movie’s loverstragically warping its central message, with this in fact an anti-toxic masculinity narrative that laughs in the face of capitalism,Fight Clubstill stands as a technical marvel that many have since tried to emulate and failed. Featuring unforgettable central performances, one of cinema’s greatest twists, and enough blink-and-you’ll-miss-them moments to make multiple rewatches a must,Fight Clubis unquestionably a classic.
Fight Club
NEXT:The 10 Worst Horror Movies of the Last 30 Years, Ranked
