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Lost Highway (1997)
7.6/10on IMDb
Released
David Lynch splits one man into two halfway through and never explains the join. Bill Pullman's jazz musician is watched, accused and then, inside a prison cell, transformed into someone else entirely, a younger man played by Balthazar Getty, while Patricia Arquette plays both women in their lives.
In early 1997 it felt like an art-house puzzle. Now the surveillance creeping into a married couple's home looks like the first stirring of a fear that ran through the next four years of cinema: being recorded, then replaced. It is the coldest and least forgiving film here, so start elsewhere if you want answers, and come back for a mood nothing else on the list matches.
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Gattaca (1997)
7.7/10on IMDb
Released
Andrew Niccol's first feature as director imagines a world where your genes write your resume before you are born. Ethan Hawke's Vincent, an "In-Valid" in a system obsessed with genetic perfection, borrows the identity of Jude Law's Jerome to reach a job he was never meant to have, and the whole film runs on the fear of being betrayed by his own biology. Even the title is spelled from the letters of DNA's four bases.
It cost $36 million and took roughly $12.5 million in American theaters, a flop at the time. Today it plays as the calmest, most elegant film here about identity as paperwork, and the one most likely to win over a viewer who usually avoids science fiction.
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The Game (1997)
7.7/10on IMDb
Released
Michael Douglas plays Nicholas Van Orton, a cold San Francisco banker whose younger brother, Sean Penn's Conrad, gives him an odd birthday present: entry into a game whose rules keep changing until he cannot tell where it ends and his real life begins.
This is the late-1990s fear in its most expensive suit, a wealthy man discovering that his tidy, controlled world can be staged around him by people he never sees. Two years before Fight Club, David Fincher was already pulling the rug out from under a man who thought he had everything handled. The final stretch divides viewers, so judge it on the ride, which is as tense as anything Fincher has made.
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Open Your Eyes (1997)
7.7/10on IMDb
Released
Spain's Open Your Eyes (Abre los ojos), the 1997 original that Vanilla Sky later remade. Alejandro Amenábar wrote it with Mateo Gil and directed it; Eduardo Noriega plays César, a young man who seems to have everything until a car accident scars his face, after which dreams, memories and something stranger start bleeding into one another. Penélope Cruz plays Sofía, the role she went on to repeat in the 2001 Hollywood version.
If you have only seen the remake, this is the one to watch. It is leaner, less interested in pop-culture gloss and sharper on the question of whether a perfect life can be bought, which felt very 1997 and has only grown more pointed since.
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Dark City (1998)
7.5/10on IMDb
Released
Alex Proyas made the darkest and best-looking of the reality-is-fake films: a noir city where the sun never rises and a man cannot trust a single memory of his own past. It reached theaters a year before The Matrix, did poorly at the box office, and some of its sets were later used to shoot scenes of the Wachowskis' film.
Seek out the director's cut. It removes the explanatory voice-over that was added to the opening and lets the mystery unfold as intended, which makes a real difference to a film built on not knowing. Of everything here, it is the purest version of the identity panic that runs through the whole list, and the one most overdue for rediscovery.
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Perfect Blue (1998)
8.0/10on IMDb
Released
Satoshi Kon's debut feature follows Mima, a pop idol who quits singing to become an actress, while fans insist that the "real Mima" is the singer they paid for. One of them runs a website called Mima's Room, a diary written as if by Mima herself, and the film turns that idea into a nightmare about someone else taking over your identity online.
It first screened at the Fantasia festival in 1997, when most people had barely been online, and now reads less like a period piece than a forecast of internet celebrity. It is animated but strictly for adults, with violent and disturbing scenes, and its blurring of performance and reality went on to influence filmmakers such as Darren Aronofsky.
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The Truman Show (1998)
8.2/10on IMDb
Released
Peter Weir's film, from Andrew Niccol's script, imagines an insurance salesman whose entire life is a television show he does not know he is starring in. In 1998 it played as satire pushed to an absurd extreme; two decades of reality television have since made it look almost restrained.
Jim Carrey, then best known for rubber-faced comedy, won a Golden Globe for playing Truman straight, and Ed Harris won one too. The town is the real planned community of Seaside, Florida, whose pastel perfection does half the unsettling work. It is the gentlest film on this list and the best place to start for anyone unsure about the darker titles.
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Pi (1998)
7.3/10on IMDb
Released
Darren Aronofsky's debut is the most frantic film here and the one closest to a computer's-eye view of the era. A mathematician, Max Cohen, believes he is on the verge of decoding the numerical pattern beneath the stock market, and the closer he gets, the less he can tell insight from breakdown.
Made for roughly $60,000, it won the directing award at Sundance in 1998 and feels like late-night anxiety put on film. It is short, abrasive and deliberately uncomfortable to watch, but for anyone who remembers trusting the machine a little too much, or fearing it would fail, nothing on this list captures the feeling better.
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Pleasantville (1998)
7.5/10on IMDb
Released
Gary Ross's first film as director drops two modern teenagers into a black-and-white 1950s sitcom, where color starts creeping in as the residents feel things they were never written to feel. It is the most optimistic film here, a story about choosing to leave a safe, scripted world rather than being trapped in one.
The look still impresses: it was the first major Hollywood feature to go through what is now called the digital intermediate process, with around 1,700 effects shots. Pair it with The Truman Show from the same year for two very different answers to what you do when the perfect town turns out to be a set.
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Enemy of the State (1998)
7.3/10on IMDb
Released
Tony Scott's thriller makes the late-1990s fear of being watched loud, fast and expensive. Will Smith plays Robert Clayton Dean, a labor lawyer who unknowingly ends up with a videotape of a congressman's murder and finds the NSA taking his life apart to get it back. Gene Hackman's mysterious Brill, the man who helps him run, is a knowing echo of Hackman's surveillance expert in The Conversation from 1974.
Of everything here it looks the most dated in its technology and the least dated in its worries. That gap is the reason to rewatch it: the gadgets are clunky, but the idea that your whole life can be pulled up on a screen has only become more ordinary.
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Office Space (1999)
7.6/10on IMDb
Released
Mike Judge grew this out of his animated Milton shorts, and it is the comic heart of the list: no simulations, just cubicles, fluorescent lights and a job that slowly eats the week. Ron Livingston's Peter tries hypnotherapy, comes out of it no longer caring, and becomes the most relatable rebel of 1999, right up to a hapless plan to embezzle from his employers.
It took only about $12.1 million in theaters and found its audience later on home video and Comedy Central, which played it constantly. Of all the films here it has aged the least, because the meetings have not changed.
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The Matrix (1999)
8.7/10on IMDb
Released
If one film defines this list, it is this one. The Wachowskis took the nagging suspicion running through late-1990s cinema, that ordinary life might be a front, and turned it into a blockbuster about a computer hacker who learns his world is a simulation. In 1999, for anyone who spent the day staring at a monitor, the idea that the cubicle was the illusion landed hard.
It won all four Oscars it was nominated for, including visual effects and film editing, and its action style was copied for a decade afterward. It still moves faster than most of its imitators, and it is the one film here that both camps, the sci-fi fans and the office escapists, tend to agree on.
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eXistenZ (1999)
6.8/10on IMDb
Released
David Cronenberg's own script about virtual reality arrived about a month after The Matrix and could hardly be more different. Here game consoles are organic, semi-living pods that plug by umbilical cord into a port in the player's spine. Jennifer Jason Leigh plays a star game designer on the run from assassins, with Jude Law as the marketing trainee who has to play her latest creation with her.
Squeamish viewers should know the body horror is constant. Everyone else gets the strangest film here and, in hindsight, the most prophetic about gaming, fandom and the nagging feeling of never being sure you have logged off.
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The Thirteenth Floor (1999)
7.0/10on IMDb
Released
The third simulated-world film of 1999 is the one most people missed. Based on Daniel F. Galouye's 1964 novel Simulacron-3 and directed by Josef Rusnak, it centers on a company that has built a computer simulation of 1937 Los Angeles, and on the dawning suspicion that the people who built it may be living inside the same kind of trick.
The Matrix overshadowed it, yet its period glamour and slow-burn mystery make it the most noir of the year's virtual-reality films. Watch it as a chaser once you have seen the big one: it asks the same question with less spectacle and more melancholy, which suits the idea better than you might expect.
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American Beauty (1999)
8.3/10on IMDb
Released
The suburban, white-collar version of the same unease: Kevin Spacey's Lester Burnham, a depressed father in a midlife crisis, stops performing the life he is supposed to want. It won Best Picture, Best Actor for Spacey and Best Original Screenplay for Alan Ball, and in 1999 it felt like the definitive verdict on American comfort.
It has aged worse than anything else here. Lester's infatuation with his daughter's teenage friend plays very differently now, and the film's own sense of revelation can feel smug next to the plain-spoken Office Space. Watch it as a document of what the era thought was daring, and of how closely awards voters shared the mood this list traces.
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Fight Club (1999)
8.8/10on IMDb
Released
David Fincher's adaptation of Chuck Palahniuk's novel is the angriest film here: an insomniac white-collar narrator and a slippery soap salesman channel their frustration into underground fight clubs, and then into something much worse. Its targets are consumerism and the hollow comforts of office life, though plenty of viewers have taken it as a manual rather than a warning.
It cost about $65 million and took roughly $38 million in American theaters before becoming a cult classic on DVD. That makes it the boldest studio gamble of 1999, and still the easiest film on this list to misread, so watch it with the satire switched on.
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Being John Malkovich (1999)
7.7/10on IMDb
Released
Spike Jonze and Charlie Kaufman, both making their first feature, found the strangest metaphor of the decade for wanting to be someone else: an unsuccessful puppeteer takes a filing job on a half-height office floor squeezed between the seventh and eighth, and finds a portal into the head of the actor John Malkovich.
It is the funniest of the identity films and the most generous with its weirdness, and it earned three Oscar nominations, for Jonze, Kaufman and Catherine Keener. Watched now, its vision of strangers lining up to live inside a famous person's life looks uncannily like the influencer era that followed.
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American Psycho (2000)
7.6/10on IMDb
Released
Mary Harron's adaptation of Bret Easton Ellis's 1991 novel makes Christian Bale's Patrick Bateman, a wealthy New York investment banker, the perfect nightmare for the end of the decade: a man so hollowed out by status that he barely exists beyond his business card. The famous card scene, colleagues comparing lettering and paper stock in a hushed panic, is as sharp a satire of office one-upmanship as any film has managed.
It premiered at Sundance in January 2000 and opened that April. It is graphic and bleakly funny, so skip it if screen violence is a dealbreaker; otherwise it is the sharpest film here about identity as a brand.
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Memento (2000)
8.4/10on IMDb
Released
Christopher Nolan's breakthrough is the identity film stripped to the bone. Guy Pearce plays Leonard, a man with short-term memory loss who cannot form new memories, hunting his wife's killer and rebuilding who he is from notes and photographs. One strand runs in reverse order in color while another moves forward in black and white, so you share his confusion scene by scene.
It premiered at Venice in September 2000 but did not reach American theaters until March 2001, and it earned Oscar nominations for its screenplay and editing. The last film of the era here, it closes the list by pointing toward the puzzle-box films of the decade that followed.
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