20 Movies That are Turning 20 in 2019

1999 was a huge year for movies – check out these turn-of-the-century classics that are celebrating their birthday this year.

This article comes from Den of Geek UK.

Sometimes there’s an exciting year at the Oscars, or there’s a genre flux that means it’s a great time for horror or costume drama or (ahem) superhero movies, but very rarely is there a year that churns out such a slate of incredible, groundbreaking, memorable films as 1999.

In fact, there were so many iconic movies released that year, there wasn’t room on the list for all of them… Sleepy Hollow, Notting Hill, The Insider, Dogma, Go, Cruel Intentions, The Mummy – the list goes on. And it would go on forever if we included them all!

But cast your mind back two decades and celebrate the 20th anniversary of these modern classics that were first released in the golden year of 1999…

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Fight Club

We know, “The first rule of Fight Club…” but 20 years later people are still talking about it as one of the greatest movies of all time. Though the studio didn’t agree when they saw the initial edit. White collar worker can’t sleep, sneaks into support groups, falls in love, makes a weird friend, starts underground boxing club, mass produces soap, accumulates Space Monkeys, becomes terrorist… They didn’t know quite what it was or how to market it – even with Brad Pitt in his prime. It initially only made $37 million of its $60 million budget, and critics were as polarized as the two main characters. The Evening Standard went as far as to call it “an inadmissible assault on personal decency.”

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It was a worrying time for director David Fincher, who had managed to gloss over Alien 3 with the success of Se7en four years earlier. Brad Pitt had been on a roll since 1994’s Interview With The Vampire and Edward Norton was fresh from his Oscar nod for the previous year’s American History X. For Helena Bonham Carter it was a chance to bust out of her realm of costume dramas. And for Chuck Palahniuk, it was the first movie adaptation of one of his novels – just think of the royalties if it went well. Thankfully, through word of mouth and pure, old-fashioned controversy, the movie quickly gathered a cult following on DVD – finally getting the attention it deserved.

The Matrix

Two words: “bullet time.” Not only did the Wachowskis’ career-defining movie blow our minds with its Baudrillard-esque assault on the very nature of reality, it also challenged expectations of special effects at the time with one of the most memorable sequences in movie history. When Neo (Keanu Reeves) reaches backwards in a gravity-defying bend to avoid the agent’s gunfire, the effect slows down the bullets and moves the camera angle around Neo at a faster speed. It has become so closely associated with the movie, “bullet time” is now a registered trademark of Warner Bros.

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Add to that the spectacular fight choreography and wire-fu from Hong Kong legend Yuen Woo-Ping, the awe-inspiring sci-fi landscapes of the world outside of The Matrix and the immersive sound design (which came away with Oscars for both its effects and editing, alongside the visual teams) and it’s no wonder the movie still holds up as a genre-defining (and changing) release. A decade after his breakthrough in Bill & Ted’s Excellent Adventure it became as career-defining for Reeves as that time he drove really fast in a bus, while the red pill/blue pill “down the rabbit hole” scene has been forever swallowed into the world of modern memes.

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The Sixth Sense

Possibly one of the most spoilered (and frequently parodied) movies of all time, director M. Night Shyamalan’s first big hit was the second highest-grossing film of the year – the first Star Wars prequel, The Phantom Menace, was its only box office menace. With Haley Joel Osment as a young boy who can “see dead people” and Bruce Willis as the damaged child psychologist trying to help him, the ending brings with it what is still one of the greatest movie twists ever and the first of a technique that would become the director’s signature move.

It went down well with audiences and critics alike, and got six nods from the Academy at the Oscars – including Best Picture, Director, Screenplay, Supporting Actor and Actress (for Toni Collette as Osment’s mother) and Editing. The Shyamalan/Willis pairing continued the following year with Unbreakable – which we now know to be the first in a trilogy that finishes with Glass.


Takashi Miike knows how to get a WTF reaction out of an audience, and Audition was the first movie from the prolific (he’s directed over 100 feature films) Japanese director that made the world stand up and really ask that question. Lulled into a false sense of security with what might be a domestic drama or cutesy rom-com prelude, the story of a widower who arranges fake movie auditions for a submissive role he believes will attract the right kind of wife (he’s kind of asking for it) gradually descends into a paranoid revenge drama and, in the unforgettable final act, a torturous bloodbath.

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Sex and death. Pleasure and pain. Freud’s in there too – of course. It’s the beginnings of the J-Horror phenomenon that became prevalent during the 2000s, boasting audience sickness and walkouts in droves. The stylish visuals and extreme violence were a prelude to Miike’s 2001 hit Ichi The Killer, which firmly cemented the director’s reputation overseas as both a maverick and master of his craft.

Toy Story 2

Two decades after it went on a worldwide charm offensive, the Toy Story franchise still represents the epitome of the Pixar dream. The first movie from the studio, and the first ever computer-animated feature film, made such an impact it changed the face of animated movies forever and opened the doors for the genre to be taken more seriously – especially at the Oscars. A sequel was both an exciting and worrying concept. But once again the Pixar team pulled it off with exactly the right balance between the groundbreaking animation and damn good storytelling and Toy Story 2 remains a bar against which most animated sequels still struggle to measure up.

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With their human Andy away at camp, the toys are left to their own devices until cowboy Woody (Tom Hanks) is stolen by a toy collector and Buzz Lightyear (Tim Allen) and the rest of the crew set off on a rescue mission in the outside world to save their big-headed buddy. It was the adventure of a lifetime for toys and audiences alike and definitely pushed expectations to infinity and beyond.

American Beauty

Mena Suvari and red rose petals. The motif sprinkled throughout the film and used across marketing campaigns is one of the most memorable movie images of all time. It played no small part in catapulting the actress into the spotlight, alongside her role as choirgirl Heather in American Pie the same year. It was a powerful image in a film that proved a powerful statement from first-time director Sam Mendes, who wowed critics and audiences with his subversive, provocative exposure of the American Dream turned nightmare.

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The film won five Oscars, including Best Picture and Best Director. Conrad L Hall also took home the second of three gongs for his stylish cinematography, and the performances were universally lauded. While his career has been overshadowed by the recent allegations of assault, Kevin Spacey’s unhinged man in the throws of a mid-life crisis earned him his second Academy Award, and Annette Bening was nominated for her role as a wife on the edge trying desperately to cling to the appearance of a happy, normal life (which probably doesn’t involve her daughter watching a video of a dancing plastic bag with their peeping tom neighbour).

The Blair Witch Project

It’s not often a low budget indie film can say it changed a genre, but The Blair Witch Project did just that when directors Daniel Myrick and Eduardo Sánchez took to the woods with nothing more than a handheld camera, three unknown actors and a 35-page outline for a movie. The premise that the movie was created from found footage of a group of student filmmakers who went missing while making a documentary captured the world’s attention.

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Not only was the found-footage aspect a welcome change that would shake up the genre and spawn its own sub-genre of movies, but the movie would also blow traditional marketing techniques wide open. Setting up a website, blairwitch.com, with fake news footage and details about the legend and the filmmakers’ expedition, the campaign purported the events to be real. The actors disappeared from view and their parents even received letters of sympathy about their missing children.

Even for those who weren’t sucked in, the minute the film began, with its claustrophobic feel, extreme close-ups, torches going off at inopportune moments and those teeth, audiences were quickly pulled into the same heightened sense of fear as the actors (whose reactions were mostly real) – listening out for every crack of a twig, eyes peeled for every minute sign of danger. The movie opened up low-budget filmmaking and promotion to those without connections or money. And it scared the bejesus out of us along the way.

American Pie

Thanks to this movie we’ll never look at an apple pie the same way again. The teen comedy franchise has provided more butt-clenchingly awkward moments on screen than any other over the years (20), and the sequels and spin-offs (7). And, gross-out as it is, the reason we still remember the film is because of the characters – they’re actually pretty endearing. Yes, it’s full of stereotypes, but it’s also full of strong relationships. The father-son duo of Jim (Jason Biggs) and his dad (Eugene Levy) can find more comedy in a short exchange than the most ludicrous physical set-up. Their comic timing is spot on and Biggs, in particular, would struggle to find another role that he embodied quite so fully.

Then there’s Alyson Hannigan’s band geek Michelle, whose one-liners have gone down in history, and of course, Stifler’s Mom (Jennifer Coolidge) – who is actually only in one scene, but completely steals the movie. It’s a slice of American high school life that’s still worth tucking into two decades later.

Girl, Interrupted

Winona Ryder executive produced and gave a fantastic performance in the lead role of this biographical drama about a teenager’s stay in a mental hospital in the 1960s, but it was Angelina Jolie who would ultimately turn heads. As unpredictable sociopath Lisa, Jolie’s charismatic performance made Hollywood sit up and take notice, and earned her an Oscar for Best Supporting Actress. She’s the wild heart of a film that remains a thoughtful exploration of female adolescence and the intricacies of mental health, but the movie also has important things to say about bourgeois values and the abuse of authority.

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That Susanna (Ryder) was committed to an institution after a botched suicide attempt and one session with a psychologist she’d never seen before still resonates, as does her willingness to take solace somewhere she didn’t technically belong. But, as her infamous line goes, “Sometimes the only way to stay sane is to go a little crazy.” And, as Stranger Things has reminded us, women on the edge is what Ryder does. And she does it here to near perfection.

The Iron Giant

The first feature-length animated movie from Brad Bird – the man who would go on to bring us The Incredibles and Ratatouille – The Iron Giant seamlessly mixes hand-drawn and computer-generated animation in a turn-of-the-century movie that pays homage to tradition, while ushering in the new. It wasn’t a big hitter at the box office, but it earned almost universal critical praise for its wit, intelligence and subtlety at a time when we didn’t take for granted kids films working at an adult level. It’s not cutesy, wide-eyed animation, but a compelling story with well-drawn characters that often makes you forget you’re not watching live-action.

Impish humor and a fairy tale sense of adventure throw a soft blanket over the political parable, set in small-town America during the late 1950s when Cold War paranoia was at its peak. Familiar themes of fear of the unknown, being an outsider and the potential for destruction within us all add to the E.T.-like story, adapted from poet laureate Ted Hughes, of a young boy who meets a being from outer space, earns its trust, then must hide it from his mother and the authorities. Unlike the Pixar movies that would spawn similar releases over the years, it stands alone as unique and very much of its time.

Being John Malkovich

A puppeteer discovers a door behind a filing cabinet of the 7½th floor of a faceless office building that leads into the mind of John Malkovich. Wait, what? The premise for the first feature-length movie from music video director Spike Jonze was pretty out there to say the least. And it only gets more inventive (and weird) as the story unfolds. An existentialist fantasy of mind-blowing scope, nobody had seen anything like it before. Writer Charlie Kaufman came up with the story and used it as his portal from the world of TV into feature films, while John Cusack became involved as puppeteer Craig after asking his agent for “the craziest, most unproduceable script you can find.”

Cameron Diaz shed her blonde bombshell image and is almost unrecognizable in the role of Lotte, Craig’s wife, who falls for his co-worker Maxine (Catherine Keener) while inside Malkovich’s head. Oh, and of course John Malkovich plays himself and, at one point he enters his own mind through the portal. It’s almost too much for our tiny brains to comprehend, and it blew the minds of critics, audiences and the Academy, with three Oscar nods – for Jonze, Kaufman and Keener.

The Green Mile

After the success of The Shawshank Redemption five years earlier, director Frank Darabont returned with his second feature movie – another Stephen King adaptation set in a prison. It was ambitious, if not purely for the fact it runs over three hours long. While a few commented it was like enduring a life sentence themselves, the overall reception was positive – in no small part due to Michael Clarke Duncan. His powerful performance as John Coffey, a hulking black man imprisoned on Death Row (aka The Green Mile due to its green tiled floor) for the murder of two young girls, earned him an Oscar nod, and rightly so. It’s an incredibly nuanced turn as a man judged by his size and colour, who secretly possesses miraculous gifts.

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Tom Hanks was riding high, having already won two Oscars that decade and nominated for another for Saving Private Ryan the previous year. He was a big enough name to hang any movie on, but his star power wasn’t necessary here. His performance as the guard at the Cold Mountain Penitentiary in the 1930s, who discovers John’s powers (and his humanity), still packs an emotional punch decades on.


Paul Thomas Anderson had established himself as some kind of Hollywood wunderkind when he started work on the most complex and ambitious narrative of his career. He was only 26 when his first movie, Hard Eight, came out and made a splash at Sundance, followed the next year by the Oscar-nominated cult favorite Boogie Nights. What he originally conceived as a small, intimate movie grew bigger and bigger until it emerged as a three-hour epic scattered with jigsaw pieces of story and heavy with symbolism (the frogs confused a lot of people). It followed the interconnected lives of lost souls living in the San Fernando Valley in a sprawling soap opera of success, failure, love and the inability to do so.

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Anderson gathered a cast of some of the greatest actors of the time – Tom Cruise, Julianne Moore, Philip Seymour Hoffman, William H Macy and Jason Robards among them – and coaxed out unforgettable performances, for which Cruise received his last Oscar nomination. Anderson received the second of eight Academy nods for his screenplay, while Aimee Mann, whose music is integral throughout the movie and scores the poignant “Wake Up” moment was also nominated for Best Original Song (for Save Me). It’s an emotional rollercoaster of a movie, and by the time Anderson hits us with the deus ex machina ending, it’s been an exhausting but poignant ride.

Office Space

A true cult classic, this live-action debut from Mike Judge (the man behind Beavis And Butthead) didn’t make much of an impact at the box office but has since picked up a huge following on DVD. It starred Jennifer Aniston at the height of her Friends fame and in the broils of her role as America’s sweetheart opposite Brad Pitt. Had it been better received at the time, it might have been a breakout role for Ron Livingston, still riding the wave of Swingers, as everyman Peter – a computer programmer who hates his job and the cubicle culture that surrounds him.

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The movie offers up an array of quotable lines and a jarringly funny rap soundtrack to accompany the mundane lives of its characters – which are only punctuated by the faux excitement of Hawaiian shirt day, occasional bouts of stapler theft, and the levels of “flair” at the local fast-food restaurant. It was like a darker Dilbert, and it struck a chord. People reportedly quit their jobs and websites were set up where disgruntled office workers could share the angry, offensive and just plain ridiculous memos from their own bosses. It made office workers into a tribe that still stands strong today.

The Talented Mr. Ripley

Told through the eyes of the “bad guy,” as it were, we’re uncomfortably complicit in Anthony Minghella’s slow, seductive thriller about a sociopath who assumes other people’s identities. And, not just that, as we get sucked further into his world, we actively root for him to succeed – such is the impressive nature of his talent and his capacity to bullshit his way out of any situation. In one scene, where Ripley has to keep his landlady, the police, and a friend of the man he’s impersonating at bay at the same time we’re with him every heart-thumping second.

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Minghella was Oscar-nominated for his smart adaptation of Patricia Highsmith’s novel, which was previously adapted as Purple Noon in the 1960s. Both the set and costume design also got nods for the ridiculously stylish visuals, the costumes, in particular, bringing Jude Law’s charming playboy into bronzed, beautifully tailored focus ready for his Oscar close-up. It was a step away from the heartthrob status Matt Damon had enjoyed, particularly since writing and starring in the Oscar-winning movie that would make his career – Good Will Hunting. And strong turns from Philip Seymour Hoffman as Dickie’s boorish friend and Gwyneth Paltrow (fresh out of the phenomenal success of Shakespeare In Love) as his girlfriend complete the sleekly presented package.

Run Lola Run

The buzz surrounding German director Tom Tykwer’s fourth feature film took off from the first festival screening and just kept running. Coming in under an hour and a half, it was short, sharp and slick in a way that left audiences breathless. Frenetically jumping between live-action, animation and still photographs, the blink-and-you’ll-miss-it editing used everything from slow-mo to split screen to create a pulsating, hypnotic, candy-pop daydream – all set to a pumping techno soundtrack that kept hearts racing as fast as its captivating protagonist.

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Franka Potente, as the titular flame-haired punk, spends almost the entire movie running, as she plays out three Sliding Doors-style scenarios of her pounding the streets of Berlin to find 100,000 marks before her boyfriend falls into the hands of gangsters. She has 20 minutes to come up with the money – it’s literally a race against time, every tiny decision setting in motion a chain reaction that could lead to success or death. Potente would go on to cement her international reputation in the similarly fast-paced Bourne movies, but would struggle to find a role with quite the same energy and impact as this stylish burst.


It may sound like just another high school comedy, but Alexander Payne’s biting satire is a dark, funny and cleverly written exploration of human behavior. Using a high school as a microcosm for the American social and political landscape it tells the story of an election for student president. Tracy Flick is the terrifyingly perky go-getter running unopposed and driving teacher Jim McAllister up the wall. The iconic character is deeply rooted in our vision of the high school experience and Reese Witherspoon teeters on the edge of control in one of her most memorable roles, imbuing her determined Little Miss Perfect with a desperation that makes us feel for her, even as we root for her to fail.

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Matthew Broderick is an ample cushion for absorbing one comedic blow after another as he devotes his life to taking down a teenage girl. He hates her, he lusts after her against his will, and ultimately he becomes obsessed with breaking her. He even drafts in popular but dim-witted jock Paul (Chris Klein, who also appeared as Oz in American Pie the same year) to run against Flick, which causes his sister Tammy (Jessica Campbell) to jump in as an anti-establishment force determined to take down the student government (lest she have to “sit through one of these stupid elections again”). In Payne’s hands, nobody comes out unscathed in what is a sharp melting pot of sex, politics, ambition, corruption and obsession.

Boys Don’t Cry

Hilary Swank won an Oscar for her thoughtful and nuanced portrayal of transgender teen Brandon Teena in this landmark movie based on real events. Brandon leaves his hometown after his ex-girlfriend’s brother discovers he was born female, and creates a new life in a small Nebraskan town. But although he fits in with the guys and proves a hit with the girls – particularly girlfriend Lana (Chloë Sevigny) – history soon repeats itself, with violent and tragic results.

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Sevigny was also nominated for Best Supporting Actress, and her Lana is a glimmer of hope in humanity in a film where the rest of society doesn’t come off particularly well. She’s strong in the face of daily objectification and belittlement and loyal in a way that puts most of us to shame. The film was one of the early representations of the transgender experience in Hollywood, and an important one, even while it contributes to the argument about the repeated casting of cis-gendered actors in transgender roles.

Three Kings

A major studio release with a daring, indie weirdness, David O. Russell’s action-adventure remains one of the best films about the Gulf War to date. What begins as a potential heist unfolds into a damning satire of America’s Operation Desert Storm. The story itself is bizarre – in the aftermath of the war, four soldiers band together to steal millions of dollars worth of gold…from Saddam Hussein. Seems doable. And smart. But, actually, one of the things that sets this movie apart is its intelligence. Characters are of a type, sure – it’s still a war film – but they’re more fully rounded than most. Even the husband of a woman killed by Hussein’s men is spared a simple “Iraqi” identity and presented as an educated man still pissed that the Americans bombed his cafes.

The visuals also add to the off-kilter feel, with exploding cows and the iconic slow-mo shot of a bullet travelling through the body – a grotesque moment of body horror bandaged with humor. It’s the film that marked O. Russell’s arrival and also helped George Clooney cement his move from small screen to big a little more firmly (he had One Fine Day and Batman & Robin to make up for, after all). There was a lot riding on it for both men, and reportedly things got a touch heated between the two during filming, but the result was a war movie that blew the genre, and both careers, wide open.

Eyes Wide Shut

What was to be Stanley Kubrick’s final movie is a surreal, uncomfortable, but seductive film that plays out like an erotic fever dream. Everything is highly stylized, from the ballroom lit up like the Overlook Hotel to the bizarre costumes of the ritual-like orgy and the long, unbroken tracking shots that have become a calling card for the director. Tom Cruise and Nicole Kidman star as a couple married for nine years (which they were in real life at the time of the film’s release) who reach breaking point when Kidman’s Alice admits an intense sexual fantasy about another man.

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Though Cruise chews up most of the screen time, Kidman is incredible with a smart, subtle performance that says much more with one look than an entire scene of dialogue. It’s a story of intimacy and loneliness, of sexual deviancy and morality, desire and violence –ultimately of sex and death. As William Harford, Cruise’s labyrinthine journey into a sexual underworld is vivid yet typically enigmatic, scored throughout by Jocelyn Pook’s compositions, which veer from simple piano tinkles to full orchestral swells – as much a central part of the atmosphere as the lush visuals. Such is the heaviness of its erotic aura, repeat viewings reveal there’s actually a lot less sex in the film than you remember.