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1999 was an extraordinary year for movies. 20 years later, here’s what it can teach us.

From Fight Club and American Beauty to Toy Story 2 and The Talented Mr. Ripley, 1999’s bumper crop has lessons for 2019.

Eyes Wide Shut, Fight Club, Tarzan, and Election were just four of the great films that came out in 1999.
Eyes Wide Shut, Fight Club, Tarzan, and Election were just four of the great films that came out in 1999.
Warner Bros.; 20th Century Fox; Disney; Paramount
Alissa Wilkinson covers film and culture for Vox. Alissa is a member of the New York Film Critics Circle and the National Society of Film Critics.

Riddle me this: What do all of these movies have in common?

Fight Club. Office Space. Eyes Wide Shut. Cruel Intentions. The Matrix. Notting Hill. Star Wars: Episode 1 — The Phantom Menace. Election. American Beauty. Never Been Kissed. The Blair Witch Project. Run Lola Run. South Park: Bigger, Longer, and Uncut. The Insider. Boys Don’t Cry. Runaway Bride. Austin Powers: The Spy That Shagged Me. Dogma. Toy Story 2. The Green Mile. Deuce Bigalow: Male Gigolo. The Limey. Three Kings. The Thomas Crown Affair. Big Daddy. 10 Things I Hate About You. Any Given Sunday. Magnolia. The Talented Mr. Ripley.

Cult favorites, rom-com classics, teen movie standards, trendsetting horror, wildly successful sci-fi, transgressive melodrama, and the most anticipated (and possibly the most reviled) space opera prequel of all time.

Believe it or not, they all came out in 1999.

Every year has good films, but a combination of factors — studio appetite for risks, the rise of some daring young directors, and the happy serendipity of a lot of people just making a good movie that year — led to one point: a year that was uncommonly good for movies.

The Blair Witch Project changed the movie marketing game in 1999.
The Blair Witch Project changed the movie marketing game in 1999.
Artisan Entertainment

There’s no one reason this happened, nor one conclusion to draw. 1999 was a very different time than 2019.

But a look back at the year’s movies points illustrates how different the movie landscape is 20 years later — and helps not just show a few factors that made 1999 the extraordinary movie year it was, but hint at some good new year’s moviegoing resolutions for audiences too.

The top-grossing movies two decades ago weren’t all reboots and sequels

Take a look at the top 10 grossing films in North America in 1999:

  1. Star Wars: Episode I — The Phantom Menace
  2. The Sixth Sense
  3. Toy Story 2
  4. Austin Powers: The Spy Who Shagged Me
  5. The Matrix
  6. Tarzan
  7. Big Daddy
  8. The Mummy
  9. Runaway Bride
  10. The Blair Witch Project

Now, for contrast, look at the top 10 grossing films in North America last year:

  1. Black Panther
  2. Avengers: Infinity War
  3. Incredibles 2
  4. Jurassic World: Fallen Kingdom
  5. Deadpool 2
  6. Dr. Seuss’s The Grinch
  7. Mission: Impossible — Fallout
  8. Ant-Man and the Wasp
  9. Solo: A Star Wars Story
  10. Venom

There are some notable similarities between the two lists. Both contain a follow-up to a beloved Pixar film (Toy Story and The Incredibles). Both contain a Star Wars movie too. Both contain entries in long-running franchises. And both contain animated movies — Tarzan and The Grinch — that remade old stories into new ones.

American Beauty eventually won Best Picture.
American Beauty eventually won Best Picture. Which, when you think about it, is pretty wild.

But you’ll notice at least one big difference between the two: Not one film on 2018’s list is based on an original idea, which is to say that every single one is a reboot, a sequel, or a story based on a beloved commercial property with an already established audience, such as Venom or Black Panther. Half are centered on comic book characters.

By contrast, fully half of the top-earning movies of 1999 — The Sixth Sense, The Matrix, Big Daddy, Runaway Bride, and The Blair Witch Project — are original stories. One more, The Mummy, is at best a very loose remake of a 1932 film, and not one that many audiences in 1999 would necessarily have remembered.

And even the sequels on the list are unusual. The Phantom Menace, whatever its faults, isn’t a sequel; it’s a prequel, one that adds many new characters and storylines to the Star Wars universe. Toy Story 2 is one of the best sequels ever made. Tarzan is a remake, in the way that most Disney animated films have been remakes of something, but a remarkably successful and original one. And The Spy Who Shagged Me is the second in a series of satirical films that skewer another franchise: the Bond movies.

1999 was a year of risk-taking, for audiences and for Hollywood

Outside of the box office successes, many of 1999’s other notable films, whether critically or commercially, were also based on original stories (sometimes incredibly original stories) or went way out on a limb with the stories they adapted. Think of a mind-bending film like Being John Malkovich, or a multi-strand story like Magnolia. Or The Blair Witch Project, which blew apart the world of horror with a highly original marketing campaign and a standard-setting found-footage conceit.

Meanwhile, movies like Cruel Intentions and 10 Things I Hate About You served up new spins on very old stories (Les Liaisons Dangereuse and The Taming of the Shrew, respectively). Others, like Office Space and Galaxy Quest, effectively satirized very familiar parts of American life (in this case, life in a mundane corporate job and science fiction fans’ obsession with the genre).

10 Things I Hate About You is based on Shakespeare’s The Taming of the Shrew.
10 Things I Hate About You is based on Shakespeare’s The Taming of the Shrew.
Touchstone Pictures

It was even an exceptionally good year for movies that felt original, even though they were based on books. Fight Club (based on a 1996 Chuck Palahniuk novel), Election (based on a 1998 Tom Perrotta novel), The Talented Mr. Ripley (based on a 1955 Patricia Highsmith novel), Mansfield Park (based on an 1814 Jane Austen novel), and Girl, Interrupted (based on Susanna Kaysen’s 1993 memoir) are all adaptations that have stood the test of time. These films succeeded partly because they weren’t slavishly faithful to their source material. Instead, they messed with or even reimagined their source material in order to make a good movie.

In 1999, untested talent made waves

Some of 1999’s biggest films came from young, relatively untested talent. The Matrix was the Wachowskis’ breakout film. The Sixth Sense made M. Night Shyamalan a household name. Brad Bird, who would go on to become one of Pixar’s most important talents, made his directorial debut with The Iron Giant. And the low-budget Blair Witch Project, from 30-something newcomers Daniel Myrick and Eduardo Sánchez, took the world by storm and forever altered the horror genre.

And outside of the box office toppers, some of the year’s most critically acclaimed films came from a crop of directors who came out of the indie scene. Mostly male and still early in their careers, many of them had cut their teeth making music videos for the MTV generation. Paul Thomas Anderson was 29 when Magnolia came out. Spike Jonze turned 30 a week before Being John Malkovich was released. Sam Mendes attended the premiere of American Beauty — which would go on to win Best Picture at the Oscars — a month after he turned 34. David Fincher was 37 when Fight Club debuted. And Alexander Payne was 38 when Election was released.

In 1999, The Talented Mr. Ripley boasted an extraordinary cast of young stars who all went on to become A-list talent.
In 1999, The Talented Mr. Ripley boasted an extraordinary cast of young stars who all went on to become A-list talent.
Paramount Pictures

Perhaps most notably, none of the above films were based on properties owned by a major movie studio or media company. These directors were granted the freedom to take on projects of their own.

In 1999, the movie business still had space for movies that took risks and cleared their own paths; studios were willing to greenlight interesting projects even without a guaranteed audience that had already proven their appetite for a given story or property or franchise. Twenty years later, it often seems like the people who control the money in Hollywood are almost exclusively interested in the “sure thing,” the movie with the built-in audience, whether because it’s based on a hit comic book property or a popular novel, or because it’s the third remake of a film with two massive stars in the lead, or because it’s a sequel to a hugely popular film from the past.

In the intervening years, reboots, sequels, and, most of all, comics have drastically changed the North American box office landscape. And even though movie attendance was on the rise in 2018, studios’ reticence to take a chance on new ideas means that burgeoning young filmmakers who got their start in innovative indie films — like Taika Waititi, Ryan Coogler, and Rian Johnson — often get their big-budget breakthrough via some Disney-owned property (Thor, Black Panther, and Star Wars, respectively) rather than with an innovative idea of their own.

1999 was a great year for some genres that have only recently started to show renewed signs of life

In 1999, a few genres were big hits at the box office. But soon after, they virtually disappeared and have only recently started showing up again.

Romantic comedies, for instance, were still big business, and a rom-com could still get major stars to headline. Julia Roberts had two rom-coms come out that year: Notting Hill, in which she stars alongside Hugh Grant, and Runaway Bride, in which she reunites with her Pretty Woman co-star Richard Gere. Never Been Kissed, a rom-com classic, starred Drew Barrymore, fresh off the double success of Ever After and The Wedding Singer. And Malcolm D. Lee’s The Best Man, executive-produced by Spike Lee, raked in far more money than expected, with a star-studded cast led by Taye Diggs and Nia Long.

The Best Man busted box office expectations in 1999.
The Best Man busted box office expectations in 1999.
Universal Pictures

In an adjacent genre, a huge number of teen movies came out that year: Varsity Blues, She’s All That, Cruel Intentions, 10 Things I Hate About You, Election, American Pie, and Drive Me Crazy (with a title changed to match one of the songs from its soundtrack, borrowed from the first album by a fresh-faced Britney Spears). Most of these teen movies feature recognizable young faces of the era (Reese Witherspoon, Sarah Michelle Gellar, Freddie Prinze Jr., Julia Stiles, Heath Ledger, Melissa Joan Hart, James Van Der Beek) and seem obviously calculated to capture the same audience that flocked to shows like Buffy the Vampire Slayer (which starred Gellar and premiered in 1997) and Dawson’s Creek (which starred Van Der Beek and premiered in 1998). It’s no coincidence that the WB TV network — which specialized in shows aimed at teens — launched just four years earlier, in 1995.

But what may be most notable, two decades later, is that while the teen movies that came out in 1999 have proven their staying power — their storylines and production values can feel dated and even problematic today, but they’re still easy to find rerunning on cable and remain audience favorites — not one of them is based on a YA novel or set in a dystopian future. They range from the semi-realistic to the raunchy to the absurd, but they’re all set in a recognizable world (usually an affluent high school), and they’re all attuned to the antics of teens, in the lineage of movies by John Hughes (The Breakfast Club, Pretty in Pink) and Amy Heckerling (Fast Times at Ridgemont High, Clueless). And, once again, while each of them draws on tropes, they’re almost all based on original stories and characters.

Until recently, films like these had seemed to die off, revived only in the past year or two by the flexibility and risk that a company like Netflix, with its deep pockets and relatively low overhead, is willing to take on mid-budget movies. Netflix originals like Set It Up (in which Diggs co-stars) and To All the Boys I’ve Loved Before — not to mention traditional theatrical releases, including indie hits like Eighth Grade and studio fare like Crazy Rich Asians — suggest a revival may be on the way.

Julia Roberts and Hugh Grant captured hearts in Notting Hill.
Julia Roberts and Hugh Grant captured hearts in Notting Hill.
Universal Pictures

The bumper crop of 1999 suggests some resolutions for moviegoers in 2019

There’s no one reason that 1999 produced so many enduring films. Tastes change. Tastemakers change. Studio executives evolve their ideas based on market pressures and audience response. The generation of revolutionary filmmakers who hit their stride in the 1960s and ’70s, like Stanley Kubrick and Martin Scorsese, made lauded films of their own in 1999 (Eyes Wide Shut for Kubrick, Bringing Out the Dead for Scorsese), alongside the 30-something upstarts. Boosted by the experimentation happening in the indie film world, studios wanted to make more daring fare. And in the pre-9/11, pre-recession world, money flowed freely.

Still, there may be some lessons from 1999 that can guide us in 2019 — especially those of us who love movies.

First, it’s important to take chances on movies that aren’t tied to any preexisting property. Yes, it’s expensive to go to the movies, and taking a risk can be, well, risky — especially in a largely post-MoviePass world.

Brad Pitt and Ed Norton tore up the screen in cult favorite Fight Club.
Brad Pitt and Ed Norton tore up the screen in the cult favorite Fight Club.
20th Century Fox

But executives pay attention to box office numbers, and if a movie does well, you can be sure that studios will try to replicate its success however they can. Making decisions about riskier fare may just mean paying attention to critics with taste that’s compatible to your own, or reading reviews out of film festivals. But devoting an evening to a weird-sounding film can result in a memorable moviegoing experience. And because money talks in Hollywood, it may be the key to finding variety at the multiplex of the future.

Second, those who tend to flock to whatever we consider “highbrow” fare — and I include myself in this group — would do well to pay attention to more “middlebrow” genres we might have been tempted to write off in the past. Sure, teen movies seemed to drop off into unfunny raunch-com territory for a minute there. And rom-coms seemed dead for a long stretch. But there’s plenty of life in these genres yet.

And filmmakers who are interested in reinventing beloved genres for today may have some tricks up their sleeves worth trying out. If 1999’s lineup of teen comedies shows us anything, it’s that it is possible not only to freshen up old stories but to come up with new ones — and the most beloved movies of the year show that audiences are plenty capable of flocking to a fresh idea.

A good film can come from anywhere. And if we want movie executives to take the kinds of risks they used to take, we’ll need to take them too.

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