“I don’t know the future,” shrugged Neo in 1999’s The Matrix. “I came here to tell you how it’s going to begin.” With him, on-screen and off, as The Matrix plunged audiences into the future of cinema, which 20 years later, looks like the Wachowskis’ wildest dreams: 1s and 0s everywhere and Keanu Reeves still kicking ass.

The Matrix. Magnolia. Being John Malkovich. Fight Club. The Blair Witch Project. The Sixth Sense. Office Space. Man on the Moon. The Talented Mr. Ripley. Boys Don’t Cry. Three Kings. Toy Story 2. The Iron Giant. Eyes Wide Shut. Cruel Intentions. Election. American Pie. Notting Hill and Runaway Bride. 1999 might be the greatest year of modern cinema. I think so. If you aren’t nutty about two-thirds of these films, do you even like movies?

What’s certain, however, is that 1999 is the most pivotal year of modern cinema – the moment that Hollywood anointed the chosen ones who would become the heroes of the new millennium, from David Fincher to Spike Jonze to an ingenue named Angelina Jolie, who introduced herself to the public by winning best supporting actress for playing a sociopathic mental patient. Girl, Interrupted wasn’t Jolie’s first film. But it was the movie that engraved her on the A-list, a pattern that’s also true for Hillary Swank in Boys Don’t Cry, Jude Law in The Talented Mr. Ripley, Reese Witherspoon in Election, Heath Ledger in 10 Things I Hate About You, and Russell Crowe in The Insider.

What explains 1999’s extraordinary films? DVD sales began in 1997 and flooded studios with extra cash, especially in those first years as home viewers built their collection. Studios invested the windfall in a generation of upstart directors, predicting that audiences would buy a good film twice: once in the theater, and again for their shelf.

Ice Cube, Mark Wahlberg and George Clooney in Three Kings. Photograph: Allstar/Warner Bros

Suddenly, the geniuses who’d been discovered during Sundance’s 90s indie wave were entrusted with millions in play-cash plus marketing muscle. It was a creative renaissance. Directors seized the chance to get weird. Paul Thomas Anderson scored $37m to assemble the lyrical montage Magnolia. David O Russell shouldered $47m to satirize the Gulf war. Even Spike Jonze, a music video director with zero film credits to his name, secured $13m to transport audiences to a multiverse of John Malkoviches.

The risk paid off. These up-and-coming directors became major 21st-century voices. Still, part of the reason Anderson, Russell and Jonze are still the kings of the kooks is that today’s directors haven’t been given the same golden ticket. The talent exists; the cash doesn’t. Ambitious mid-priced films went extinct when the DVD empire began to crumble in 2008. Instead of betting on auteurs, studios put their chips on big screen superheroes. Break out at this year’s Sundance, and instead of being handed the freedom to dream, you’ll be given the keys to a franchise – and a conference table of producers as chaperones. Or you’ll stay small and scrappy forever, cranking out a terrific body of work that struggles to be seen amid the crush of streaming media competing for the audience’s attention at a couple bucks a pop, or flat-out free.

Much has changed. Twenty years ago, two big-budget Julia Roberts romantic comedies atop the box office chart was a given. Now, both the genre and the star have been squired to streaming. Raunchy teenage comedies like American Pie are, like, totally awkward in an era where dating and sex are on the decline, and raunchy teenage dramas like Cruel Intentions are cloistered on TV to be recast as Riverdale characters who audiences can still safely see as cartoons.

Haley Joel Osment in The Sixth Sense. Photograph: Allstar/Buena Vista

Sex is out, horror is in. And for that, we can thank 1999, too, as The Blair Witch Project launched a mania for mirco-budget nightmares that refuses to crawl back under the bed. The Blair Witch Project (which still holds up fabulously) begat Paranormal Activity which begat Blumhouse Pictures who begat everything from The Purge to Get Out to Insidious to Sinister. Add all four of their budgets together, and they still cost less than Being John Malkovich – even without inflation. As for M Night Shyamalan, hyped as “The Next Spielberg” on the cover of Newsweek after The Sixth Sense, he’s finally accepted the Spielberg’s populist template never fit an egotist who prefers to provoke. He’s also found happiness in low-budget thrills like The Visit, Split and the upcoming Glass (all three produced, of course, by Blumhouse).

Probe the films of 1999 and a suspicion slithers in that we’re stuck in The Matrix ourselves. The near past is repeating like a programming glitch, or, say, an endless parade of Malcovi. There’s deja vu remakes of Tarzan and The Mummy and Pokémon and Galaxy Quest and the just-announced Toy Story 4. The Star Wars universe continues to propel the box office, as it’s done since The Phantom Menace. Michelle Williams and Kirsten Dunst’s comedy Dick about two teen girls who bring down Nixon’s corrupt administration makes for an apropos rewatch, as does Alexander Payne’s black comedy Election, in which a high-achieving blonde female candidate hamstrung by sexism and fraud loses her campaign to a dummy who never seriously intended to win. And if the Oscars mimic this year’s Golden Globes, Green Book winning best picture will be cringeworthy as American Beauty beating a field of worthier contenders in 1999. At least Kevin Spacey won’t be in attendance.

But we’re also feeling a deeper connection to 1999, one that vibrates in our wiring. The Y2K panic triggered film-makers to think pessimistically about the future of human survival. The Wachowskis assumed we were toast. Kevin Smith’s Dogma and the Arnold Schwarzenegger action flick End of Days embraced the apocalypse. And David Fincher’s Fight Club and Sam Mendes’s American Beauty feared that mankind had become too weak and materialistic to survive the millennium.

What’s scary about today – a time in which our nerves are again quivering with anxieties about capitalism, despotism and an all-but-inevitable environmental catastrophe – is that we’ve now been shaped by those films’ misanthropy. Not just the mens rights activists who’ve adopted The Matrix’s red pill/blue pill analogy as their own twisted “truth” or the Twitter trolls incubated on the internet who idolize Fight Club’s Tyler Durden. As for the solution, Fincher suggested boxing and domestic terrorism. Mendes touted weightlifting, crushing on underage girls, and, ultimately, suicide.

In 1999, our heroes didn’t win. They failed, they disappeared, they died, they blew up their world. And they left a residue of cynicism we’re still scraping off, from our political apathy to the studios’ resentment that their DVD cash cow dropped dead. “The future is our world, Morpheus,” gloated The Matrix’s Agent Smith. He was right. Yet, we can change our tomorrow.