By Noah Gittell

The great years in film history usually happen due to a specific confluence of factors, including a breakthrough in technological innovation, a cultural inflection point, and an historically talented generation of filmmakers or actors coming of age at the right time. The year 1939, often cited as the best year in film, had “The Wizard of Oz,” which showcased a groundbreaking use of color and a star-making turn from Judy Garland at a time when Americans were ready for a new escapism after a decade of economic hardship. Also in 1939, “Gone with the Wind,” Stagecoach,” “Mr. Smith Goes to Washington,” “Ninotchka,” and “The Women” reflected the same changes.

Then 25 years ago, it happened again. In 1999, rapid advancements in computer-generated imagery created new creative opportunities for filmmakers, while an uber-talented group of young directors who benefited from the independent film boom had just graduated to working with bigger budgets and movie stars. Throw in the anxieties over Y2K and the coming of the new millennium, and you had a rare breeding ground for artistic greatness.

Although maybe not the best films of this year, the two that most typify it are “The Matrix” and “The Blair Witch Project.” Each represents the possibilities of the internet era, albeit in vastly different ways. “The Matrix” created an entire allegory for life online, with its hero John Anderson/Neo toggling between the real world and one where he could be cooler, stronger, and more important, just by wishing it so. The found-footage, micro-budget “Blair Witch Project” could have been made in any era — it was filmed in the woods with just three actors — but its incredible marketing hook left viewers wondering whether the events of the film were real or fictional. This was buttressed by a much-viewed website that played up the film’s faux-reality, further muddying the water and adding to the intrigue, while early internet adopters spent hours investigating and debating in internet chat rooms.

Neither of these films made much of an impact at the Oscars that year, which is further evidence that the Academy isn’t great at identifying those films that will stand the test of time. “American Beauty,” which swept the Oscars, has lost some of its prestige over the years, due to our growing distaste for narratives about middle-aged men lusting after minors. The accusations of sexual assault made against Best Actor winner Kevin Spacey (he was acquitted) surely haven’t helped. In its place, a great number of early films from now-established filmmakers have assumed its spot in the canon of 1999.

David Fincher earned a following with “Seven” and “The Game,” but “Fight Club” demonstrated his ability to capture the zeitgeist without sacrificing his artistic voice. The film, which both glorifies and satirizes anarcho-fascism, continues to stir controversy today; it is often cited as inspiration on internet message boards by incels and alt-right activists. The film’s narrator — a white-collar worker who forms a new underground society — has much in common with Neo in “The Matrix,” and both films presaged a growing dissatisfaction with America’s traditions and institutions.

Paul Thomas Anderson followed “Boogie Nights” with “Magnolia,” an operatic mosaic of love lost and found in southern California. It didn’t make a profit upon its release, but the film is still revered by his fans for its bold narrative strokes and power-ful emotions. With “The Sixth Sense,” M. Night Shyamalan became synonymous with the twist ending, a popular trend in the late ’90s that reflected a rejection of cinematic convention. The same could be said of “Being John Malkovich,” the radical film from Spike Jonze that foretold how the internet — a place where we could literally become other people — would merge with our celebrity obses-sion to frightening impact.

The list goes on: “Three Kings,” “The Talented Mr. Ripley,” “Election,” “Office Space,” “Eyes Wide Shut,” and “South Park: Bigger, Longer, and Uncut,” not to mention international standouts such as “All About My Mother” and “Audition.” Others, like “The Iron Giant,” “Drop Dead Gorgeous,” and “10 Things I Hate About You” found their devotees later, either through extended runs on basic cable or old-fashioned word of mouth. 

These films have more in common than their artistic excellence. They represent a snapshot of a moment in time, when the disillusionment of a generation met the possibilities of the medium. It might never come again.