By Darren Franich
Updated October 10, 2014 at 06:08 PM EDT

It’s been 15 years since 1999, because that’s how time works. 1999 is generally considered a great year for movies. Transformative, even: A diverse array of films, directed by a fleet of up-and-coming filmmakers, all arriving at the multiplex back when cable was lame enough and the internet was slow enough to make the multiplex a place that mattered.

If you happened to be young in 1999—or young-ish—it was possible to feel like you were seeing the entire cinematic art form evolve in front of you. Fifteen years ago this month was Three Kings and Fight Club and Being John Malkovich, instant-cult films helmed by young/hip directors (all of whom successfully grew into middle-aged/important directors.) They followed The Matrix and Election and The Sixth Sense and The Blair Witch Project; still to come was Dogma and Magnolia. By late November, Entertainment Weekly declared 1999 “The Year That Changed Movies.”

Movies are like wine: They age well, except when they don’t. Wild assertion: If you were to take a straw poll of the American subconsciousness, I’d be willing to bet that the 1999 movie with the most consistent uber-positive rating would be Office Space. The reasons for this are legion, but two stick out in particular. Office Space is one of the best movies ever made about hating your job, and one of the best movies ever made about being bored–two across-the-board human experiences that movies are (historically, respectively) just-okay and utterly terrible at dramatizing. And Office Space was uniquely designed to age well. Sure, the computers look old and the clothes are too big. But that’s in service to the film’s banal drudgery: The character’s lives look more accurately lame every year.

If you were take a slightly more highbrow straw poll–more wild assertions now–I’d bet that, of all the movies of 1999, our current across-the-board nobody-hates-it-and-most-people-love-it Best pick would be The Talented Mr. Ripley. The reasons for this are sad, obvious, prosaic, and weirdly inspiring. Sad: The recent passing of Philip Seymour Hoffman. Obvious: Every single up-and-coming actor in the film’s main cast turned into one of the greatest and/or most overexposed actors of the ensuing decade. Prosaic: The movie is available on Netflix streaming, which is more than half the battle for a film’s cultural longevity now that nobody knows how to rent DVDs and most people are too cheap to pay for a single movie and too lazy to figure out how to watch movies illegally.

But, Weirdly Inspiring: The Talented Mr. Ripley felt a bit old-fashioned in 1999, when it was a period-piece throwback thriller that didn’t have a chrono-blasting narrative and didn’t feature bullet-time digital effects and didn’t end with the revelation that one of the characters was actually a digital schizophrenic delusion ghost. 15 years later, that “old-fashioned” vibe just looks like genuine classicism: More refined filmmaking, reflective of whatever you think is lacking in movies today, good acting or sharp twists or unhappy endings or the notion of filming a major movie somewhere besides a greenscreen in Detroit.

Other movies from 1999 have aged well–maybe better than they deserve. The pre-millennial bumper crop of teen movies has led to a bumper crop in teen-movie nostalgia for She’s All That, Varsity Blues, Cruel Intentions, and American Pie–a nostalgia that is barely justified by the fact that everyone seems to generally agree that 10 Things I Hate About You was the best of the bunch. Nobody really remembers most of Any Given Sunday, but Al Pacino’s “Game of Inches” soliloquy is one of the great pump-up speeches, with a running time that’s just right for YouTube. (It might be the last great cheesy-transcendent moment in Hollywood sports movies, insofar as Hollywood basically stopped making sports movies.)

There’s a certain intersection of comedy freak and repressed nerd who will always stump for Galaxy Quest. Anytime Reese Witherspoon makes a movie that’s even barely good, someone will always bring her absurdly brilliant performance in Election. Anytime Samuel L. Jackson gives an inspiring speech in a movie, Deep Blue Sea gets approximately half-a-percent better. If you like romantic comedies–which is to say, if you miss when they made romantic comedies–then Julia Roberts’ summer of 1999 could be the golden age: Notting Hill in May; Runaway Bride in August. And there are men of a certain age who can vividly recall that there was a movie called Entrapment, but they can’t remember the plot, the characters, the dialogue, or indeed anything at all besides two seconds from the trailer:

On the flip side: Some of the most important movies from 1999 have aged strange. Some have suffered minor backlash; some of them were so completely appropriated by the mainstream, their bold-new-newness becoming retroactively cliché; some were maybe never good to begin with. But what movie from 1999 has aged the worst? Some possibilities, with explanation:

The Matrix: There was a period when everyone agreed that The Matrix was going to be the action-fantasy saga of whatever generation we were, the Star Wars of the new millennium. This was before The Matrix Reloaded, a totally decent action movie ruined by a goofy dance number and the decision to climax with an old bearded man babbling towards the camera, and The Matrix Revolutions, the first magnificently disappointing finale in a decade filled with magnificently disappointing finales. Over a decade later, most people have quietly agreed to ignore the sequels, but the original Matrix is more of a solid action movie than a cultural obsession. Consider this: Fifteen years later, everyone seems weirdly okay with the fact that the Star Wars of the new millennium might just be Star Wars.

The Blair Witch Project: The backlash started early on Blair Witch, the movie that invented the found-footage horror genre and simultaneously invented people complaining they were totally over the found-footage horror genre. You can’t say this without sounding like an old person, but: Back in 1999, when people still believed in truth, a not-inconsiderable amount of moviegoers were disappointed to learn that Blair Witch was a fictional movie. Or anyhow, that was one of the narratives the media concocted to explain the wave of people disappointed by The Blair Witch Project. (Also possible: Lots of moviegoers were not necessarily prepared to watch a movie about people waving cameras at trees.) The fact that everyone could make a better-looking movie than Blair Witch on their smartphone arguably makes Blair Witch more fascinating as an artifact. But it sits weirdly in film history: Too popular to be a cult film, too low-key to be rewatchable. Also not helping matters: The flat-out awful follow-up Book of Shadows. From a cultural-history perspective, the best thing about The Blair Witch Project is probably that it isn’t Cloverfield.

The Sixth Sense: Some twists don’t age well. Some twists become everyone’s go-to example for what, precisely, a great twist is. But the gradual 2000s descent of M. Night Shyamalan makes any praise for The Sixth Sense feel depressingly elegiac.

American Beauty: Suburban ennui, the struggle of the middle-class straight white male, the moony-eyed teenager who films plastic bags because like beauty man, Thora Birch: American Beauty is like a veritable laundry list of Things That Seemed Important Until They Suddenly Didn’t. The reboot of Kevin Spacey as a lovable ham has probably raised American Beauty‘s stature, but this is one of those popular-at-the-time Best Picture winners that almost no one will admit to ever liking.

Star Wars: Episode One–The Phantom Menace: Possibly aging better than you think, given that a generation of kids has grown up on the candy-colored digital effects pioneered by George Lucas and ILM in the prequels. Over a decade of geek loathing has also created a natural counter-backlash–the “It’s Not So Bad!” argument. Also helping matters: The Abrams-fronted sequel looks to be an aesthetic recreation of the original trilogy, all bright-orange pilot suits and janky-grit Millennium Falcons, which makes the rat-tails-and-priest-robes blandness of Phantom Menace look like a genuine aesthetic decision. It’s still terrible, but your niece or nephew born in a year that starts with a “2” might disagree.

Dogma: Whichever cult of Kevin Smith you belong to, Dogma is probably not one of the important movies. Clerks is the defining classic; Mallrats is the fun one that people either like or despise; Chasing Amy is the “quality” picture and the best supporting evidence for anyone who wants to pretend they always thought Affleck was a good actor. (In my humble opinion, Dogma is the best thing Smith’s ever done. Also in my opinion, the Dogma DVD commentary is the best thing Affleck’s ever done.)

South Park: Bigger, Longer, and Uncut: Feels like it’s receded from the public consciousness, but only because South Park spent the next decade-plus being consistently good and frequently brilliant in an in-your-face topical way.

Go: Currently forgotten, but feels like it will become more important if/when ’90s nostalgia veers towards the latter, rave-ier part of the decade.

The Green Mile: Currently forgotten, thank God.

Fight Club: There was a time when I thought Fight Club was one of the coolest movies ever made, and the film’s influence could be felt throughout the next decade. Big-budget movies copped Fight Club‘s gritty-glam style; in May, Men’s Journal claimed that Brad Pitt-as-Tyler Durden basically invented the modern action-hero body. But whole stretches of the movie sit weird now–it’s another vintage white-dude-problems movie, a less-funny Office Space mixed with a quarterlife American Beauty, complete with an incoherent ending that looks awesome and feels meaningless. Put it this way: How fondly you remember Fight Club now probably depends on how many times over the last 15 years you heard a rich bro explain how Fight Club totally nailed it, man, ATMs are evil.

What movies from 1999 have aged poorly? Which have aged well? Email me at, and we’ll chat further in Monday’s edition of the Entertainment Geekly mailbag.