Readers Told Us Their Favorite 1999 Movies. Here’s What Came Out on Top.

Many readers sent us lists, unable to choose just one film, while others gave an elaborate and detailed retelling of a first viewing. Here’s a sampling of what our readers picked, covering everything from teenage escapades to heart-racing thrills to gut-wrenching dramas.

Mike Ruddell of New York:

By 2024, “The Matrix” is feeling more relevant (and plausible!) by the day, thanks in part to our obsession/tension with breeding ever more capable A.I., our cultural fixation on antihero hackers and leakers, our ongoing destruction of the planet, and our weirdly brat green digital culture. At this point only the phones feel dated.

But that’s not what makes this a good movie. “The Matrix” is the best movie of 1999 because of the insanely inventive plot (or conceit?), the thesis-worthy philosophical themes, the kick-ass mishmash of Wing Chun, jujitsu, cyberpunk, shoot-em-up action, and C.G.I. “bullet time” (a term coined thanks to the film), the most “1999” film anyone could possibly think up. As Gen Z would say, “The Matrix” is a vibe.

I still get an adrenaline rush from the closing scene when Neo, fresh off his obliteration of the Agents, puts on his shades, looks to the sky, and FLIES.

Neeraj Gupta of London:

Growing up in India, on a diet of Bollywood movies, “The Matrix” was the first English film that I had watched in a cinema. I distinctly remember being wowed by the plot and coming home to think if all of us are actually living in the Matrix. To this day, I can’t shake that feeling!

It is a cult classic with scenes and props etched in my memory, from the long black leather coats to Morpheus’s frame less glasses, and of course Neo’s gravity defying bullet dodge. A movie that made a lasting impact on me.

Dylan Feldpausch of Chicago:

It epitomizes the alienation of modernity through a (literally and figuratively) subterranean queer lens. I remember watching it as a kid and being inexplicably drawn to its aesthetic, and only as an adult realizing how important it was to me as a nonbinary person — particularly the idea that you can imagine yourself into any identity no matter how inaccessible it may seem to you, and that your power in that identity comes from a strong commitment to your truest self.

Paddy Free of Auckland, New Zealand:

I was 10 in 1977, the perfect age for “Star Wars.” Walking out of “The Matrix,” I felt the feelings I’d hoped to feel walking into “The Phantom Menace.” 1999’s Great Disappointment and 1999’s Great Redeemer.

Drama. Drama. Drama.

Kevin Hengehold of Seal Beach, Calif., on “The Sixth Sense”:

Not your typical ghost story, and I still watch it whenever I see it on. Fantastic in-depth acting led by Haley Joel Osment along with Toni Collette and Bruce Willis. “I see dead people” is a line that will live on long after I’m gone … and I’m not planning on coming back to watch my wedding video …

Katie Robleski of Milwaukee on “Magnolia”:

I’m glued to the screen in a dark theater as Aimee Mann’s “Save Me” swells. John C. Reilly quietly delivers his monologue until Melora Walters breaks the fourth wall (and her gut-wrenching pain) with that hopeful smile — cut to black (and to my tears rolling with the credits). Perhaps being 19 made all the difference, but everything about “Magnolia” — Tom Cruise, full cast breaking into song, raining frogs, and 3-hour runtime included — completely changed cinema for me. I miss that era.

Zac Oldenburg of San Francisco on “Eyes Wide Shut”:

My memories started on a 4:3 aspect ratio DVD, but the film became a revelation once I saw it in a theater. Kidman is alluring on every level, and Cruise gives himself over to Kubrick in a way he has never done again for a director. It’s just an incredible film that sends Kubrick out on a high note.

Alex Arroyo of Littleton, Colo. on “Fight Club”:

I remember I was in junior high, a group of friends and I going to watch it in theaters. We were so pumped afterward, we just wanted to start our own fight club … we never did though; we were kinda nerds. But the idea of someone being so over all of the daily, typical BS and willing to do something to change it all, gave me hope and kinda made me feel like a badass for watching it.

Dana Jacoby of Cotati, Calif., on “American Beauty”: