Decade-Dense: The 60 Most Memorable Films of 1999

Edited and Produced by Bill Gibron and Sarah Zupko

The difference in a decade can be remarkable. Imagine yourself at ten years of age, traipsing around the house without a care in the world. For you, the universe centers on nothing more than cartoons, sweets, and the horrific realities of life in the fifth grade. Now bump everything up. Suddenly, you’re 20, probably in college, and concerned more with drinking, dating, and the daily avoidance of any and all classes. Well, two out of three ain’t bad, especially when it comes to the maturation process. If anything, time can be our friend. It adds perspective, wisdom, a view enhanced by experience, learning, and an ability to really focus on the always broad big picture. This could explain the popularity and prevalence of “Best Of” retrospectives. It takes a while for the masses of media to narrow themselves down into something cogent and collective. And when they coincide with a birthday or anniversary, it makes the symbolism within the celebration all the sweeter.

Such is the case with our look back at the amazing movies of 1999. For those unaware, this was also the year of PopMatters‘ birth. Founded in October 1999 by editor and publisher Sarah Zupko, this online overview of the world of popular culture and media was there as DVD became a home video format phenomenon, as the dinosaur like CD gave way to the disc-less dimensions of the MP3, and as the Big Three broadcast giants started sweating under the commanding influence of hundreds of basic and pay channel alternatives. From competing styles to former and flailing superstars, PopMatters and its well-versed staff has been there through all the changes — most significantly in music and films. And as a means of making sense of our undying commitment to delving into and dissecting the many options out there, we figured we’d go back and uncover some of 1999’s most defining moments.

Therefore, in celebration of our decade at the cutting edge of everything cool, creative, and on occasion, crap, PopMatters offers the 60 Most Memorable Films of 1999. Actually, it’s 62. In fact, had we the time and the tenacity, we could have come up with 65, or 75, or 100 — it was just that kind of year. It’s as if the cinematic stars aligned to create a kind of critical karma for all things celluloid. Most eras, you’d be hard pressed to find 20 efforts to celebrate. But thanks to a combination of acumen, imagination, and individual drive, the motion picture artform of 1999 found itself with a glut of clear cut classics. Time-wise, it truly represents an embarrassment of riches. The same thing could be said for PopMatters. Day in and day out, there is so much fine writing, so much smartly penned scholarship and snark that any temporal treasure chest would be overflowing.

Sure, there are titles we left off, obvious commercial creations like The Mummy, Notting Hill, and Varsity Blues. We’ve also the good sense not to go back and “reconsider” garbage like Wild Wild West, The Haunting, or Deuce Bigelow, Male Gigolo. Yes, there are also glaring omissions. Galaxy Quest? MIA. Arlington Road? Close, but not included. From our group’s perspective, these are the movies that mattered, the calculated combination of sight and sound that left the most lasting and endearing of impressions. Argue over them, or suggest your own, but one thing’s clear — PopMatters shares a noble lineage with a lot of great movies. What better way to begin what is sure to be an extended commemoration. So sit back and enjoy PopMatters look at the 62 Most Memorable Films of 1999. It truly was a remarkable year on all accounts.

Bill Gibron