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Best Film of 1999?

January 28, 2024 Jordan Ruimy

I highly recommend Brian Raftery‘s book “Best. Movie. Year. Ever: How 1999 Blew Up the Big Screen” which has been in bookstores now for over four years, but I finally got around to reading it recently. It reignited a conversation around 1999, maybe the best year at the movies … ever?

Vulture ran an entire chapter from the book on “Eyes Wide Shut.” It gives a good example of the style and scope of the book. And so, the inevitable question one must ask is this: Are we heavily overhyping 1999? The short answer is no.

Being John Malkovich, Election, The Matrix, Fight Club, American Beauty, The Limey, The Sixth Sense, Magnolia, The Straight Story, Eyes Wide Shut, Three Kings, The Insider, The Blair Witch Project, Bringing Out the Dead, Boys Don’t Cry, Go, The Iron Giant, Toy Story 2, Topsy-Turvy, All About My Mother, South Park, Office Space, The Talented Mr. Ripley, Run Lola Run, Princess Mononoke, American Pie, Bowfinger, Sleepy Hollow, The Hurricane, Dick, 10 Things I Hate About You, Arlington Road, Man on the Moon, The Dreamlife of Angels, Romance, Payback, Limbo, Rosetta, Dogma

The result was a highly influential set of films that would not only change filmmaking, but also set the tone for the 21st Century. It was a watershed moment, but people seem to also forget that was the same year “The Sopranos,” maybe the best TV series ever made, premiered on HBO.

Roger Ebert summed up the year pretty welll:

The Telluride and Toronto festivals had already started lobbing in great new films, and by the time I saw "Being John Malkovich" and "Three Kings" early in October, it was clear that Hollywood's hounds of creativity had been set loose and were running free. The last four months of 1999 were a rich and exciting time for moviegoers--there were so many wonderful films that for the first time in a long time, it was hard to keep up.

So, no, we are not overhyping 1999. It truly is the bees knees. Best movie year ever? Possibly. Is there any other modern-era year that evm came remotely close? Maybe 2007.

However, for all the glorious write-ups that 1999 keeps getting, there isn’t necessarily a clear consensus as to what was the one film that defined that movie year. Maybe because it’s a really tough choice. At least in 2007, the consensus could narrow it down to three films: “There Will Be Blood,” “Zodiac,” and “No Country For Old Men.” That’s not the case with 1999.

If you had to narrow it down to just a single seminal film from 1999, what would it be? The contenders seem to be too many. What one film defined the greatest movie year?

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