20 Years Later: Reflecting on the Films of 1999


To the casual nostalgic, the year 1999 may be viewed as an existential tipping point. It was the final year in a relatively stable decade, one largely unmarked by war or social upheaval. Yet despite the booming economy and a relative lack of international tension, an unconscious feeling told many Americans that something was happening. As the days shifted inexorably toward the new year – and the literal once-in-a-millennium experience of seeing all the calendar’s digits change simultaneously – fears of the Y2K bug, and how it would impact a technological culture just acclimating to the strange and mysterious force of the Internet, gnawed at many an uncertain soul.

How much the fear and panic spurred on the late-‘90s cultural revolution, we may never know. But spurred it was, particularly on the screen. Not for TV, mind you, although there were certainly some impressive TV shows to debut that year (The Sopranos immediately springs to mind, as does a pair of other shows that I may have written a thing or two about). No, the major game-change occurred on the silver screen, as theaters nationwide exploded with some of the most colorful and innovative films in history.

You could argue that other years featured loftier filmic peaks, or more defining examples for individual genres. But perhaps no single year has featured as fresh and creative and “How did that get made?” a crop as 1999. And now, we finally have a book to celebrate and champion the cinematic joys of that incredible year.

Written by Brian Raftery, “Best. Movie. Year. Ever: How 1999 Blew Up the Big Screen” goes behind the camera, exploring 30 different films released during the final twelve months of the twentieth century. Enhanced by over a hundred interviews with both well-known and unfairly forgotten Hollywood alums, Raftery transports us back to the days of TiVo and Tony Hawk, Bill Clinton and the Backstreet Boys, to remind us what a thrilling and fertile moviemaking year it was.

Told in (mostly) chronological order, the book kicks off with the excellent Blair Witch Project, which premiered at Sundance in January of that year and soon worked its way up to a wide theatrical release. The story behind Blair Witch, a film produced on a $60,000 budget that defied all expectations to become one of the year’s biggest hits, sets an intriguing tone for the rest of the book, which explores films from every genre (and seemingly every well-known filmmaker) beneath the scorching Hollywood sun.

Want a dryly funny comedy about corporate America? 1999 gives you Office Space. A sci-fi action flick that raises questions about the nature of reality? Try The Matrix. How about a film that combines sci-fi and comedy and serves as a nostalgic time capsule in its own right? Hello, Galaxy Quest. Few years can claim to mix and match and subvert their genre expectations as well as this one.

Some of the year’s best films were helmed by first-time directors, including The Iron Giant (Brad Bird) and Being John Malkovich (Spike Jonze). Others saw the breakout of previously-unknown directors, like the M. Night Shyamalan, whose Sixth Sense became one of the most popular films of the year. A particular highlight of the period was the late-90s teensploitation boom, which kicked off in 1995 with Clueless and climaxed in the decade’s final year with cult classics like She’s All That, American Pie, and my personal favorite, 10 Things I Hate About You. (The teen comedy genre would continue chugging along for another few years, but by the time Not Another Teen Movie hit theaters in 2001, the bubble had clearly burst.)

What’s perhaps most interesting about the year 1999 in film is that – much like any other great year in cinema, or TV, or pop-culture at large – it wasn’t highly appreciated in its time. Inventive films like Fight Club and Election bombed at the box-office. The year’s Oscar field included largely forgotten flicks like The Cider House Rules, and the Best Picture award went to American Beauty a film that hasn’t aged well even once you get past the Kevin Spacey of it all. (It does get its own entry in the book.)

And the year’s most popular film was also, paradoxically, its most hated. The Phantom Menace shattered box-office records everywhere when it ended the 16-year Star Wars drought, yet the nascent online community tore it apart, and continue to mock its plot, dialogue, and CGI Gungan eyesores to this day. (Granted, some have now moved on to declaring that The Last Jedi is worse, but those people are sad and wrong.) Wisely, however, Raftery includes Phantom Menace in the book, as – despite its quality – no discussion of the year’s influence on culture would be complete without it.

Audiences of 1999 may not have appreciated the minor filmic Renaissance they were swept up in, but luckily for them, the year’s best movies didn’t simply evaporate. Many found dedicated fanbases on the home video and DVD market, with some becoming permanent staples of the online lexicon. (The first rule of Internet memes is: We do not talk about Internet memes.) Heck, many of the technological-based films of that year are even more relevant than they are now – with the issues of online culture more influential than ever, I’m sure some of us would be glad to step into the Matrix.

I fear that I’m stealing the spotlight by discussing 1999’s highs and lows – the book covers all that and more, with an abundance of eye-opening detail. There is no better way to appreciate the films of that incredible year than by picking up a copy. No better way, that is, than by watching the films themselves.

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