20/20 Hindsight: The Best Movies of 1999

As the 90’s came to a close, we got some of the best movies of the decade which, in many ways, were emblematic of the kinds of features we’d come to expect from Hollywood and beyond.  The rise of J-Horror, the retroactively disgusting presence of Kevin Spacey, the promising (but ultimately impotent) rise of Kevin Smith and the continued success of Pixar all served to cap off the century, producing the whole decade in miniature for us to watch and reflect on.

10. American Beauty

It’s easy to forget — and oh-so-very unfortunate in hindsight — just what a big deal Kevin Spacey was in the 90’s.  I mean, it’s not like his star had dimmed considerably leading up to his career-ending sexual scandal, but he was indominable during this decade.  Even in movies that were just passingly good, he was always reason enough to watch it when all was said and done.  Now, American Beauty is more than just ‘passingly good.’  Especially for the segment of the US population it represented at the time of its release, it was an extremely good, if extremely White, movie.  Despite its obvious top-down qualities, the movie today reeks irreconcilably of privilege and is caught in the crossfires of the Harvey Weinstein and Kevin Spacey Sex scandals.  Honestly, at this point, I can’t wait to find the exciting, previously unseen movie from this year that will bump it off of this list for good.

9. Dogma

Kevin Smith is a fascinating director, whose career’s arc is bound to be a subject as long-running as this retrospective series of articles.  Early Kevin Smith was interesting and ambitious in a way that stands out not just within his filmography, but within the decades that they were set.  Later Kevin Smith is polished but so inanely insular that few outside of his closed circle of hyper-devotees can even begin to appreciate them.  And while Clerks (1994) is a great movie that mostly holds up well after everything once unique about it has been cannibalized by the larger film industry, to my mind Smith’s work never got any better than Dogma: a raucous, ritiously funny and smarter-than-you-think religious spoof about a pair of angels who try to rules-lawyer their way back into Heaven after millennia of exile.  It’s fun, funny and somehow manages to play a literal poop demon completely straight: all in all, everything one could possibly want out of the directing half of Jay and Silent Bob.

8. The Iron Giant

I know it was easy to miss over the holiday break, but did you see Bumblebee (2018)?  Finally, an amazing Transformers movie whose action you can easily make sense of on-screen and whose Human characters are actually interesting enough people to star in the movie that they’re a part of.  After more than a decade of Baysplosive disappointments, it was unbelievably satisfying to sit down and watch the kind of movie we should have been getting all along.  The thing is, though, that we’ve been living in the world of Bumblebee for going on two decades now, only back then we called it The Iron Giant.  Coming in hot with everything that made its name-brand imitator so show-stoppingly excellent — interesting Human characters, an endearing alien robot, top-notch action and amazing visuals — it does so without the added baggage from being based on a series of glorified action figure commercials.  In as much as it was about a boy and his badass alien robot friend, it took hard stances against the social ills of the time period in which it was set (which very clearly act as analogs for the then-modern day equivalents), and can’t help but bring with it that much more charm, grace and inventiveness.

7. Audition

By now a movie whose grotesque reputation is far better known than the movie itself, it would be easy to assume that shock-and-awe torture porn was the only thing that this singularly Miike-directed movie has to offer.  And, even on the first watch, you might be tempted to give into those presumptuous impulses.  But Audition is about so much more than one pitiable man being vivisected by a vengeful lover.  At its core is the systematic abuse that many women must necessarily endure their entire lives: the internal wounds, scars and traumas that can warp a seemingly idealistic young woman into the monster stalking men’s fantasies.  There is a rich and prescient center to this unassuming horror movie, and one that deserves considerable reevaluation from those who dismissed it outright at first glance.

6. The Boondock Saints

Sometimes, though, there isn’t really anything deeper to a movie.  Sometimes, everything is surface-level.  And sometimes that’s perfectly okay.  In this modern-day reimagining of Death Wish (1974), the far-flung murder of Kitty Genovese inspires a pair of Irish American brothers to take their murderous talents to the organized crime syndicates that plague their city.  Featuring star-making turns for the roguish brothers and an especially bizarre turn for Willem Defoe as the detective simultaneously drawn to stop them and admiring their no-holds-barred approach to justice, it’s little more than a series of eye-popping imagery, endearing character moments and over-the-top bloodshed.  It leaves everything on the wall and nothing to chance, and every last second of it is amazing.

5. The Sixth Sense

It might have been dark goings for a while there — decades, in fact — but the fact of the matter is that M. Night Shyamalan is a remarkable director when he both wants to be and is given material worthy of his time.  Consumed by ego, plagued by studio mandates and oftentimes just plain not caring what he ultimately puts out, the Shyamalan of years past has been consistently one of the worst filmmakers working in Hollywood.  But starting with Split (2017), we were reminded of exactly what made us fall in love with him in the first place.  The Sixth Sense is a slow-burning horror-drama from whose DNA movies like Hereditary (2018) would eventually be birthed.  Famous for its “I see dead people” premise and twist, the movie holds up all these years later not because a young director momentarily pulled the wool over our eyes, but because of his careful attention to craft and detail that made it subsequently hold up over all those countless rewatches.

4. Being John Malkovich

There’s no doubt that this, more than any other movie on this list, will prove to be the most contentious: not the Japanese proto-torture-porn, not the divisive machinations of Kevin Smith, not the retroactively grotesque movie starring Kevin Spacey.  Even though people love to say that they’re head-over-heels for interesting, original and well-made movies, when something crosses the line into actually being weird, all its would-be supporters are never anywhere to be found.  Think of movies like Sorry to Bother You (2018) or Eraserhead (1977), cult-at-best oddities that never caught on with the larger public that never-the-less keeps demanding “original” movies.  Being John Malkovich, a movie that unflinchingly lays out its premise in its title, is that exact kind of movie, and one that everyone who claims to love original content owes it to themselves to see at least once.

3. Fight Club

Like Rick and Morty and A Clockwork Orange (1971), Fight Club is a movie that ultimately proved to be a terrible satire.  Don’t get me wrong, the movie is incredible, and sitting with it on its own terms and a thoughtful mind makes its naked attack on the toxic masculinity of its protagonists inescapably obvious.  The thing is, though, that the kinds of people that it was hellbent on satirizing didn’t realize what it was trying to do.  It went straight over their heads, became their unflinchingly favorite movie and inspired actual, honest-to-God fight clubs to crop up throughout the country.  It’s even where we get the derogatory use of “snowflake” from.  Fight Club was an air raid siren blaring as loud as it could, and we somehow lacked the wherewithal to listen.

2. The Matrix

To some degree, The Matrix has the same kinds of problems with Ghost in the Shell (1995) and Clerks do: everything that made the movie unique in the first place has long since been cannibalized by the Hollywood machine and been put to use in far worse, far less interesting types of stories.  It’s become its own sort of cliché and its hard to simply engage with the movie on its own terms anymore.  And yet, we’re still watching The Matrix.  Two terrible sequels, one in-development reboot and a couple decades later and The Matrix is still mandatory viewing for action and sci-fi junkies.  It, in fact, has simply become more interesting as the years have gone on and the internal lives of his trademark siblings have come to the fore.

1. Toy Story 2

They always say “if it’s not broke, don’t fix it,” and yet if Pixar followed that advice we never would have gotten the best movie in the long-running animated franchise.  While I appreciate the bold new approach that the first Toy Story (1995) represented and the thoroughly satisfying denouement that Toy Story 3 (2010) improbably proved to be — to say nothing of how fascinating the upcoming Toy Story 4 (2019) appears to be — my heart was always in this second installment.  For one, I always felt that it was the hands down funniest of the lot, which carried through to a fun new cadre of colorful characters and the most action-packed plot of the series.  But what’s more is that this movie intimately understands the core crises of these movies: not one of magical realism or even friendship, but of aging — of growing up and out and old and having to confront that at every turn.  We got that in the first movie when Woody had to contend with no longer being Andy’s favorite and again in the third when Andy grows up to the point that he no longer needs all of his old childhood friends.  But it is in this second movie that it hits us hardest, when Woody realizes the inevitability of the third movie and has to individually come to terms with his own mortality.  The primary arc of the third movie wasn’t as powerful because it had already been done before here a decade prior.

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