Right now it is hard to remember but there was a certain glorious optimism that surrounded the year 2000. We were living in that pocket between surviving the overhyped threat of Y2K and the tragic events of 9/11 a year later that would irreparably shatter our collective global. Coming off the relatively prosperous 90s, I remember staring at a new millennium as a teenager with seemingly endless possibilities ahead which was both exciting and terrifying. How wonderfully quaint.

YEAR AT A GLANCE

U.S. Domestic Box Office Top 10 (in millions):

1. How The Grinch Stole Christmas ($260.0)
2. Cast Away ($233.6)
3. Mission: Impossible II ($215.4)
4. Gladiator ($187.7)
5. What Women Want ($182.8)
6. The Perfect Storm ($182.6)
7. Meet The Parents (166.2)
8. X-Men ($157.3)
9. Scary Movie ($157.0)
10. What Lies Beneath ($155.5)

Hollywood seemed to view that new reality of open possibilities with a similar mix of fearful trepidation and foolish excitement resulting in a very weird year in movies. This is the year where the top movie was How The Grinch Stole Christmas, which perfectly anticipates a Hollywood turning to already established intellectual properties instead of original work. Gladiator, the best picture winner, tried to revive the sword-and-sandal genre and harkened back nostalgically to the golden age of Hollywood. Disney ended their unbroken streak of traditional animation by producing the computer-animated misfire Dinosaur. The horror-comedy Scary Movie debuted and in trying to make fun of Scream, itself a satirical (yet cleverly so) look at the slasher genre, anticipated a much more cynical age of comedy. It is a year where the biggest summer drama was A Perfect Storm because we could hardly imagine a greater tragedy that a fishing boat crew lost at sea. And 20th Century Fox took a gamble and dared release a big budget movie based on a comic book called X-Men (albeit stripped of most of its comic-book elements), a move that paved the way for the much more monolithic box-office landscape we have now. The movies of 2000 seem to perfectly reflect a culture that was ready for the brand-new but was trapped by the ennui of not knowing what that new would look like.

Oscar Best Picture Nominees: Chocolat; Crouching Tiger, Hidden Dragon; Erin Brockovich; Gladiator (WINNER); Traffic.

Apart from Chocolat helmed by Johnny Depp (yikes), whose presence here can easily be explained by the blatant campaigning from its producer Harvey Weinstein (double yikes), all the movies present here are surprisingly solid choices (if we accept that the Oscars frequently never actually land on the best movie of the year and our best hope in any given year is that they actually nominate and award movies that could be one of the best of the year). Gladiator‘s win is not exactly inspired but it is hardly surprising. Crouching Tiger, Hidden Dragon is the obvious winner of the “happy to be nominated” award as, twenty years before Bong Joon-Ho’s Parasite shocked us all and actually won the top prize, the mere fact that Hollywood would even look beyond the English-speaking world during awards season was the definition of novel behavior. Meanwhile Steven Soderbergh’s phenomenal achievement of getting two movies nominated for Best Picture probably doomed both Traffic and Erin Brockovich as it split the vote, leaving the sandal-clad Russell Crowe as obviously the last one standing.

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25. SEXY BEAST dir. Jonathan Glazer

Unfortunately for Brad Pitt and Guy Ritchie’s Snatch, there was only space for one British gangster movie and that spot was always going to go to Jonathan Glazer’s stunning debut Sexy Beast. It helps that unlike Snatch, this movie actually features some British luminaries as the leads, each putting in some excellent performances whether it is Ray Winstone as the retired gangster living in Spain who is forced to do one last job, Ian McShane as Winstone’s manipulative boss who twists Winstone’s arms to come out of retirement, and a crackerjack Ben Kingsley as the ultimate sociopathic wildcard who lights this tinderbox on fire.

24. BILLY ELLIOT dir. Stephen Daldry

Billy Elliot is about two teaspoons of sugar away from being saccharine sweet and nauseatingly so. Yet it is precisely because it toes the line so expertly that the movie instead is an effortless, if completely unsurprising, joy to watch. Twenty years on it is all to clear that we weren’t presumptive in naming Jamie Bell’s performance as revelatory as he anchors this conventional story about a boy in a working class British mining town who literally wants to dance his way out of the slums, while Julie Walters (of pre-Mrs. Weasley fame) is an absolute delight as Billy’s reluctant dance teacher. Would that more obvious Oscar-bait be as entertaining as this.

23. ITALIAN FOR BEGINNERS dir. Lone Scherfig

Like Agnes Varda with the French New Wave, it took a woman, in this case Lone Scherfig, to realize that the austere principles of the Dogme 95 movement need not be confined to a (primarily male) depressive worldview but could instead be the basis of a light-hearted romantic comedy. Italian for Beginners follows a widowed pastor newly-arrived in a Danish town who decides to join up a local Italian class with some of his fellow parishioners who may or may not be attracted to each other. The end result is a romantic comedy that is equal parts understated and heartwarming.

22. BATTLE ROYALE dir. Kinji Fukusaku

I remember how cute it was when people in the media were falling head-over-heels trying to describe their discomfort at the child-related violence in The Hunger Games, as it was clear they had not seen and couldn’t possibly imagine the carnage that was wrought years earlier in Battle Royale. Deservedly earning its “R”-rating, Battle Royale pitted a class of middle-school students against each other in a fight-to-the-death competition for the amusement of a totalitarian government, and unlike, the PG-rated Hunger Games, fully embraced the moral dilemma of that premise to monstrously horrific effect.

21. GLADIATOR dir. Ridley Scott

It is fairly impossible for me to evaluate this movie objectively since it was the first real “grown-up” movie I explicitly sought out in the theaters, and as a result was also the first movie that I actively was pulling for to win the Best Picture Oscar. And given that I was a heterosexual male, it was inevitable that I would find the sword-and-sandal action fare and the Russel Crowe-led speechifying intoxicatingly compelling. Meanwhile I spent most of the 2010s thinking the movie was overrated and the epitome of middlebrow Oscar-bait. Neither one of those two extreme views are correct, its place here seems just about right.

20. HIGH FIDELITY dir. Stephen Frears

Twenty years ago it was easy to fall in love with Rob Gordon (John Cusack), as his quirky, sensitive, and intelligent representation of the male personae seemed a world away from the pre-packaged and ultimately reductive view of male-hood shoved down the throats by turn-of-the-century pop culture. Now it is easy to hate his snobbish too-cool-for-school attitude as the inverse of a similarly toxic masculinity that seeks to canonize greatness while mocking those who don’t conform to their wisdom (he is also easy to hate because, frankly, his portrayal of an amateur critic with strongly held views of what is great and what is not hits a little to close to home for this blogger). Of course thankfully it seems at least the filmmakers are at least semi-aware of this problem and are smart enough to litigate Cusack’s character and those of their ilk, which is solely why it makes this list at all.

19. GEORGE WASHINGTON dir. David Gordon Green

David Gordon Green’s debut is still impressive twenty years later, telling the story of a group of teenagers, one sharing the name of the founding father of the country and wears a football helmet to protect his skull, symbolically living out the last summer of their innocence. Taking his cue from his non-professional actors, Green languidly lets us simply hang out with these poor black and white kids as they aimlessly wile the endless days of summer away building up nothing but their firm bonds of friendship with one another; bonds that are put to the most horrific of tests when one of them ends up dead.

18. THE GLEANERS AND I dir. Agnes Varda

Spitting in the face of the adage “an old dog can’t learn new tricks,” the French New Wave legend Agnes Varda took one look at the advent of digital video cameras and, rather than see it as the death of her industry, saw nothing but the chance to reinvent herself and reinvigorate the next two decades or so or her long career. Handheld digital camera in hand, Varda follows several groups of gleaners as they hunt for food all across the French countryside where the relatively cheap cost of video gives her the freedom to pursue her curiosities and in doing so reveal her own empathetic heart in ways traditional filmmaking could not afford to do.

17. BEST IN SHOW dir. Christopher Guest

Making fun of eccentric subcultures like the world of professional dog-showing is in some ways, an extremely easy thing to do. What Christopher Guest and his troupe manage to do in this movie that separates them from most satirists however is to infuse these larger-than-life ridiculous people with a degree of warmth and humanity so that, in spite of ourselves, we end up rooting for them even as we laugh at them. It also helps that Best of Show also lampoons dog lovers and dog owners, a gigantic subset of the population so it never feels like Guest is punching down but rather is laughing at the universal absurdity that is our affection and devotion for our mutts.

16. CAST AWAY dir. Robert Zemeckis

Of all the movies on this list, Cast Away has possibly aged the best, if for all the wrong reasons thanks to this infernal pandemic. While the parallels of seeing Tom Hanks finding himself isolation on a deserted island in the same year that we waited worriedly while Hanks recovered from COVID-19 in isolation is uncanny, Cast Away is also prescient in morehorrific ways. All of a sudden, we are all faced with the reality that like Cast Away’s Chuck, we have found all of our exacting plans laid to dust as we (hopefully) sit in our own personal islands at home waiting desperately for our lives to start up again. Even Wilson, Chuck’s inanimate ball friend, seems less of an implausible notion as we live desperately attached to our phones as our only outlet for our innate desire for human connection. Good times.

15. THE EMPEROR’S NEW GROOVE dir. Mark Dindal

Disney’s big splash this year was to release the computer-animated Dinosaur, a big budget sprawling special effects extravaganza that ended up being wanting in the story department. Meanwhile their other animated feature The Emperor’s New Groove, an almost shelved traditionally animated film with a troubled development turned out to quietly be one of the best they have ever produced. The fact that this is also the movie that succeeded by ditching its original epic premise (and with it, an entire Sting-produced soundtrack) in favor of madcap hijinks and pratfalls more associated with their former rivals Looney Tunes simply adds to strangeness of this movie’s success.

14. TOGETHER dir. Lukas Moodysson

The key to good satire is to, at some level, love the thing you mock. This is precisely what Lukas Moodysson does with his portrait of a 1970s hippie commune, where with pinpoint accuracy he reveals the inner contradictions and human weaknesses of a group of people utterly convinced of the wrongness of conventional life, but not quite able to figure out how to forge on to their new paths. And yet with that same precision Moodysson also narrows in with admirable affection on the beauty of the people living within and the beauty of their pursuit to reinvent themselves and imagine a better way of life, forged in the spirit of their shared community.

13. LOVE & BASKETBALL dir. Gina Prince-Bythewood

Sports and romance are two movies genres filled with overused cliches, which makes it all the more astonishing that Love & Basketball manages to combine the two effortlessly without ever once feeling formulaic. Credit of course needs to go to Sanaa Latham and Omar Epps who bring such a believable and incredibly nuanced humanity to Monica and Quincy, the two best-friends/rivals/lovers who occupy the heart of the story. But truly this is a triumph for writer-director Gina Prince-Bythewood who balances their love story with tenderness and sophistication; she brings a much needed and sorely underrepresented window into African-American life in this, her incredibly impressive debut. Oh, as a bonus, it also just happens to quietly feature one of the best soundtracks of all time.

12. CHICKEN RUN dirs. Nick Park and Peter Lord

Stop-motion animation is an act of tedious love even when in short-form, so the thought of first feature-length effort from Nick Park and Peter Lord is in some ways insane. But for their first feature to be a poultry-based gender-flipped remake of The Great Escape in which the British prisoners are replaced a group of hens and the cocksure Steve McQueen replaced by the, well, rooster Mel Gibson is such a shoot-for-the-moon effort that it cannot help but succeed. It helps of course that Park and Lord do not lose the focus that was so apparent in their Wallace & Gromit shorts and instead fill this movie with such hilarious wit and Rube-Goldberg machine comic timing that they make it easy to forget that you are, in fact, watching clay dolls.

11. ERIN BROCKOVICH dir. Steven Soderbergh

Erin Brockovich is an exquisite example in the woefully underrepresented film genre of “competent people doing their job extremely competently”. There is something inherently satisfying in seeing Brockovich, portrayed by a Julia Roberts at the top of her game, effortlessly take to the job of a paralegal as she outsmarts the powerful energy company in the major class action lawsuit her clients are bringing against them. This movie also serves as the perfect apex for Julia Roberts, who in many ways the definitive star of the 90s in which she had eight movies cross $100 million in the box office. So many times the Oscars are awarded to the right actor but for the wrong role; fortunately this isn’t the case here

10. O BROTHER WHERE ART THOU? dirs. Ethan and Joel Coen

There is a phenomenon with most of the Coen brothers’ movies where the initial viewing of their work often leaves the viewer feeling slightly underwhelmed and it is only upon multiple rewatches that you begin to understand just how great and deep their work actually is. O Brother, Where Art Thou? suffers from the opposite problem because when I first saw this movie I was blown away by this zany and funny adaptation of The Odyssey that transports its heroes from mythical Greece into the deep south (and like everyone else I was obsessed with the soundtrack). Subsequent viewings however have revealed little depth behind the screwball nature of its surface, which should take away nothing from the fact that it is still a pretty wonderful surface.

9. CROUCHING TIGER, HIDDEN DRAGON dir. Ang Lee

This movie belongs on the list for the way it made international cinema – so long the realm of art-house obscurity – mainstream. In many respects the movie should not have worked as a crossover success seeing as the wuxia genre is one of the most culturally-specific genres out there. But Ang Lee succeeds because he unapologetically refuses to compromise on the bombastic and operatic storytelling beats of the genre, and instead takes the additional budget provided to him by his Hollywood financiers and puts it onto the screen, creating a movie that is as gorgeous to look at as it is wondrously melodramatic.

8. BAMBOOZLED dir. Spike Lee

After a decade in which Spike Lee consistently delivered excellent movies and yet still found little to no financial support to fund his projects (including the lack of studio backing for his masterpiece Malcolm X and failure to get a Jackie Robinson biopic off the ground), he turned his acerbic wit towards the systemic racism surrounding the entertainment industry to explosive effect. This satire about a Black TV writer (Damon Wayans) who develops a minstrel show as a protest against his networks resistance to his desire to portray Black people in positive and intelligent scenarios is rapid-fire and pitch-perfect; the only thing keeping it from being a laugh riot is the uncomfortable precision and righteous anger with which Lee skewers the industry and by extension us, the complicit audience. A (mostly white) critical community labelled the film’s message unnecessary in our supposed enlightened age. I think today we can agree those critics were wrong.

7. AMERICAN PSYCHO dir. Mary Harron

Adapting Brett Easton Ellis’ novel about a yuppie misogynistic serial killer was always going to be a delicate task, and thus it is somewhat fortunate that the project landed at Mary Harron’s feet. Where 1999’s Fight Club suffered because director David Fincher couldn’t decide if its protagonist was meant to be revered or mocked, Harron has no such qualms with Patrick Bateman (Christian Bale). With Bateman she inadvertently and prophetically creates the definitive portrait of toxic masculinity almost twenty years before we collectively woke up to its destructive power. The fact that Bale’s Bateman clearly became a building block for his creation of his own Bruce Wayne which in turn made a bunch of fanboys wish for their comic book heroes to be “darker” shows that we all collectively missed Harron’s satirical and disturbing joke.

6. TRAFFIC dir. Steven Soderbergh

In a classic case of having too much of a good thing, Steven Soderbergh’s incredible achievement of being only the third person to have two of his movies nominated for Best Picture in the same year probably doomed his chances of nabbing the big prize (even if he did manage to win Best Director for Traffic). Here his tower-to-trench view on the illegal drug trade is a damning portrait of the lure of riches that makes any real effort to stop its proliferation such a hopeless cause in a country where capitalism one of its key virtues. Of course what makes the movie so powerful is that Soderbergh resists editorializing and preaching; his restraint means we are forced to come to our conclusions ourselves.

5. ALMOST FAMOUS dir. Cameron Crowe

This is an instance in which all the pieces serendipitously fell into place to craft the near-perfect movie. Patrick Fugit’s performance as the teenage William on his quest to be a music writer constantly oscillates between being believably naive and comically overacted but it works because it perfectly fits in with his character who is desperately trying to act older than he actually is. Meanwhile Kate Hudson’s future mediocre performances highlight that her Penny Lane miraculously took advantage of all of Hudson’s strengths as an actress while hiding her limitations. The band Stillwater surprisingly plays music good enough to be pleasant to listen to while being middling enough to believably make them a band with a quick rise and fall. Only Philip Seymour Hoffman gives the kind of consistently flawless performance that we knew he was capable of (in another painful reminder that his career was cut too short). The rest of Cameron Crowe’s middling career after this reminds us that Almost Famous was truly lightning-in-a-bottle.

4. MEMENTO dir. Christopher Nolan

In many ways Memento is the touchstone to understanding the rest of Christopher Nolan’s impressive oeuvre, establishing so many of the hallmarks that would become his calling card. Most obviously there is his penchant for juxtaposing a fairly objective camera with the most unreliable of point-of-views – here in Memento it means that Leonard Shelby’s (Guy Pearce) journey for revenge is on the surface easy to follow and yet always slightly out of reach. Then there are his experiments with cinematic time, which in later films can come across as cute because they become reductionistic mystery box lenses for fans to uncover his more bombastic and epic tales; in Memento the smallness of the story feels refreshingly intimacy while the relatively simple time-trick Nolan pulls here makes each viewing of the movie feel like a puzzle where the pieces increasingly fit. Also on an unrelated note, where the heck did Carrie-Anne Moss go?

3. YOU CAN COUNT ON ME dir. Kenneth Lonergan

Nothing about You Can Count On Me is new or groundbreaking, as we follow one woman who finds her life disrupted when her drop-out younger brother comes to visit in her small town. But it is the testament that sometimes all you need for a fantastic movie is to get all the fundamentals spot-on. It starts with the screenplay by director Kenneth Lonergan, who bravely refuses to go for cheap sentiment or flashy storytelling and instead seems content to allow us to sit with his very human characters as they quietly and openly navigate the tender but fraught waters of their relationship. And then there are the tour-de-force performances of the two leads, with Laura Linney as Sammy perfectly embodying a tender and empathetic soul who nonetheless finds herself at the end of her rope, while Mark Ruffalo walks a delicate balance as Terry, as someone who is irresponsible but tender-hearted, whose unpredictability brings life to Sammy’s home, but chaos. Together the two create the rarest of things: a realistic and affectionate portrayal of the sometimes touchy relationship that forms between adult siblings.

2. YI YI dir. Edward Yang

With an aching universality Edward Yang paints a picture of an ordinary middle-class Taiwanese family so completely that their plight is intimately familiar to us in Yi Yi, his last and arguably greatest movie. Yi Yi follows three members of this family through a year bookended by a marriage in the beginning and a funeral by the end, with just about every avenue of life explored within. In most movies that deal with the enormous scope of human experience there is a tendency to allow the search for profundity to weigh down the storytelling. What makes Yi Yi remarkable is that Yang finds buoyancy in his weighty subject matter, beauty in ordinariness, and manages to punch you in the gut in the most gentle way. Don’t let the movie’s 3-hour runtime fool you, this is an effervescent movie that breezes right by and leaves you wishing you could spend more time with these fully realized people. It is also perhaps indicative of the future of the 21st society as the top of this list represents movies made outside the hallowed halls of Hollywood.

1. IN THE MOOD FOR LOVE dir. Wong Kar-Wai

Let us be clear, there is a big gap between the top-two movies and the rest of the list and the distinction between number one and number two involves the splitting of the narrowest of hairs; these two masterpieces are still obvious choices for any shortlist for the best movies of the 21st century. Where Yi Yi reveled in the ordinariness of the human experience, In the Mood for Love is an intoxicating and hypnotic tale that dives deep into the highly subjective experience of unrequited love. In many ways this movie is the encapsulation of Wong Kar-Wai’s examination of the isolating nature of urban life. It is made all the more intense by two of the greatest Hong Kong actors ever to grace the screen in Tony Leung and Maggie Cheung who, like the best silent actors, say so much without barely speaking and convey in their gazes the epitome of romantic longing and (ultimately chaste) desire.