Now usually when a a year gets declared the “best year in movies” I roll my eyes simply because such a claim usually is highly subjective at best and hyperbolic at worst. And yet, 1999 inarguably deserves to be a contender in the conversation. Just to give you a taste of how great this year was here is a not-comprehensive list of good-to-great movies that did not make my list:

Fight Club; 10 Things I Hate About You; American Beauty; The Green Mile; Girl Interrupted; Audition; South Park: Bigger, Longer & Uncut; ExistenX; Ghost Dog; Bringing Out the Dead; October Sky; The Limey; Go; Mansfield Park; Following; Summer of Sam.

Included in those missing the cut are movies made by David Lynch, Martin Scorsese, Jim Jarmusch, Steven Soderbergh, David Fincher, Christopher Nolan, and Spike Lee, movies that in other years might be shoo-ins to the list. (Full Disclosure: I’m not a fan of Fight Club, so that was never going to end up on this list.) 1999 proved to be such a stacked year, providing movies that were immediate hits that have stood the test of time while still also including a host of great movies whose reputation have grown in the intervening decades. The blockbusters were spectacular, the indies were great too. Whatever fears, hopes, and anxieties were in the water at the end of the 20th century, it proved to be a fertile breeding ground for one of the best years in movies.

25. THE TALENTED MR. RIPLEY dir. Anthony Minghella

Part of the genius of The Talented Mr. Ripley is that it is almost impossible to be creeped out by Matt Damon, or at least the late-90s version of him. Thus when he inhabits the role of Tom Ripley, a hustler who first befriends and then nefariously steals his rich friend’s identity, he brings all of the goodwill he has earned in real life to make us root or at least sympathize with a character we should be actively rooting against. Under most circumstances, this ethical conundrum could be used as a litmus test for our own moralities, but thanks to the slick direction by Minghella and the effortless charms of Damon, we never really stand a chance to be lured to his side in this Hitchcockian thriller.

24. RAVENOUS dir. Antonia Bird

The very definition of an under-appreciated should-be cult hit. Nothing about this movie, about a Civil War-era Western comedy about some frontier soldiers who engage in cannibalism to give them vitality and life, signals that this movie should have ever delivered conventional success and indeed the movie flopped at the box office. But this weird and wonderful concept, starring Guy Pearce, Robert Carlyle, and David Arquette, should have guaranteed it instant clout amongst horror fans, especially since its batty premise was executed so perfectly with its perfect mix of camp and true terror. Consider this my public plea to elevate this movie to cult-hit status.

23. RATCATCHER dir. Lynne Ramsey

Placing you firmly on the ground of an impoverished corner in Glasgow, Lynne Ramsey’s debut movie is a stark and powerful gut punch of a movie about a boy and his desperate need to escape his circumstances. Unlike most coming-of-age movies, Ratcatcher seems almost pathologically incapable of painting a sentimental picture, instead providing a tough and stark picture of the kind of urban poverty that so often gets missed. And while Ramsey finds many a moment to give us glimpses of beauty, she never lets us forget that this beauty comes in spite of unjust poverty and the ugliness of humanity that allows that poverty to exist.

22. THE STRAIGHT STORY dir. David Lynch

In so many ways David Lynch’s career is defined by the ways he always pushes the boundaries of filmic language, often into new and exciting territory. This is why the Disney (!) produced The Straight Story is such an anomaly; a simple road-trip movie about one old man driving across several states in order to visit his dying and estranged brother. It is almost as if Lynch wanted to make a conventional movie just to prove that he could and the results are, if not the most exciting, certainly heart-warming and uplifting. While it is the rare Lynch movie that feels like it could have been directed by another person, that should not take away that The Straight Story, in its own simple and meditative way, is very good.

21. AMERICAN MOVIE dir. Chris Smith

The first time I saw American Movie, I simply assumed it was a mockumentary in the same vein as a Christopher Guest movie. Learning that this is in fact, a documentary about a real amateur director and his hapless quest to get his independent movie made, simultaneously made the movie more hilarious and more cringingly sympathetic. That this fascinating story about an artist trying his best to get his micro-budget horror movie shot and sent to Sundance for his big break in the same year that The Blair Witch Project made its buzzy debut at Sundance add a level of serendipity to the proceedings and also reminds us of the blessing and curse that is the American Dream: that an ambition that most people calls a “loser’s” path can quickly turn inspirational if, and only if, conventional success is found at the other end.

20. THREE KINGS dir. David O. Russell

It is somewhat surreal to see Three Kings, about a mad dash for stolen treasure by a quartet of insubordinate soldiers at the end of the First Gulf War, close to two decades after the Second Gulf War began and as of writing still continues. Created in that narrow gap of relative peace in 1999, it is surprisingly prescient about the connection between consumer culture and war. Of course you would be forgiven for not paying too much attention to that theme, especially when the performances of George Clooney, Mark Wahlberg, Ice Cube, and Spike Jonze are so captivatingly entertaining and the movie moves at such breakneck speed.

19. GALAXY QUEST dir. Dean Parisot 

Will Wheaton considers this the best Star Trek movie ever made and honestly, who am I to disagree with that sentiment. This Star Trek parody, that for legal reasons is clearly not a Star Trek parody, could have so easily taken the easy route in cruelly mocking the franchise and the fans who love it. Instead Galaxy Quest charts its own path by lovingly evoking the feel of the original Star Trek series while being self-aware enough to poke fun at the series’ more ridiculous edges. As an added bonus, in the intervening years this cast has turned from a solid line-up into a star studded one where previously top-billed Tim Allen somehow is the least illustrious of a bunch that includes the increasingly resurgent Sigourney Weaver, the multiple Emmy-award winning Tony Shalhoub, the franchise superstar (and taken from us too soon) Alan Rickman, and the somehow Academy-award winner Sam Rockwell among others.

18. THE BLAIR WITCH PROJECT dir. Daniel Myrick and Eduardo Sanchez

Though the movie’s phenomenal financial success is entirely due to its viral marketing campaign, there is also a sense in which The Blair Witch Project’s legacy has been hurt because it simply could not live up to the enormous hype. But now, divorced from its original release context, we can appreciate The Blair Witch Project for what it is: a groundbreaking movie experiment that paved the way for the found-footage genre, an incredibly restrained folk horror movie that understood the profound lesson that our imaginations are more frightful than anything a filmmaker could conjure, and a terrifying human document of how people break down when faced with their imminent mortality.

(FULL REVIEW)

17. BOYS DON’T CRY dir. Kimberly Pierce

Undoubtedly this movie, as much as its heart might be in the right place, is slightly outdated in its depiction of the LGBTQ+ community especially in casting the cisgendered Hilary Swank as Brandon Teena, a trans man who was brutally raped and murdered. That it is still this high on the list tells you how good Boys Don’t Cry is despite its dated flaws. Almost all of this is because director Kimberly Pierce refuses to turn this into a melodrama and instead starkly put us in the bleak frame of mind of what it meant to be transgender in America before anything close to the mainstream acceptance of the LGBTQ+ community had been achieved let alone any sophisticated public discussion of transgender identity could be had. And though Swank probably would not and should not get the role were it being cast today, it is undeniable that she is phenomenal in playing Brandon, putting a three-dimensional face to a sexual identity that long was merely the subject of public ridicule and vitriol.

16. SLEEPY HOLLOW dir. Tim Burton

Remarkably Tim Burton, a director famously known for his gothic aesthetic, has done very few pure horror movies. Sleepy Hollow reminds us how absurd that fact is, and that Burton should in fact do many, many more. Borrowing from classic slasher tropes but adding a whole bunch of wigs and colonial flavor, Sleepy Hollow is an effortlessly fun and terrifying romp. It also features the rare Johnny Depp performance that is simultaneously understated and highly stylized as the eccentric Ichabod Crane. And while Burton’s gothic aesthetic usually fits best when it is juxtaposed with conformist normality, it is thrilling to see Burton able to create a whole movie using that palate.

15. ELECTION dir. Alexander Payne

This tale, about the lengths to which an insecure man would go to undermine a powerful and ambitious woman, is one that has only gotten more prescient with age. Casting the “too-cool-for-school” Matthew Broderick as Jim McCalister, a grown-up and slightly washed-up Bueller-type was a special stroke of genius, simultaneously proving what a great actor Broderick can be when cast in a good role (and not, say, as a worm scientist hunting Godzilla). But Reese Witherspoon is the unquestionable star of this piece as Tracy Fleck, the ambitious student running for student body president. She manages to be both grating and likeable, with a ruthless streak that gives some merit to McCalister wanting to take her down even as it becomes clearly apparent that is an entirely unfair, and altogether sexist, stance for him to take.

14. OFFICE SPACE dir. Mike Judge

On the one hand this movie is a relic of the past, where the angst regarding a well-paying but meaningless job seems like a foreign concept in the age of the hustle economy and disappearing middle class. But what makes Office Space so bitingly and timelessly funny is that it is ultimately railing against the underlying cultural forces that would actively dehumanize the people who would work within its system and crush their spirit. And while this mostly male cast is each of them exceptional in their roles, Office Space is a reminder of what a phenomenal actress Jennifer Aniston is and how criminally underused she has been in her post-Friends tenure.

13. THE VIRGIN SUICIDES dir. Sofia Coppola

Most of our movies about teenage girls from the perspective of teenage boys decidedly came from the viewpoint of adult men projecting their adult sexuality onto their teenage selves (often in pretty gross ways). What makes The Virgin Suicides so vital and raw is that it is an adult memoir that corporealizes what it feels like to actually be a teenager and be confronted by the exciting and frankly frightening burgeoning of one’s own sexuality. This is a movie where the girls, on the verge of womanhood, are kept at a pedestal not because they are goddesses of male fantasy, but because as boys who barely know how to distinguish themselves from the gender expectations placed upon them they simply have no clue how to understand womanhood. The end result is a movie that is forever hypnotic, haunting, and mesmerizing; as impressive a directing debut as any.

12. MAN ON THE MOON dir. Milos Forman

Usually the appeal of a biopic (and one of the reasons it is one of my least favorite genres) is that it posits to peel back the curtain on a famous person so that we can get a better grasp on who they are and what made them tick. Man on the Moon somehow makes Andy Kauffman, the famously enigmatic stand-up comedian, seem even more obtuse and unknowable and is all the more compelling for it. Featuring an unbelievable performance by Jim Carrey (in a role that is both captivating and sad to watch now that we know it effectively “broke” Carrey to do it), it is a movie that, like Kauffman himself, demands you get on its specific wavelength before it offers up its pleasures. Rest assured, the effort to get on the wavelength is worth it.

11. EYES WIDE SHUT dir. Stanley Kubrick

Kubrick’s last movie is an interesting conundrum: it is certainly not the disappointment it was proclaimed to be when it first came out, neither is it the unquestioned top-tier Kubrick masterpiece some have come around to calling it years later. What Eyes Wide Shut is however, is incredibly compelling especially for the way it seems to chronicle the real-life dissolution of the real-life A-list power couple Tom Cruise and Nicole Kidman. Both of them give performances so convincing that we cannot help but intrude, making us feel both complicit and privileged because Kubrick, ever the master of voyeurism, has once again brought the private to light.

10. THE SIXTH SENSE dir. M. Night Shyamalan 

Yes, in many ways this movie is inseparably tied to its dramatic last-act twist and perhaps unfairly burdened by M. Night Shyamalan’s subsequent using the same last-act twist in his movies until it became self-parodic. But what sets The Sixth Sense apart from Shyamalan’s future projects is that it is a movie that absolutely earns its twist even in repeat viewings once the ending is known. Part of this has to do with Shyamalan’s restraint, keeping the movie at a muted energy level throughout and in so doing displaying an internal confidence of knowing his story will land. Part of that has to do with Willis, who sleepy understatedness is perfect for his role as a child psychiatrist. But the MVP is clearly Haley Joel Osment, who convinces you that he can indeed see dead people and turns in a mature performance well beyond his years, making The Sixth Sense endlessly rewatchable.

9. BEAU TRAVAIL dir. Claire Denis

Claire Denis’ impressive filmography is littered with characters filled with unspoken desires. In what might be her masterpiece Beau Travail, that unspoken desire is bitterness and envy as Sergeant Galoup (Denis Lavant), in charge of a French Foreign Legion outpost, finds his life disrupted by the presence of a new recruit Sentain (Gregoire Colin) who is winning the admiration of his peers and superiors with his selflessness. Jealous, Galoup plots a diabolical scheme to get rid of Sentain, an act of ugliness made all the more evil by its stark contrast to the beautifully lyrical and balletic way the story unfolds.

8. TOY STORY 2 dir. John Lasseter

Toy Story was a tale that answered the question “What if a child’s toys were alive?” with a childlike simplicity and was just about perfect in doing so. If the sequel had simply been more of the same it would have certainly been an acceptable, if not very creative, addition to the series (in fact that was exactly what Disney was hoping for with this movie originally set for a direct-to-video release). But what sets Toy Story 2 apart as not only a fantastic sequel but potentially the best in the series is that it took seriously the series’ founding question from an existential standpoint, infusing the story with a melancholic wonder that has permeated through two further sequels. Furthermore it also cemented Pixar’s storytelling DNA which would serve the studio well during its golden run in the 2000s.

7. TOPSY-TURVY dir. Mike Leigh

Topsy-Turvy‘s magic is found in the simple joy of seeing competent artists creating great art. This biopic about the famous theatrical partnership of Arthur Sullivan (Allan Corduner) and W. S. Gilbert (Jim Broadbent) peels back the curtain to show the many meticulous steps necessary to turn a theatrical idea into a full-blown play from the ground up. Along the way Gilbert and Sullivan butt heads, as all creatives usually do, on both issues personal and professional on the path to bringing their upcoming play The Mikado to life and in typical Leigh fashion, these conflicts are every bit as witty as they are thrilling. And with pain-staking detail we are exposed to just about every department in the theater company, each tasked with a problem that requires a creative solution. Certainly there are more thrilling movies on this list, but none more leisurely satisfying.

6. THE INSIDER dir. Michael Mann

The Insider comes at a critical time for its two stars. It catches Al Pacino just before he entered into his “manic Pacino” phase, thus capturing Pacino at his intense best with just the right amount of righteous energy thrown into the mix as the producer of 60 Minutes. Meanwhile this is a Russell Crowe just before the dual Oscar wins for Gladiator and A Beautiful Mind that for all intents and purposes announced his arrival as a A-list actor and meant he didn’t have to try as hard. In The Insider he is still hungry, and still trying, as the whistleblower in the tobacco industry who trusts nobody and is assaulted from all sides. In the hands of Michael Mann, The Insider has all the intensity and thrill of Heat but minus the literal firepower, thus perfectly representing an update to All The President’s Men for the end of the millennium.

5. THE IRON GIANT dir. Brad Bird

“You are who you choose to be.” Brad Bird’s first movie unfolds its rather complex message – that what we were made for doesn’t need to define who we could be – with remarkable childlike simplicity. The Iron Giant feels like an important milestone, coming at the tail-end of the Disney Renaissance and its all-encompassing hold of American animation in the 90’s while signaling the newfound depth in animated movie storytelling that would be the hallmark of Pixar’s golden run in 2000s (a run Brad Bird himself would be instrumental in forming). Apart from the storytelling there is the unique animation in this movie, which somehow manages to perfectly evoke a nostalgic past while seeming entirely new and unique. In other words, an instant classic whose reputation and worth has grown in the intervening years since its release.

4. ALL ABOUT MY MOTHER dir. Pedro Almodovar

The best trick that Pedro Almodovar pulls is that he manages to populate most of his movies with characters and situations so melodramatically outlandish that it would not look out-of-place in a telenovela but treats his characters with so much empathy and respect so you that you fail to notice the objective ridiculousness of their situation and are instead drawn in to unconditionally root for them. Nowhere was this more the case than in All About My Mother where Manuela (Cecilia Roth), a bereaved mother, journeys to Barcelona to tell Lola , a transgender woman, that the son they had together and kept a secret from Lola had recently died. Along the way a whole cast of characters of people on the fringes of society come across Manuela’s path leading to a story that dances effortlessly between being dark and depressing to buoyant and funny without ever descending into camp or parody. Almodovar doesn’t always get the balance right in his movies, but All About My Mother proves that when he does strike the perfect balance, his movies are almost unparalleled.

3. BEING JOHN MALKOVICH dir. Spike Jonze

Being John Malkovich is a wonderful paradox: It is a movie that whose concept is so out of left-field as to be almost alienating, but is so entertaining and darkly funny that you hardly notice the movie’s strangeness or are at least fully onboard for the ride. Buoyed by a great Charlie Kaufman script (probably the most consistently-exciting screenwriter of the last twenty years) and a pitch-perfect cast – led by possibly-best ever performances by John Cusack and Cameron Diaz (as well as a brave self-referential turn by Malkovich himself) – director Spike Jonze effortlessly creates the ultimate voyeur movie by showing exactly what it feels like to literally be in someone else’s head.

2. MAGNOLIA dir. Paul Thomas Anderson

Understandably a three-hour fantastical parable about a cast of mostly unlikeable people set in the banal suburban doldrums of the San Fernando valley where a (minor spoiler) literal plague of frogs proves the salvation for most of the characters is not everyone’s cup of tea. But if you find yourself being swept in its operatic flow, like I did, then it is truly a captivating experience. Magnolia is a movie about the harm we inflict upon children, whether physically or psychologically, and the way the harm we suffer as children shapes who we ultimately become. With a rogue’s gallery of phenomenal actors including Tom Cruise, William H. Macy, Philip Seymour Hoffman, Julianne Moore, and John C. Reilly among others, the movie certainly does not lack for compelling performances. And its parabolic message, about the importance of letting go, turns the movie into a bombastic epic that is as much rapturous as it is melancholic.

1. THE MATRIX dirs. Lana and Lily Wachowski

The Matrix is, to put it simply, cool – a quality many movies try and completely fail to attain but a quality the Wachowskis achieve effortlessly. Absolutely groundbreaking and breathtaking when it first came out, it is a testament that in the twenty years since very little has aged about The Matrix and the list of movies that have managed to surpass what The Matrix did, whether from a technical, action, or thematic standpoint, is very few. Under most circumstances pairing action with a mythology-heavy science-fiction story and a healthy amount of philosophy is a recipe for disaster and yet The Matrix works, because the Wachowskis prove so earnestly committed to the outlandish premise from frame one. It did for philosophy what Jurassic Park did for paleontology and, if imitation is the sincerest form of flattery, left a long trail of pop culture directly influenced by its undeniably coolness in its wake.

(FULL REVIEW)