The 100 Best Movies of the 21st Century

(So Far)

A friend forwarded me the recent New York Times article featuring a list of the 100 best films of the 21st century, as determined by a poll of 500 directors, actors, and other Hollywood notables. I am not at all enthused by this list. I expected it to be pretentious, and it certainly is, but that’s fine. It would be weird if such a list weren’t full of films no one likes but knows they need to pretend to like lest they appear uncultured. No, it’s something else. It feels off to me, as if it were less a list of the best films and more a list of the films those polled wished to see represented on such a list. Rather than ranking films solely on quality, the ratings were weighted additionally, perhaps even primarily, by who made them, or why they were made, factors I don’t take into consideration when judging how good, or bad, a film is.

If you want to jump right to my list of films, be my guest. You can also view it on Letterboxd.

I hesitated to create my own list, because I find ranked lists to be useless, be they a list of films or local restaurants. They’re great food for “the algorithm,” but counterproductive otherwise. A ranked list of films is especially bad. Art, like a cheeseburger, is not meant to be competitive, and in a world where we already treat everything from dating to politics as if they were sports, I’d rather we didn’t keep score when it comes to movies. We already do, of course, whether it’s ranking films by their take at the box office or their “freshness” score on Rotten Tomatoes, but did I really want to participate in so Sisyphean an endeavor?

Another reason I didn’t want to make my own list is that I’m lousy at ranking things.

Even assigning a single film a rating is difficult for me, so you can imagine the trouble I have when judging one film against another. Like many cinephiles, I use Letterboxd to keep track of the films I watch. Each time I log a film, I’m prompted to give it a rating from 1 to 10 (from 1/2 a star up to 5 stars). I always give it my best shot, but invariably, when I look back at how many stars I’ve given a film, I find myself disagreeing with my own rating, especially when I see that rating in comparison to what I rated another film. I never feel confident choosing how many stars to assign a film, preferring instead to declare either “I liked it,” or “I disliked it.” That’s my rating system. Good or bad. No stars, no tiers, no hearts, no thumbs up or down; just “yes, good” or “ugh, bad.”

If pressed to compare two films I can sometimes tell you which I think is better, but once you throw a third one into the mix, I’m lost. Sometimes film A is better than film B, which is better than film C, yet somehow film C is better than film A. Now add another 97 films into the equation and it becomes an exercise in futility. Moreover, some films can’t be meaningfully compared. A superhero film or a slapstick comedy can be great, and even transcend its genre, but ultimately, it lacks the layers of a “serious” film, or god forbid an “arty” film. Does that mean such films don’t belong on the list? How exactly is one to compare The Hangover to Mulholland Drive? The latter clearly has far more for audiences to chew on, but is it necessarily a better film? If so, how much better? Can a Godzilla film or an Iron Man film even make a list of best films, or is there a point at which the scale between entertaining and thought-provoking tips away from “great film” into “fun movie” territory? I don’t think so, but I’m clearly in the minority, by a score of 500 to 1 it seems.

I believe that all films have the power to inspire or change us. We see ourselves reflected back at us from the screen, and read our own desires, fears, and sorrows into the stories we’re being told. That’s the power of film, and any sort of film can wield that power, be it a blockbuster or an indie shot on a shoestring budget.

More than anything else, it was that last thought that got me past my initial misgivings, and motivated me to create my own ranked list of the 100 best films of the 21st century so far. And, for the pedants reading, I’m going with the New York Times’ inclusion of the year 2000 in the 21st century. We all know that y2k was the dawn of the new century, not 2001.

What do I consider when ranking a film?

1. Entertainment— First and foremost, a movie must entertain me. I must enjoy watching it in order for me to consider it a great movie. That doesn’t mean it has to be a “fun” movie, or full of action. I enjoy slow-paced films, and films where nearly nothing happens. As long as the film holds my interest I consider it entertaining. I don’t need a happy ending. I love dense, dark films that are filled with symbolism. I also like movies that make me laugh. I rarely like action or horror films, but some such films have elements that elevate them into the “great movie” category, and I give every one of them a fair shake when I watch.

2. Emotion— I appreciate a film that moves me, and elicits an emotional response from me. Sometimes, powerful scenes can bring tears to my eyes. I know many people who claim never to have been moved to tears by a work of art, but I certainly have been. Tears are an extreme response, and only a handful of films have had that effect on me, but many films have given me chills, or filled me with great sorrow, or great joy, and I appreciate the skill required of a filmmaker to foster such emotions in an audience.

3. Cleverness— some films win me over with clever cinematography, others with complex plots. Lots of things can “wow” me when I watch, and I appreciate them all. Cleverness by itself isn’t enough to elevate a mediocre film to greatness, but it helps. Conversely, plot holes and lazy writing can doom an otherwise great film to mediocrity.

4. Great Moments— Howard Hawks once said, “a good movie is three good scenes and no bad scenes.” I agree with Hawks. Some films are okay for the most part, but there are a few moments so powerful that they lift the entire film to new heights, and I’m a sucker for those scenes. Give me a movie that’s good for the most part, and toss in a couple conversations that give me chills, and I’m sold.

5. My Opinion— When it comes down to it, this list is nothing more than the films I liked best. I’m not out to prove a point, or to say anyone else is wrong. These are the films that gave me the most joy when I watched them, and made me think about things in new ways.

And that’s it. Those are my criteria, these are my films.

Greg’s 100 Best Films of the 21st Century So Far

100. Pumpkin
Anthony Abrams and Adam Larson Broder (2002)

The film that barely made the cut, Pumpkin is an unusual movie, and I can’t think of any other film like it. Maybe its closest cousin is Heathers, but it’s more grounded, yet more unsettling, than that film. It’s both bizarre and sweet, simultaneously outlandish and utterly realistic. Mostly, it’s a story of an unlikely love affair, that feels not only likely but inevitable because of how skillfully it is handled. I’m going to avoid spoilers, and generally avoid plot summaries, as I go through these films, so I’ll leave it at that.

99. Brawl in Cell Block 99
S. Craig Zahler (2017)

If you can handle bloody violence in its most grim and unabashed form, give this film a go. Keep in mind that beyond all the stomped heads and stabbed bodies, this film is a study of what it means to be a man. Honor, duty, and sacrifice are the real topics being explored, and the prison setting is ultimately mere window dressing. It also works on a more surface level as the story of a man who has to get from point A to point B while facing seemingly unsurmountable obstacles. It excels in both arenas.

98. Secretary
Steven Shainberg (2002)

Secretary has quietly wielded its influence on an entire generation, yet still lives under the radar. James Spader, as at home playing a son of a bitch as a milksop, is in top form here, playing Mr. Grey (possible inspiration for another BDSM Grey??), and displaying at least 50 shades of dominance over Maggie Gyllenhaal’s Lee Holloway. I suppose you could say this film explores what it means to be a man in a very different manner from how Brawl in Cell Block 99 approaches the topic.

97. A Coffee in Berlin
Jan Ole Gerster (2012)

I have a nephew who is (was?) a filmmaker, and I’d sometimes text him ideas for movies he should make. My favorite idea I ever pitched him was “a movie where a guy wants a cup of coffee, but things keep getting in the way.” I came up with the idea after one too many days where I wanted a cup of coffee, but things kept coming up that prevented me from getting one. Imagine my surprise when I learned someone in Germany made my movie. It’s a light, charming, fun movie that I’d enjoy even I didn’t have the chance to write it myself.

96. Enchanted
Kevin Lima (2007)

The last great Disney film, Enchanted is a delight from beginning to end. It has plenty of Disney hallmarks— a prince and a princess, talking animals, an evil queen— to entertain kids, but with a bittersweet romantic story that will engage adults. It’s hard to fathom how the studio that produced this, and so many other classics, has fallen so far so rapidly.

95. Blood Work
Clint Eastwood (2002)

Clint Eastwood has remained remarkably consistent throughout more than half a century of directing films, and could realistically have 7 or 8 entries on this list. Blood Work hasn’t received the acclaim that so many other films of his have, but I love the film. It’s something of a hangout film, with lots of great dialogue and character interactions, and lacks the larger-than-life storyline that so many of his more revered films contain, but it’s something I can watch over and over. I have a distinct memory of the first time I watche it, during its theatrical run, and thinking “in real life, he’d grab a gun and go after that guy, but since it’s a movie he’ll let him go,” at which point Eastwood’s character popped open his trunk, pulled out a shotgun, and started blasting away at the villain’s car. That in a nutshell is why I love Clint Eastwood’s movies.

94. High Fidelity
Stephen Frears (2000)

Another movie where you feel like you’re hanging out with the characters while you watch. This film is the coming out party for Jack Black, and propelled him into the public eye, but it’s is filled with powerful ruminations and memorable one-liners. Few movies better convey what it’s like to endure a breakup than High Fidelity.

93. A Knight’s Tale
Brian Helgeland (2001)

The best movie Geoffrey Chaucer ever wrote, and one that transcended the fluffy teen flick it was likely meant to be. This is due in no small part to Heath Ledger, who elevated seemingly every film he was ever in. The film is at the same time a small story of a band of outcasts who form a friendship, and a larger than life tale of knights in shining armor, beautiful princesses, and one peasant’s attempt to crash the royal party.

92. Vanilla Sky
Cameron Crowe (2001)

Somewhat forgotten today, this is one of Tom Cruise’s finer films. It’s cerebral, but also entertaining, and never lets either of those aspects take center stage, preferring to remain a balanced entertainment. Best of all, it’s intelligent. It drops tiny hints here and there, and gives the audience just enough to keep them guessing before its wild denouement. And it features Cameron Diaz, so there’s that.

91. The Incredibles
Brad Bird (2004)

Who else misses Pixar, back when it was still Pixar? Will they ever again make a film on par with any of their pre-Disney efforts? From A Toy Story to The Incredibles everything they released back then seemed to be excellent. Since then, they’ve put out a few decent films and a whole lot of crap. This film, a comedic riff on the Fantastic Four, is non-stop entertainment and laughs for viewers of any age.

90. The Man from Earth
Richard Schenkman (2007)

A little-known film that I stumbled upon by accident, The Man From Earth packs a powerful punch. The few people I know who have seen it are ardent fans, and if you’ve not seen it, perhaps you will become one, too, if you watch. I won’t give much away, because part of the films power is the way it slowly unfolds its narrative, and will say only that it’s a dialogue-driven film that takes place almost entirely in one room, where a man slowly tells the tale of his long, long life.

89. Better Luck Tomorrow
Justin Lin (2002)

I’ve seen this only once, during its limited release some 22 years ago, but it has stayed with me. It’s intricately plotted, full of witty, funny dialogue, and an unflinching look at a different side of Asian-Americans than is typically presented in film. This is the story of a group of high-achieving, straight A students who dabble in crime, and end up accidentally on purpose murdering someone. Naturally, drama ensues. It’s loosely based on a true story. I had high expectations from Justin Lin after seeing this, but sadly I’ve disliked everything he’s done since.

88. The French Dispatch
Wes Anderson (2021)

Though not considered by many to be one of Wes Anderson’s better films, I kept finding myself unable to remove this from my list as I was compiling it. The Life Aquatic with Steve Zissou, Moonrise Kingdom, and Grand Budapest Hotel are all typically more highly touted films from Anderson, but one by one they dropped off my list quite early. This one lingered, and ultimately remained. It’s beautifully shot, and has one of the best opening sequences in the history of cinema, as we follow a tray of beverages and knick knacks from creation to delivery. It’s also a paean to the glory days of the printed word, something I miss dearly, with dialogue that flows from characters like prose from the pen of a master.

87. It Follows
David Robert Mitchell (2014)

I’m very particular about horror films, and in general it’s a genre I avoid. Excessive gore and jump scares do nothing for me, and it’s rare that I find any depth or poignancy in scary movies. When I do find myself enjoying one, it’s typically either because of its atmospheric qualities, or its clever plotting. When the teenagers decide to split up and see if the chainsaw-wielding hockey player will forget about them, I lose interest. I’ve now watched It Follows twice, and both times found it mesmerizing. The vaguely ‘70s-ness of the film sets a mood, and the unseen yet creepy adversary is quite terrifying. This is an intelligent, scary film that doesn’t treat its audience like imbeciles, and I’m all for it.

86. The Green Knight
David Lowery (2021)

This was a stunning film to see in a theater. The bleakness of the landscapes and the chill of the winter seemed to ooze from the screen, and every footfall echoed throughout the auditorium. The Green Knight is fearsome, Sir Gawain is chivalrous, if imperfect, and the film slowly builds to what can only be described as a perfect final moment. In a perfect world, this would have been given the Best Picture Oscar for 2021, while in our cruel world it wasn’t even nominated. What won that year? Who knows? Who cares?

85. Tangerine
Sean Baker (2015)

This film isn’t for everyone, but it’s become one of my favorite Christmas movies of all time. Were it released today there would no doubt be an uproar, but it was made in simpler times, when men who dressed as women were called trannies, and no one was advocating for chopping the wieners off of 6-year-olds. It’s hard to believe how much society has changed since then, nearly certainly for the worse. In any event, this is a charming, if raunchy, little Christmas tale featuring pimps, hoes, johns, and all the other traditional Yuletide characters. It comes from Sean Baker, the guy who won best director for Anora at this year’s Oscars, back when he was still shooting movies on his iPhone.

84. The Dark Knight
Christopher Nolan (2008)

Boy, do some people loooove this movie. I like it. It’s good. I think it falls apart in its final act, with a very forced conclusion that sort of undermines the entire film, but Heath Ledger is so darn good as the Joker that it snuck into my top 100.

83. Unfinished Business
Ken Scott (2015)

Vastly underrated and riotously funny, Unfinished Business is a film I can watch over and over. Vince Vaughn’s Dan Trunkman has quit his job after a pay dispute, and impulsively decided to start his own company. A co-worker, Tim, who has been fired for being too old comes along with him, along with a kid named Mike, who happened to be in the office for an interview at the time Trunkman quit, and was inspired to join him. From there, it’s one long, funny struggle as Trunkman tries to save his company, and his two employees’ jobs, against an ever-growing list of obstacles.

82. Kamikaze Girls
Tetsuya Nakashima (2004)

I’ve watched this film many times, and it never gets old. It’s a story of an unlikely friendship between a girl who lives her life as she’s in a Rococo painting and another who is a burgeoning gangster, and runs with a gang of motor scooter riding bad girls. It’s both comedic and tender, as it examines each of their attempts to form a friendship after spending most of their lives relying only on themselves.

81. Let Me In
Matt Reeves (2010)

I know I’ll hear it from the “the foreign original is always better!!” crowd, but this is a case where the American remake is clearly superior. I definitely enjoyed Let the Right One In, but it doesn’t have quite the polish of Reeves’ version, and ultimately, it feels like just another vampire film, albeit a slightly amateurish one, which I mean in a good way. Let Me In perfects what Tomas Alfredson only managed to touch upon in the Swedish original, and a precocious Chloë Grace Moretz is the perfect choice for the mysterious Abby.

80. Unbreakable
M. Night Shyamalan (2000)

Ah, to go back to when M. Night Shyamalan could do no wrong. Unbreakable is the second in the streak of four excellent films that kicked off his career, and no one could have seen the precipitous drop in quality that his films would take. Shyamalan was able to follow up his masterful debut with a film that was almost as good, giving us a superhero film unlike any other. Perfectly paced, dryly funny, and with an unexpected twist, this is everything Shyamalan used to be known for, and the sort of movie I wish he could make again.

79. Pirates of the Caribbean: The Curse of the Black Pearl
Gore Verbinski (2003)

When they say they don’t make ‘em like they used to, this is the sort of film they mean. It’s hilarious, it’s thrilling, it’s full of beautiful faces and frightening villains, and it has a plot full of enough twists and surprises to keep the viewer invested until the final scene. It’s perhaps the best pirate film ever made, and Johnny Depp’s finest role. I really do wish they still made ‘em like this. Unfortunately, all four sequels have been duds.

78. The Patriot
Roland Emmerich (2000)

There’s Heath Ledger again, this time holding his own against Mel Gibson in yet another of the sort of blockbusters that are no longer made. This is starting to feel like a recurring theme. It’s no wonder cinemas are struggling lately. Hollywood has stopped making the kinds of movies that used to fill seats. We used to get multiple films like this every summer, now we’re lucky to get one every decade. Why?

77. The Birthday
Eugenio Mira (2004)

This is a very slow burn, that builds to a tipping point, and then proceeds to tip over just as slowly as it built its way there. Along the way, it lurches and veers, but it never makes a misstep. Corey Feldman is better here than in any other role I’ve seen him play. He stars as a somewhat bumbling introvert, but never once overdoes it. He never takes a pratfall, or behaves stupidly. Everything he says and does makes sense within the context of the moment, and though he's meek, he's never weak. The best way to describe this film might be to say its like a David Lynch movie, if David Lynch was trying to make something coherently scripted. More people need to see this movie.

76. Guardians of the Galaxy
James Gunn (2014)

Back when Marvel movies were can’t miss events, it was announced that the upcoming film would feature a group of heroes that even I, an avid comic reader as a child, had barely heard of, and one I knew nothing about. A talking raccoon? A walking tree? It seemed certain that the franchise was poised to jump the proverbial shark. And then they released one of the funniest, most heart-warming, and exciting superhero films of all time, a film that marked the beginning of the greatest era of the MCU, rather than the end. Sadly, we’re well past that era now. One hopes the upcoming Fantastic Four film will right the ship, but it’s highly unlikely we’ll ever see a return to the glorious days of Starlord in a dance-off with Ronin with the fate of the universe hanging in the balance. Once, we were Groot.

75. Mission: Impossible III
J.J. Abrams (2006)

This the one truly great film in an otherwise forgettable franchise that has been dragged on well past its expiration date. J.J. Abrams created a truly thrilling, scary epic, and not only gave us the best version of Ethan Hunt we’ve seen, but one of cinemas most fearsome villains of all time in Philip Seymour Hoffman's Owen Davian. It’s a wonder they even made a third film after the travesty of the second one, but thankfully they did. We didn’t need five more after this one, but that’s Hollywood for you.

74. Anything Else
Woody Allen (2003)

There was a time when you could look forward to Woody Allen releasing a movie every year, and just about every one of them was great. He had an incredible run of films. In the 35 years between 1969’s Take the Money and Run and Anything Else he released 32 films, many of which are masterpieces, and even the worst of which are still highly enjoyable movies. After this film, his work became somewhat uneven. I've enjoyed some of what followed, but this was his last truly great film, and the last one that felt like what we all think of when we think of “a Woody Allen movie.”

73. Drag Me to Hell
Sam Raimi (2009)

This is perhaps the perfect horror film. It’s smart, it’s scary, it’s funny, and most of all it has a momentum that carries through to its final, horrific conclusion. It’s tightly plotted, and aside from its supernatural elements, it all makes sense. Sam Raimi is maybe the most underrated director of all time, who is capable of turning out a masterpiece in nearly any genre. He’s most known for his horror films, but he’s also made an all-time classic Western, several beloved superhero films, a sports drama, a heist film, and just about everything else you can imagine. He’s about as close as we have to Howard Hawks working today.

72. Team America: World Police
Trey Parker (2004)

The world had never seen anything like this when it came out, and maybe hasn’t since. Irreverent, raunchy, and side-splittingly funny, it went where no movie, let alone puppet show, had ever dared tread. From the opening fake-out of the street puppeteer to the love-making marionettes, this film leaves no taboo unturned, and it never lets its foot off the gas. Did I mention it’s a musical?

71. Captain America: The Winter Soldier
Anthony and Joseph Russo (2014)

Another MCU film that makes the grade, The Winter Soldier is closer to an espionage film than it is to a superhero film. Granted, it has the derring-do and larger-than-life set pieces that one demands of the genre, but in its overall execution it’s closer to Three Days of the Condor than it is to The Avengers. If you can manage to go into it without any spoilers you will be rewarded with some very dramatic moments, but even if you know what’s coming, it’s still a treat to watch the film get there.

70. Whiplash
Damien Chazelle (2014)

Sometimes you need tough love to become the best at something, especially if that thing is being a jazz drummer. As Terence Fletcher, J.K. Simmons gives a performance that makes his J. Jonah Jameson seem like Mahatma Gandhi.

69. Baby Driver
Edgar Wright (2017)

Here we have the playlist as a movie, but with impeccable dialogue, terrific acting, and a romance you can’t help but root for. Baby Driver is stylish without being flashy. Edgar Wright knew exactly where the line was and never crossed it. I have a bit of a personal attachment to the film, because the playlist, which is almost a character in the film, so closely mirrors what I listen to that I sometimes wonder if Wright hacked my iTunes to make his movie. But even if you’re not into the strange old songs that Baby plays, the movie should still be a whimsical delight for you just as it is for me.

68. Star Wars: The Force Awakens
J.J. Abrams (2015)

It can be easy to forget how great this film is after the two horrible sequels it spawned, but in and of itself this is as good as it gets after the original two Star Wars films. I rate it slightly above Return of the Jedi, but even if you are married to the original three, you can’t dismiss this film. It’s epic in a way the originals could never be, as it benefits from modern production values and pacing. Eschewing CGI for practical effects in many places, J.J. Abrams crafted a truly worthy followup to the original trilogy, full of action and emotion. When Luke Skywalker’s lightsaber zips past the expectant hand of Kylo Ren, and plants itself firmly in Rey’s hand, I felt my eyes misting up, no lie. Yes, I cried at a Star Wars movie. (I also cry when Leia hears Luke calling to her at the end of Empire, so there.) Nothing is better than when a film earns the emotions it’s trying to conjure, and after seeing Rey dismissed, forgotten, and insulted, and watched her struggle and fail through the course of the film, her grasping that lightsaber felt like a moment of triumph not just for her, but for the entire audience that had endured her hero’s journey. I’ll never forget the audible gasp at that scene from nearly everyone in the packed theater on opening night, a gasp repeated on each subsequent viewing during its run. What a movie.

67. The Hangover
Todd Phillips (2009)

The Hangover is a superbly written comedy that came out of left field in 2009, and delivered nothing but laughs for its entire runtime. It spawned some mediocre sequels, but the original is uproariously funny. It never shifts gears, and doesn’t try to be anything that it isn’t. It’s vulgar comedy from start to end, and it doesn’t need to be any more than that.

66. Uncut Gems
Benny and Josh Safdie (2019)

Who ever thought that Adam Sandler had it in him to star in a good movie? I know he tried in Punch Drunk Love, but that was more of a meandering arthouse mess than a coherent, good film, and you could see that he was trying too hard to be a Serious Actor. Besides that he’d only been in lowbrow comedies that are barely watchable, and he was perhaps the actor you least expected to make a good film. And then, out of nowhere, he delivered this performance. Now he’s back to the dreck, but you have to wonder if he’s got another one in him.

65. Lost in Translation
Sofia Coppola (2003)

This seems to be a love it or hate it movie, and I’m firmly in the love it camp. Bill Murray has never been more drolly funny than he is here, and you want nothing more than to hang out with him and Scarlett Johansson as they explore Tokyo, and develop their unlikely friendship. It’s sweet and it’s sad, and it’s never not entertaining. Plus, it makes you ponder your own life, and it’s great when a film can make you do that. Mostly though, it’s just really, really funny.

64. Dredd
Pete Travis (2012)

I didn’t expect much when I went to see this movie. I don’t even recall why I saw it. I think it was one of those “let’s go see a movie” nights where you watch whatever starts next, and this is what happened to be starting next. I’d seen the lousy Stallone version of the character, which lowered my expectations even further, so imagine my surprise when I saw the completely awesome, non-stop thrill ride that is Dredd. It’s so simple. Dredd and his partner are locked in a building, and have to navigate from one end to the other to get out, overmatched by enemies every step of the way. That doesn’t seem like enough, but it’s all you need. They should show this in film studies classes to teach how to build tension and how to keep a plot tightly focused on what matters most in a film.

63. Tropic Thunder
Ben Stiller (2012)

Robert Downey Jr. in blackface? Check. Jack Black Jack Blacking? Check. Tom Cruise as an overweight foul-mouthed balding film producer dancing to Apple Bottom Jeans for Matthew McConaughey and Bill Hader? Check. Ben Stiller going full retard? Check. Nick Nolte is in this movie? Check. It’s literally got it all.

62. Nebraska
Alexander Payne (2013)

I love films that tell a good story, and introduce you to, and expand upon, great characters, and that’s exactly what this is. Shooting it in black and white only serves to enhance that, and gives an almost poetic resonance to the scenery. This may not be for everyone, but this is right up my alley. Paradoxically, though it ranks lower than another film from 2013, this is the film I’d have awarded that year’s Best Picture Oscar to, if I ran the zoo. Don’t ask me to explain. Like I said, I’m lousy at ranking things.

61. The Fellowship of the Ring
Peter Jackson (2001)

Unpopular opinion: the Lord of the Rings films got progressively worse, and The Return of the King is a bloated mess. I know, I know, save your voice. I’ve heard it all before. I thought the initial film was revelatory, with its expansive shots and perfect soundtrack, and the way it brought Tolkien’s world to life was nothing short of astounding. The second film was a dark slog, mired down too much in the siege. While the last film had some glorious moments, but wasted far too much time at the end that should have been devoted to aspects of the story that were omitted in lieu of hobbits bouncing on beds. But this one, this film, this hits every mark. This one is excellent.

60. Young Adult
Jason Reitman (2011)

I know this won’t make too many people’s best-of lists, but I adore this film. It’s not easy to watch at times, as Mavis Gary, played by Charlize Theron, is not always a likable protagonist. In truth, she’s the sort of person most of us knew, and hated, when we were young. But she’s all grown up now. She’s a young adult. Also,she writes young adult fiction. She’s returned to her small Minnesota hometown to attempt to break up the marriage of her high school sweetheart, who wants no part in her plan. Still, she persists, with humorous, and often awkward, consequences. Patton Oswalt plays Matt, a former classmate she barely remembers, who endured a beating during high school that left him disabled, and he almost steals the movie. He attempts to act as Mavis’ conscience, though he is not very successful at it. If that sounds dark, it is, sort of, but mostly this is a funny movie with a lot of rewatch value.

59. The Interview
Seth Rogen and Evan Goldberg (2014)

Has it really been 11 years since Hollywood released a great comedy? Sadly, yes it has. We used to get a dozen or more per year. Hell, in 1994 Jim Carrey alone starred in three comedies that are now beloved classics, but since The Interview I can’t think of a single truly great comedy. About the only one that’s even close is Game Night, and even that came out 7 years ago. Nonetheless, while it may be the last one, it is indeed a great comedy, possibly the funniest movie of the 21st century so far. When James Franco’s Dave Skylark finally gets around to interviewing Kim Jong Un, the result is unbelievably funny, as is just about every gag and line in this movie. I truly hope Hollywood gets back to making this sort of comedy again, and soon.

58. Monsters, Inc.
Pete Docter (2001)

I’ve already lamented the demise of Pixar, and I won’t repeat myself other than to say that I wish they still made them like this. If there’s a funnier cartoon character than Mike Wazowski, I need to know about him right away.

57. Faat Kiné
Ousmane Sembène (2000)

You must think I’m some deeply educated cinephile to pull a Senegalese movie out of my hat, but it’s not like that. I happened upon this film quite by chance, when I checked out a festival of films from Senegal, and this is the one that stood out to me. It’s an entertaining and powerful film, and it offers a street-level view into life in Senegal, as well as to the shared human experience of romance and marriage that exists everywhere there are people. Fun fact: once I almost got on a plane to Senegal, mostly because I liked this movie so much, but a plane headed to Morocco was leaving sooner so I took that one instead.

56. Requiem for a Dream
Darren Aronofsky (2000)

It’s bleak. It’s dark. It’s awful. It’s what I assume to be the most realistic depiction of heroin abuse ever put onto film. I prefer Trainspotting as a film, by a wide margin, but this feels a lot more real. Granted, I’ve never used heroin, so who am I to say, but everything about this film, from its lighting to its pacing to its terribly unfortunate ending strikes me as the reality of substance abuse.

55. American Sniper
Clint Eastwood (2014)

Another Clint Eastwood film makes the list, this time a biopic featuring Bradley Cooper as Chris Kyle, the deadliest marksman in American history. It details his life before, during, and after his four tours of duty in the Iraq War, and covers some pretty dark territory. Eastwood knows how to shoot a drama like this better than almost anyone, and he’s definitely up to the task here.

54. Oldboy
Chan-wook Park (2003)

Yet another film I discovered by walking into a theater to see whatever was playing next, Oldboy had a limited release in American theaters in March, 2005, and I was lucky that the theater down the street my apartment was showing it. I had no idea what to expect, and while I won’t spoil the ending, I have to admit that I saw it coming almost from the get-go. Even so, that didn’t detract one bit from the power of the film, and I was in awe the entire way. I haven’t seen Spike Lee’s remake, but I’ve heard it doesn’t measure up to this Korean original. If you can handle violence and depravity on film, this is well worth watching. There’s a scene in a hallway that must be seen to be believed.

53. Dunkirk
Christopher Nolan (2017)

I love the way Nolan manages the passage of time in this film. He interweaves three disparate stories, one that takes place over the course of a week, on land, one that takes places during 24 hours at sea, and one that relates an hour of action in the air. He layers them so that the week, day, and hour, are overlapped, and we see all three unfold atop one another during the span of the film. It’s brilliant, really, and something I’ve never seen done before. Besides that clever way of interspersing multiple stories, the film itself is exciting, a retelling of the evacuation of Dunkirk, known historically as the Miracle of Dunkirk, during the second World War. If you told me you thought this was Nolan’s best work, I wouldn’t argue with you, at least not too much.

52. Godzilla
Gareth Edwards (2014)

Yes, a Godzilla film has made the cut. But what a film. This is not your grandfather’s Godzilla, as the big beast takes a backseat to some very well-crafted human stories, and that’s what won me over. The incredible scenes of the monsters were the icing on the cake. I grew up watching all those old Godzilla films, with the guys in foam rubber suits splashing around in outsized bathtubs, so to see my childhood favorite looking so real was a treat. I also loved how the Godzilla reveal kept being delayed. I saw this opening night in a packed theater, and the anticipation each time it seemed we were about to see him was palpable. We see him fighting a M.U.T.O. in the background, on a TV, but only briefly. Later, he’s about to appear, just as the doors close. So many close calls! The build-up was extraordinary, so when he finally did appear in all his glory, the audience went absolutely bananas. And then he breathed fire, and I swear I thought the roof was going to come off the building. Say what you will, this is pure cinema.

51. Napoleon Dynamite
Jared Hess (2004)

The local arthouse theater ran the trailer for this before seemingly every film I saw there in the months leading up to Napoleon Dynamite’s release, and from the first time I saw that trailer, and heard Napoleon declare “it’s my ride” I was sold. I was in the house on opening night, along with a decent-sized audience, to witness a film unlike any I’ve seen before or since. I once read that in its early days, Netflix offered a reward to anyone who could create an algorithm that would predict whether or not a viewer would love or hate this film, and that rings true. People I’d expect to adore this film end up despising it, while others I’d never suggest it to out of certainty they will hate it surprise me when they say it’s among their favorite films. You never can tell. Me? I love it.

50. Brick
Rian Johnson (2005)

Brick takes the classic hard-boiled film noir detective and reimagines him as a high school student. All of the typical hangups and emotions that plague the typical teenager are writ larger than life as the overwrought adult world of noir is superimposed on the high school dynamic. Classmates can be kingpins, bullies their enforcers. Oh, and there is a murder.

49. Idiocracy
Mike Judge (2006)

I still remember my first thought as I left the theater after seeing this in 2006. “It won’t take us 500 years to get there.” I’m even more confident in the truth of that statement today than I was then. How long will it be before the genre on Idiocracy is quietly changed from comedy to documentary?

48. The Wrestler
Darren Aronofsky (2008)

For someone who didn’t see Mickey Rourke during his leading man era in the 1980s, it’s hard to imagine the misshapen brute who plays the titular wrestler could ever have been cast as someone unironically named Johnny Handsome, but here we are. Rourke, the epitome of cool in The Pope of Greenwich Village accidentally boxed and botox-ed himself into shape for this comeback role. He’d go on to steal the show in the vastly underrated Iron Man 2, but it all (re)starts here.

47. Superbad
Greg Mottolo (2007)

It seems like every generation gets its own high school coming of age movie, and this is the Millennial take on the genre. At the time it felt like an update of the Gen-X experience, but now this feels like an ancient relic, and something Gen-Z and beyond will find incomprehensible. Yes, believe it or not, high school students used to drink, throw parties, dance, and have sex with one another. One wonders what Gen-Z’s high school movie will look like. I imagine we'll find out soon.

46. In Bruges
Martin McDonagh (2008)

A smartly written romp through one of Europe’s most beautiful cities, In Bruges is an intellectual buddy comedy where two utterly mismatched criminals try, and fail, to lay low for awhile after a caper gone wrong. If you’re a fan of dialogue-driven comedy, you’ll appreciate this film.

45. Sideways
Alexander Payne (2004)

Wryly funny, heartbreaking, and cringe-inducing all at once, Sideways takes all of the buddy road comedy tropes and turns them on their head. Or perhaps, on their side? It’s the story of a mismatched pair of friends out for one last hurrah, each seemingly trying to out-asshole the other.

44. Scott Pilgrim vs. the World
Edgar Wright (2010)

A bizarre intersection of the science fiction, comedy, superhero, and teen angst genres, there are few, if any, films like this one. It’s certainly clear by now that my taste skews towards films with witty, intellectual dialogue, which is exactly what makes this film so good. Its a nonstop barrage of jokes, but never once does the film go lowbrow or rely on easy laughs. Scott Pilgrim is the true everyman. He’s conflicted. He knows the person he wants to be, but can’t always do what he knows to be the right thing.

43. The Baxter
Michael Showalter (2005)

The Baxter is the movie that imagines Ralph Bellamy actually getting the girl in the end, instead of Cary Grant. It’s the average schmoe finally holding on to his girl when the hero swoops in to steal her away. Or is it? Will he be left at the altar after all?

42. Moneyball
Bennett Miller (2011)

Moneyball is a movie you can watch over and over again and never tired of it, entirely because of the brilliantly crafted dialogue. Shakespeare couldn’t improve on this script, and the quiet majesty of our national pastime provides the perfect backdrop for the drama that ensues.

41. Gangster Squad
Ruben Fleischer (2013)

1949 Los Angeles is as much a character in this film as any member of the Gangster Squad, her neon lights and lavish supper clubs come back to life, if only for the runtime of a movie. Loosely based on true events, this film is filled with wonderful moments between interesting characters, portrayed by excellent actors. Did I mention all the neon?

40. The Cabin in the Woods
Drew Goddard (2011)

This is almost certainly the cleverest horror film ever filmed. Every trope of every teen horror film or slasher movie is examined and metatextualized. It’s intelligent, hilarious, and scary, and utterly unpredictable. Go into it cold. You only get one first watch of The Cabin in the Woods in your life, so don’t ruin it with spoilers!

39. The Batman
Matt Reeves (2011)

Many people consider The Dark Knight to be the best Batman movie. I think it’s the best Hollywood Batman movie. It hits all the right notes, and aims low to find its audience. Though I was skeptical of The Batman when it came out, I saw it twice in the cinema, and was enthralled both times. Pattinson’s Bruce Wayne comes off exactly like you’d imagine someone crazy enough to dress like a bat and fight crime would be. Unlike Bale’s polished millionaire, who seems out of place in the bat suit, Pattinson makes sense. His Batman is a detective first, and a fighter second, and Dano’s Riddler gives Ledger a run or the money in the villain department. Batman was meant to be a dark, angsty, crazed character, and I can’t imagine any future version surpassing this one.

38. Hacksaw Ridge
Mel Gibson (2016)

Sometimes true stories can be as, or even more, uplifting than anything fictional. Such is the case of Desmond Doss, a US Army medic who served in the Pacific theater and became the first conscientious objector to receive the Medal of Honor. And say what you will about Mel Gibson, he knows how to depict the horrors of battle on a silver screen.

37. Bone Tomahawk
S. Craig Zahler (2015)

No genre has disappeared from cinemas more dramatically than the Western. Hollywood used to churn out dozens, probably hundreds, of oaters every year. Now it seems years go by without a single one appearing in a theater near me. Even rarer? An excellent Western, which is exactly what Bone Tomahawk is. It has a few moments of extreme violence that almost veer it into horror territory, but this is a classic and compelling cowboys vs. Indians story like you seldom see anymore.

36. Spirited Away
Hayao Miyazaki (2001)

This is a beautiful cartoon that has equal appeal for adults and children. Chihiro interacts with ghosts, dragons, and mythical beasts in an attempt to save her parents, and ultimately saves the day through selflessness and kindness. Kids will enjoy the exciting and funny scenes, and parents the message that if you live with honor and integrity you can overcome whatever life throws at you.

35. Old School
Todd Phillips (2003)

What is the funniest pure comedy of the 21st century? Old School, that’s what. Expertly toeing the line between zany and heartfelt, this film always manages to keep the audience rooting, and feeling, for Mitch. Will Ferrell, always best in short doses, is utilized perfectly here, and his keg scene is among the all-time great classic bits. Vince Vaughn rounds out the trio, and together they capture lightning in a bottle.

34. La La Land
Damien Chazelle (2016)

On the surface, this movie is a joy to watch. It’s bright colors, beautiful faces, and wonderful music. If you, like me, are from Los Angeles, it’s more than a little bittersweet. Retro Dairy, The Rialto, Magnolia Theatre, and other long gone relics of L.A.’s better days appear onscreen, a reminder of how the city discards its history without a care. This is even referenced in the film, when Ryan Gosling’s Sebastian declares about the city, “They worship everything and they value nothing.” Nonetheless, this is a touching portrait of a city of dreams that examines what happens when you follow one of those dreams at the expense of another, and that hindsight is always 20/20.

33. The Avengers
Joss Whedon (2012)

Some may take issue with yet another superhero film making this list, but like it or not, the better part of the 21st century has been the era of the superhero film. Hollywood has been putting all its chips, and biggest stars, into the comic book pot, and there have been more than a few fantastic films as a result. None are better in my book than The Avengers, the film in with Marvel brought together the heroes whose stories they’d been telling into one larger-than-life ensemble piece. This could have gone so wrong (see the Justice League movie) but in the hands of Joss Whedon, it’s the perfect superhero movie. It looks beautiful, it’s paced perfectly, and it is satisfying on every imaginable level.

32. The Lives of Others
Florian Henckel von Donnersmarck (2006)

Here’s a film that pulls you in, and keeps you on the edge of your seat from start to finish. You truly care about the lives of the others in question. This is a fantastic modern take on the classic Cold War spy thriller, and a film that stand up to repeat viewing.

31. Signs
M. Night Shyamalan (2002)

This is one of my favorite alien invasion movies of all time, primarily because of how small a role the aliens play. Instead, they’re more a Maguffin to tell the story of a priest who has lost his faith, and how he goes about rediscovering it. Meanwhile, though the aliens barely show themselves, Shyamalan offers a masterclass in building suspense and creates a film worthy of the master himself, Hitchcock. I know his career took a nosedive not long after this, but Signs is an absolute, stone cold masterpiece of suspense.

30. My Sassy Girl
Jae-yong Kwak (2001)

Little-known stateside, this Korean film is a delight, and a crowdpleaser. If you can convince your friends to give a foreign film a chance, there’s little doubt in my mind they will thank you when this film ends. In the original title, the sassy girl is yeopgi, which I’ve heard translated as someone who seeks interesting or strange experiences, and sometimes simply as “spicy.” I’ve also seen this film titled “That Bizarre Girl.” All of those terms sum up the girl in question, in what is said to be a true story that began its life as a series of blog posts that were later adapted into this film.

29. No Country for Old Men
Joel and Ethan Coen (2007)

I think this movie would have ranked even higher on my list had I not recently read the book this film was based on, and then rewatched the film immediately after. Suddenly the film felt herky jerky, and lacking in so many ways. I know that the book is always better than the movie, unless Elmore Leonard wrote it, but still— there was such greater insight into the characters in the book, that I can’t help but, probably unfairly, knock this down a few places from where it otherwise may have landed.

28. Parasite
Joon Ho Bong (2019)

Here’s the picture that topped the New York Times’ list. It’s certainly a good movie, a great one, even, but the best of the century so far?? Far from it, in my opinion. I’m a huge fan of Korean cinema, so perhaps since this is for many people the only Korean film they’ve ever seen it resonates more deeply, but for whatever reason, I don’t think this is the absolute best of the best as many clearly do. It sure is good, though. It is definitely a clever, and balanced, critique of class differences, and a funny, engaging film from start to end.

27. Shadow of the Vampire
E. Elias Merhige (2000)

What a great conceit: imagine if F.W. Murnau had cast an actual vampire in the role of Nosferatu when he shot his famous film. I’m a massive fan of the original film, and Murnau’s work in general, so this film appeals to me on multiple levels, but even someone without an appreciation for German expressionist cinema should find delight in this film. After all, how many vampire quote Tennyson?

26. Black Swan
Darren Aronofsky (2010)

A psychological thrill ride, and an erotic masterpiece, Black Swan is and unrelenting movie. Strap in for a ride that never lets up for an instant. If you do watch, or rewatch, this movie, pay attention for clues to prove or disprove my pet theory, which I’ve nearly never heard addressed elsewhere: I think the mom is in her mind. Discuss.

25. Midsommar
Ari Aster (2019)

Imagine the 1973 film The Wicker Man, except if it were a good movie, and you have the seed that will grow into Midsommar, Ari Aster’s masterpiece of slow burning horror and suspense. All sorts of mysterious, seemingly inexplicable moments all come together at the end, in one monumentally powerful finale that will stay with you for a long, long time.

24. The Nice Guys
Shane Black (2016)

After an incredible debut film, which you will encounter closer to the top of this list, Shane Black had a couple miscues before knocking it out of the park again with The Nice Guys. 1970s Los Angeles is the scene for this hard-boiled, noire-esque comedic drama of a buddy movie that keeps me both engrossed and in stitches every time I watch.

23. Mad Max: Fury Road
George Miller (2015)

You wouldn’t think a film that is basically a long car chase, followed by a second long car chase, could be so good, but somehow, George Miller pulls it off. The usage of practical effects rather than CGI for many of the stunts is noticeable, or rather, you don’t notice the lack of reality that is always in the back of your mind when watching CGI. This looks like exactly what it is: actual humans doing actually crazy stunts. Seeing this projected in 70mm was an experience I will remember, and treasure, for the rest of my life.

22. The Death of Stalin
Armando Iannucci (2017)

A bit of an under-the-radar picture, this is a remarkably funny and unceasingly interesting movie that constantly ups the ante, as it tells the more or less entirely true story of Stalin’s death. It offers a glimpse behind the Iron Curtain, and allows Steve Buscemi to showcase a completely different side of his acting chops. Here he plays Nikita Khrushchev, who went from being Stalin’s court jester, for lack of a better term, to his ruthless heir. See how it all unfolded.

21. Once Upon a Time... In Hollywood
Quentin Tarantino (2019)

Apart from delivering a densely plotted, deep character study of an actor receiving accolades for basically pretending to be his best friend, who languishes in poverty, kudos to Quentin Tarantino for casting a veritable who’s who of nobodies who were about to become somebodies, with Austin Butler, Sydney Sweeney, Mikey Madison, Dakota Fanning, Maya Hawke, and others all popping up in this film. I have far more to say about, which you can read here if you wish, but suffice to say that this is a masterpiece.

20. Gladiator
Ridley Scott (2000)

If this film has any weakness, it’s that the very best scene comes too early in the film. For my money, the moment when Maximus turns and reveals his identity to Commodus is one of the two or three greatest moments in the entire history of cinema, so the rest of the film feels like a bit of a comedown after that highest of highs. It’s a minor gripe, to be sure, as the entire film packs a huge emotional punch, peppered with some timely bits of dry wit.

19. The Rules of Attraction
Roger Avary (2002)

Despite co-writing Pulp Fiction, one of perhaps 3 or 4 films that can be said to have altered cinema forever, Roger Avary has had a very quiet career. Nonetheless, he has this one true masterpiece to his credit. At times it’s shocking, often it’s hilarious, and cinematically it is sometimes experimental, as it runs whole scenes backwards to arrive at points of deviation in the story. It may also be incomprehensible to the youth of today, as grounded as it is in Gen-X ideals and morals. All I can say is trust me, this is how we were then, and we aren’t ashamed of it now. At least, not as ashamed as some may say we should be. Maybe all I needed to say is that this film is based on a novel by Bret Easton Ellis? Now it all makes sense.

18. The Artist
Michel Hazanavicius (2011)

Granted, I’m a huge fan of silent films, so I may be biased, but I’m not alone in loving this film. It won the Oscar for Best Picture after all, and in all honesty, it’s a movie for anyone who loves movie, be they silents or talkies. It’s good clean fun from start to finish, and it has a great dog. Could you ask for more?

17. O Brother, Where Art Thou?
Joel and Ethan Coen (2000)

I’m a huge fan of the Coen Brothers, and my favorite director of all time is Preston Sturges, so when heard the Coens were making a film called O Brother, Where Art Thou?, I was sold. The fact that it turned out to be such a lovely film was mere icing on the cake. The soundtrack, which unexpectedly rocketed up the pop charts, is made up of many great folk and mountain music classics, and the film is a comedic romp in the fashion of all the Coen Brothers best films. It’s a loose— very loose— adaptation of The Odyssey, that follows the journey of three escapees from a chain gang, and the ob-stackles they face along the way.

16. The Royal Tenenbaums
Wes Anderson (2001)

Wes Anderson has been the most consistent director of the modern era. He’s made a dozen pictures, ten of which are excellent movies. The difference in quality between his best movie and his 10th best is small. He definitely has a style all his own, and an aesthetic that is recognizable, but his films are all quite different in the emotions they conjure in their audience. The Royal Tenenbaums is a wonderful look at the family of gifted children who are all grown up, and finally facing the childhood experiences that shaped them as they attempt to reconcile with their estranged father.

15. There Will Be Blood
Paul Thomas Anderson (2007)

A long, dark look at the early days of the oil industry, told through the story of one oilman and his battle against, well, everyone. This is as much about the dangers of unchecked competitiveness as it is about oil. Paul Dano, young and relatively unproven at this stage in his career, holds his own against a masterful performance by Daniel Day-Lewis.

14. Memento
Christopher Nolan (2000)

It’s not often a director comes up with a novel way to tell a story, but Christopher Nolan found a way to tell a story backwards while keeping it completely coherent. Memento is a taut, tense and ultimately heartbreaking story that will please a mainstream audience, despite its auteur leanings.

13. Babylon
Damien Chazelle (2022)

Over the top doesn’t begin to describe the level of excess on display in this film, which begins with an elephant taking a dump on someone before escalating into a party worthy of Jay Gatsby. Amidst the decadent celebrations we get a glimpse into the transitional era when silents gave way to talkies. Brad Pitt’s Jack Conrad seems to be based on John Gilbert, with a little bit of Valentino and Fairbanks thrown in, while Margot Robbie as Nellie LaRoy takes inspiration from Clara Bow. Don’t be fooled by the mayhem, there are some deep moments here, and the entire film is a love letter to the magic of the cinema.

12. Zodiac
David Fincher (2007)

As a recreation and examination of the Zodiac murders, this film is good enough to make this list. The exploration of the characters involved in the story is what elevates it to 12th place. Gyllenhaal, Downey, and Ruffalo each bring their A-game, and the result is something gripping and re-watchable, a rarity in the true crime genre.

11. Amelie
Jean-Pierre Jeunet and Marc Caro (2001)

There are many thought-provoking films, but few truly life-changing films. Amelie falls squarely into that second camp, offering its viewer permission to live a life of selfless whimsy, a choice many viewers at the time adopted. It escaped mainstream notice, but to the ardent cohort who watched this film, Amelie became something of a superhero, a fictional character to aspire to being, and who inspires a radical rethinking of how one spends one’s days.

10. In the Mood for Love
Wong Kar-Wai (2000)

If you complain that nothing happens in this movie, you won’t be wrong. It has nearly no plot to speak of, yet it possesses a power unlike few other films. I know of no other movie that expresses the feeling of longing so completely, as the film immerses the viewer into the quiet stoicism of the leads. We never even see their spouses, nor do we need to see them. This is pure emotion in cinematic form.

9. Interstellar
Christopher Nolan (2014)

Nolan’s at it again, this time tackling the sci-fi genre. As original as ever, he treats his material like high art, and brings a new take to a tired genre. The science is smart, the action tense, and the emotional stakes are high. This film works on every level.

8. Inglourious Basterds
Quentin Tarantino (2009)

“I think this just might be my masterpiece.” Those are the words Brad Pitt speaks to close this film, but they may also sum up Tarantino’s feelings about his 7th film (6 if you count both Kill Bills as one film, as he does). It’s hard to argue with him, though I’ll still put Pulp Fiction and Jackie Brown ahead of this one. That isn’t criticism, as this is a fantastic film. It’s hilarious, but also thrilling. This is the film that introduced the world to Christoph Waltz, who burst onto the scene here, clearly destined for stardom. This film also has perhaps the greatest opening scene in the history of movies.

7. The Darjeeling Limited
Wes Anderson (2007)

Often overlooked in Wes Anderon’s filmography, The Darjeeling Limited is his most mature and complete film to date. It has the pretty colors and interesting camerawork that one expects from Anderson, but it also has three complex characters dealing with the loss of their father, the disappearance of their mother, and the after-effects of their upbringing on where they are now. If this sounds like a more nuanced and mature take on the themes of The Royal Tenenbaums, that’s because it is. Anderson, a little bit older and wiser, revisits the same well, and this time draws up his masterpiece.

6. The Departed
Martin Scorsese (2006)

Scorsese has been so good, and for so long, that his best film of this century would probably rank in 6th place if matched up to his entire filmography. And that isn’t an indictment of his recent work. Both Gangs of New York and The Aviator were in this top 100 list in its early incarnation, but were ultimately pushed down by other films. The Departed, on the other hand, has been bouncing around the top 10 since the beginning. Matt Damon and Mark Wahlberg give what I consider to be both of their best performances in a film to date, and DiCaprio is excellent, as always. Jack Nicholson tones down his Jack Nicholson-ness enough to ramp it up in a different sort of way, and the film throws one tense situation after another at its audience, peppered with enough curve balls and unexpected turns to keep them perpetually off balance.

5. Kiss Kiss Bang Bang
Shane Black (2005)

It’s always Christmas in a Shane Black movie, or at least it sure seems to be. Be it Christmas or Flag Day, Kiss Kiss Bang Bang is the gift that keeps on giving. Still another “what’s playing next?” discovery, this was the film that opened my eyes to Robert Downey Jr.’s superstar potential, something the rest of the world would soon catch onto, as Zodiac, Iron Man, Tropic Thunder, an Sherlock Holmes were soon to follow. Val Kilmer, too, shines, in what would be his last truly great roles. Kiss Kiss Bang Bang won’t appear atop too many people’s lists of the best films, but I firmly believe this Mike Shayne novel come to life belongs on them all.

4. Adaptation
Spike Jonze (2002)

There are movies in which the movie turns in on itself, and becomes metareferential, and then there are movies where the metareferences themselves become metareferential. And then there are Charlie Kaufman movies. And then, after that, there is the most Charlie Kaufman of Charlie Kaufman movies, Adaptation. I can’t even begin to explain how this film folds over and atop itself, inside out and then back again, foreshadowing its own foreshadows, yet somehow all the while remaining easy to follow and entertaining.

3. City of God
Kátia Lund and Fernando Meirelles (2002)

City of God is what I think nearly every movie aspires to be. It leaves its viewer breathless. It has moments of pure joy, and moments of utter terror. Li'l Zé is one of cinema’s all-time scariest villains, and he terrorizes the audience as much as he does the denizens of the film. Yet, despite the poverty and murder, there is also a joyous side to this film, and when it depicts the dancing and beach-going, and the vibe of the ‘70s in general, it’s as immersive as any film I’ve seen.

2. Mulholland Drive
David Lynch (2001)

Only David Lynch could pull off something like this. There’s the thinnest of walls between the utter masterpiece that is Mulholland Drive, and the total schlock of something like Tommy Wiseau’s The Room, and Lynch toes that line like Nik Wallenda. When the film shifts gears from dream to reality, you realize why the acting and plot were what they were, and that takes things to an entirely different level. While Mulholland Drive isn’t the indecipherable puzzle some make it out to be, there are certain things left open to interpretation that make repeat viewings, and long conversations with friends about what you’ve seen, very rewarding, which is perhaps the best thing one can say about a film. Or is it?

1. Donnie Darko
Richard Kelly (2001)

I suppose the best thing, to me, anyway, that one can say about a film is that it tells a dense and complicated story with the bare minimum of information, and provides its audience with exactly enough data to suss out every last detail and nuance. Donnie Darko is exactly such a film. Richard Kelly makes Capra seem long-winded in the way he builds a film where every second of every scene is absolutely necessary, and removing even one moment would cause the entire film to collapse. Sadly, either Kelly or the studio couldn’t see this, and a director’s cut was later released that adds myriad unnecessary exposition and entertainment. While I dislike that director’s cut, I do appreciate it for one very important reason: after watching the original cut of this film, my friend and I spent hours talking through what we’d watched, and came up with a very detailed synopsis of what we thought was exactly what had actually happened in the movie. We had no way to know if we were right, but based on the scant details provided, it felt right. The director’s cut spoon-feeds the audience every plot point in excruciating detail, often literally spelling out on the screen with titles “here is what is happening now, and why.” The only positive was that what was spelled out was exactly to the letter what my friend and I had decided we thought the film was about. Everything needed to piece it together was there in the original cut, as long as you pay attention and use your head, two things most audiences are sadly incapable of doing.