We're getting to the point on this list where I personally love every movie on here, and distinguishing between which ones I prefer to others becomes more or less random. These sorts of decisions are always in flux, and if you asked me to compile the same list 6 months or a year from now, at least some of the rankings would have changed, I'm certain. So consider this a snapshot in time more than anything else, and a convenient way for me to spread the word on 50 great movies, some of which you may not have seen, more than a definitive list of anything.
Also I sort of cheat below and include 2 films as one item in the list. I think it's fair, though, for reasons that should become clear.
30. Overnight (2003)
"Overnight" is like a morality play for our troubled times. One of the decade's most compelling and hilarious documentaries came together as a happy accident. Writer/director Troy Duffy got a shot at making his own Hollywood film after getting a script into the hands of Miramax chief Harvey Weinstein. Naturally, he brought his friends along for the ride, some of whom decided to film the entire experience. Little did they know when embarking on the indie crime thriller "The Boondock Saints" project that Duffy would proceed to burn every bridge in town, thus ruining lifelong friendships and decimating his chances of future success as a filmmaker. (10 years later, he's still working on resurrecting his prospects following the "Boondock" debacle.) The result is a brilliant, insightful and darkly comic showbiz tragedy, and also one of the most direct and essential statements about the importance of humility, and the dangers of, as Scarface might say, "getting high on your own supply," ever set to film. (Is it a coincidence that one of the directors is also named "Tony Montana"?)
29. Songs from the Second Floor (2000)"Songs in the Second Floor" is comprised of a series of amusing, precise sketches about hopeless, adrift individuals, abandoned in an urban dystopia. This visionary, harrowing collection of small, disconnected stories from Swedish director Roy Andersson, could be broken up into a series of short films and still prove enlightening, worthwhile and frequently hilarious. But taken together, they ultimately develop into a devastating statement about the panic that runs beneath the surface of most human interactions, and the paranoia of metropolitan life at the change of the millennium. The motif of feeling "stuck" by circumstances and a claustrophobic downtown environment comes up over and over again in Andersson's world, in this film and its almost equally-brilliant 2007 follow-up, "You the Living." An endless, inexplicable traffic jab snakes through the unnamed setting, characters are seen entering the disorganized tangle of train stations and airports without ever actually getting anywhere and Andersson's motionless cinematography (almost every scene is depicted from a single, fixed perspective around which the characters move) remains permanently rooted in place, unable to effect any change or move out of the increasingly disturbing, surreal locations.
28. Match Point (2005)Woody Allen revisits the themes of his 1989 masterpiece "Crimes and Misdemeanors" in this cerebral drama, his finest work of a very prolific decade. A meditation on the nature of justice, and the sociological ramifications of a guilty person evading detection, it's above all a clever, calculating, unpredictable crime thriller. Allen, who's of course best known for comedy, proves he knows how to time a sequence perfectly for maximum suspense (particularly a sequence in an armory where the anti-hero is trying to cover his misdeeds). Caddish tennis pro Chris (Jonathan Rhys Meyers) romances shy heiress Chloe (Emily Mortimer) while having it off with fiancee Nola (Scarlett Johansson) on the side. When this situation becomes untenable, rather than risking the loss of his career prospects and meal ticket, Chris resorts to some pretty shocking, unthinkable maneuvers. Allen's film looks at the role that luck plays in all of our lives - as Chris continually avoids punishment for his crimes purely by chance - but I think it makes the larger point that, regardless of how things work out, we live in a world where the moral codes exist only inside our heads. Getting away with any breach of the social contract or taboo is simply a matter of good planning and hoping the situations outside of your control happen to turn in your favor. In Allen's view, accepting this reality is both comforting and terrifying.
27. The Assassination of Jesse James by the Coward Robert Ford (2007)
The historical character of Jesse James, probably the single most famous, iconic outlaw in the history of the American West, bears pretty much zero resemblance to the man himself. Even in his own time, the public's notion of Jesse didn't really reflect the man's genuine character. Andrew Dominik's haunting, eerie and, yes, fictional look at the last few months of James' life, examines the impact fame (infamy, really) may have had on the man and his ability to relate to the world. It's that same notoriety that attracts the awkward, vaguely sinister Robert Ford (Casey Affleck) to James. He wants nothing more than to insert himself into James' circle, to assume a small portion of the man's reputation and celebrity, and when dismissed and turned away, his desperation quickly turns to rage. Andrew Dominik's Western becomes almost like a lamentation for an era we collectively dreamed about, but that never really existed. Even Roger Deakins' crisp but faded, ghostly pale cinematography drains all the color out of the Old West of popular myth, leaving only the faint, blurred outlines of gaunt, calloused pioneers we recognize from old-timey photographs.
26. Kill Bill 1 and 2 (2003-2004)Yes, yes, it's actually 2 movies, but Tarantino's "Kill Bill" series builds and unfolds like a single film, and was originally conceived that way, so I figure it counts. The logical endpoint of Tarantino's ongoing fascination with post-modernism and cult cinema, "Kill Bill" is that rare mash-up (either in film or music) that coheres into a single, unified whole. The entire idiosyncratic, unpredictable saga is, at its core, a fairly straight-forward revenge story: A former assassin in the employ of her teacher and lover, Bill (David Carradine), The Bride (Uma Thurman) ran off to lead a normal live as a Texas record store clerk and wife, only to be hunted down and (almost) exterminated by her former comrades. Now, awaking from a coma, having lost her husband and the baby she was carrying, she sets about tracking her fellow assassins down one by one, and so on and so forth. What's staggering and exciting about Tarantino's work here is about how he can hack up the narrative into achronological, fast-paced segments, reference dozens of films from a variety of eras and genres, and still produce a finished film with its own unique attitude and style. It's almost as if QT saps these old forgotten films and genres of all their energy, and infuses it all into his own work. There's a massive amount of seemingly-impossible shots, hilarious or badass bits of dialogue, dazzling action sequences and little touches throughout, enough to keep even the most observant, attentive viewer bewildered for the first few viewings.
25. George Washington (2000)David Gordon Green's lyrical, picturesque coming of age drama/thriller "George Washington" follows a group of 12-year-olds in the rural South as they face the harsh realities of life for the first time. There is a conventional plot here - about a tragic mistake made by the kids and their half-hearted attempts to cover it up - but Green's film is as much about this specific, often-overlooked place in America and the daily rhythms of life there. His North Carolina is a realistic but almost dreamlike vision, a land of sun-swept beauty but also encroaching decay. Some of the settings are stunningly beautiful, but seem to be wasting away before our eyes. Rather than a film made by an outsider attempting to explain the South and its understanding of race, Green speaks with experience, and also tremendous compassion, about the life of protagonist George (Donald Holden) and his friends, capturing their manner of speaking and adolescent impressions of the world beyond their town with patience and a practiced, archivist's ear.
24. Donnie Darko (2001)
Far more influential than it's given credit for, Richard Kelly's fusion of science-fiction, psychological horror and '80s teen comedy remains just as fresh, funny, convention-shattering and quietly terrifying today as it did 9 years ago. The movie predicted the rush of '80s nostalgia that would come to dominate pop culture in the last decade, it toyed with the same metaphysical fascination with time travel that JJ Abrams has exploited in his "Star Trek" movie and on "Lost," and it reminded us of the magnetic, movie star quality of Patrick Swayze before we all remembered how great he was. Ignore the "Director's Cut" that was eventually released for DVD; it robs the movie of its central mystery and ambiguity, trying to "explain away" the strange conundrums of the narrative, even though they are, when all is said and done, the entire purpose of the enterprise. Strange things are happening to the bright, perceptive but troubled adolescent Donnie (Jake Gyllanhaal, in the performance that made him famous). He's seeing things, like a 6-foot-tall evil-looking apocalypse-predicting rabbit named Frank and gelatinous blobs that come out of people's chests and point at where they will go next, and then he comes across a book written by the town's resident old crank that seem to explain it all via time travel. All that remains (in the preferred, theatrical cut, at least) are intriguing questions. Is Donnie just a schizophrenic and we're seeing the world from his perspective? Is he a rebellious kid with nothing in his squeaky-clean suburb to rebel against, so he's turned on the universe and its natural laws? Or is he the Christ-like figure, mandated to sacrifice himself for the well-being of others, that the book seems to imply he might be?
23. Grizzly Man (2005)Documentarian Werner Herzog presents footage shot by a guy named Timothy Treadwell over the course of a few years while he camped near wild bears in Alaska and also uses this footage to tell a larger story about man's relationship to nature. Treadwell, it's clear, was going to Alaska and spending his time watching bears to escape his own troubles, frustrations and, we start to sense, mental illness. But in addition to escaping, it seems like Treadwell was trying to impose some kind of order to his surroundings. He named the animals, concocted an entire conspiracy about threats to them and their habitat by the National Park Service (casting himself as the hero, of course), and narrated their lives into a camera, essentially creating a documentary of his own, without a need for an audience. Herzog's film, on the other hand, is something of an anti-nature documentary. Instead of mythologizing and romanticizing the natural world like such films so often do, and like Treadwell himself was prone to do, Herzog accepts nature for what it is: disinterested, cruel and violent. His interest remains keenly on Timothy and the other human characters, how Timothy inspired or troubled them, and their feelings at his eventual demise at the hands of the creatures that so fascinated him.
22. Munich (2005) 
In this era of endless conflicts fought without battlefields, Steven Spielberg's "Munich" is what a war movie looks like. It contains all the intensity and spectacle of combat, all the sober, clear-eyed examination of the horrors of mass violence and all the pleas for rationality and diplomacy that you'd expect from a war film, but the action is brief and contained, the emotions repressed and bottled-up, and the wounds covered and hidden away, never examined and scrutinized. In the aftermath of a terrorist attack on the Olympic Village in Munich in 1972, Israel unleashes a motley crew of various experts and Mossad agents to assassinate the 11 Palestinians they believe were involved. As the team travels around carrying out their mission, and hopelessness about completing their task or moving on with their lives afterward begins to set in, their faith in the righteousness of their calling seems to waver a bit, without ever really giving way. Spielberg has made a critique of serving patriotism and ideology without thinking, but it's a compassionate criticism, never harsh or biting. He's working here at the height of his prowess as a storyteller, commanding our attention through a variety of expansive, note-perfect set pieces and filling his cast with expressive but restrained character actors, whose uniformly stoic turns reflect the morally impossible choices set before them.
21. The Wrestler (2008) 
Sure, "The Wrestler" represents something of a creative peak for Mickey Rourke, and thus a return for a star of another era who has been lost in the woods for a few decades. But there's a lot more going on here than a compelling, realistic and wrenching lead performance. Darren Aronofsky's character study starts in a small-scale, low-key manner, giving us a feel for the quotidian details of aging pro wrestler Randy Robinson's life before piling on the crises and new experiences. Rourke's terrific here as the broken down but still sanguine former superstar, struggling to get by on physically-punishing local gigs and the fading promises of a big-time comeback. Aronofsky so slyly and gradually turns up the heat on his hero, pulling him back out into the world via a romance with a stripper (Marisa Tomei) and a renewed connection to his daughter (Evan Rachel Wood), that we don't realize how high the stakes are and how invested we've become in Randy's health, well-being and relationships until the shattering conclusion. "The Wrestler" ends on exactly the right note, and the effect is sort of mildly pulverizing. It's one of a number of daring choices made by Aronofsky (such as showing us, in gruesome close-up, Robinson's wounds and scars) that really pay off, making this one of the most simple but effective dramas of the '00s.
