Why these films rather than any of the myriad of other well-deserving films? The criteria are impossible to analyze, but most important are those of beauty and poetry. By beauty I mean the film as an aesthetic whole, including to what extent the film utilizes the language of the medium, merging images, music and sounds. By poetry I mean the way in which the film speaks to us, what it has to say. This does not necessarily mean that the film has to have some sort of discursively developed theme nor does it mean that the film should have a "message" (films of that sort usually have nothing to say - no meaning to convey - no questions to ask). The most abstract film can have something very meaningful to say insofar as it is able to make us see the world anew, to make us wonder. The combination of these two elements, that of beauty that stirs us and poetry that awes us, is what makes film a kind of philosophy.
A last word: These films are, by no means, perfect. They, as any art, contain multiple flaws and kinks that are either directly detrimental to the quality of the film or perhaps add to the film's beauty (flaws - ugliness itself - are a part of the reality of beauty, not her opposite). The descriptions of the films below serve only to highlight some of the more powerful aspects of the film that justify its inclusion on my list. At the same time, these are not simply subjective ramblings about "favorites." There is no difference between subjective and objective when it comes to art (or reality in general). What we see is the reality presented to us, clearly or behind a glass darkly. Our discussion of art is what enables us to see clearer.
10. Ratatouille - Brad Bird, Jan Pinkava
Pixar has created some of the most visually interesting films of the past decade. They are also amazingly unafraid to tackle interesting and important questions about human nature. In a lot of ways the main theme running through their films seems to be that of perfectionism, of growing as a person by transcending the limitations that surround us, be they the norms and standards of society or family (Ratatouille), the trauma of suffering (Finding Nemo) or the temptations of leisure and comfort (Wall-E). Any of the Pixar films could be a worthy addition to a list such as this but for my money it hasn't gotten any better than Brad Bird's Ratatouille. The film is visually stunning, incredibly funny and exciting but also sensitive and sweet, a celebration of courage, friendship and good food.
9. Match Point - Woody Allen
A companion piece to Allen's wonderful Crimes and Misdemeanors, Match Point is a Dostoyevskian meditation on the human soul. Basically a twist on the old tale of Crime and Punishment, the film ultimately puts forth an incredibly bleak and unforgiving point of view, a kind of philosophical "what-if" that is supposed to challenge and disconcert the viewer. Allen has increasingly become a kind of Socratic gadfly in his filmmaking, creating characters that are so self-contained that his films become a kind of laboratory for peeling away the layers of the human psyche. This has to be among his most successful experiments.
8. O Brother Where Art Thou? - The Coen Brothers
I see all of the Coen brother's films being about the same subject: America. Different times, different places, different people, but all inhabiting and forming the "idea" of America. From the trailer parks of Arizona to the bowling alleys of California, the Coen's have shown us different slices of America, usually through a dead-serious sense of humor. Here we have the American South of the early 20th century, filled with saints and sinners, boozers and bluesers, criminals and desperadoes and even the devil himself. Only one canvas is big enough to fit a world so epic, so filled with myth and poesy: That of Homer's Odyssey (never mind that the Coens claim they had not even read the work before shooting the film). The film owes as much to the work of Preston Sturgess as it does to Greek poetry with it's multi-layered story and sense of humor. Yet the Coens accomplish something in this film (as they do, amazingly enough, in many of their films) that Sturgess more often than not failed at (here I incur the wrath of the movie gods): they make you actually care about their characters. The music and cinematography are also especially wonderful in this film, both recreating a real time and place while also transcending it by creating a mythical reality where escaped fugitives turn into frogs and the devil waits at the crossroads.
7. Wonder Boys - Curtis Hanson
A wonderful sweet and sensitive film, unpretentious with a great sense of humor. The performances are very human, based mostly on subtle little observations about people who are basically good and decent but who struggle with their silly little flaws and sicknesses that sometimes put them in a rut. The film is about escaping from those ruts, of breaking free from our stupidity and silliness. This does not mean accomplishing something "great" (like writing the "great American novel") but simply being the best person you can be, filled with love and compassion and embracing the day and the people around you.
6. Good Night, and Good Luck - George Clooney
A near-perfect little film, reminiscent of the great paranoia-thrillers of the 70's. The acting is all silences and glances, inward reflections on human nature, making the invisible visible. Clooney's directing is astounding for its matter-of-factness, its quiet and controlled force. This is a great American film, much better than many of the more high-profile selections of the decade, overshadowing them with its subtlety and poise. An art-house film that is relevant and accessible.