Now here's where things get interesting. After a well-thought out process I selected what I felt was the best film of the decade and Sean Penn's Into The Wild was left standing with 2000's Wonder Boys coming in a very close second. Most surprising to me was the beating they gave the rest of the films I considered, many of which had underwhelming viewings when I revisited them. I may have raised a few eyebrows in saying that compiling this was difficult not because there were so many incredible films to choose from, but so few. My top two were definitely bridesmaid picks, with neither placing high (or at all) on most decade lists, while I'm also guilty of not naming either the best film of their respective years. This happened a lot as films I was SURE would easily crack the top ten missed that short list by a wide margin, and in some cases, even missed the longer one below. Others, some of which didn't even put in a good showing for me when I first viewed them, really came through when it counted. It kind of makes me wonder the point of compiling an annual "best films" list when there's just no predicting how the movies will age years or even just months from their time of release. 2008 had a major shake-up to the point where I'm unsure whether I'd still consider The Dark Knight that year's best. But that's the test right there and a reminder of why watching and re-watching them can be so fun. While I disqualified movies released in 2009 from the top 10 on the basis that it's just too soon, I took them into consideration for this longer list. As a result, a few made it.
I'm using the term "RUNNERS-UP" very loosely because, in all honesty, very few of these came close to making it. Despite my backhanded compliments, I really do love the films below and this should answer a lot questions anyone may have had as to where I stand on certain popular (and unpopular) titles, based on their inclusion or exclusion here. Of course, I didn't see EVERYTHING but I didn't "accidentally" leave anything off either (I'm looking at you Eternal Sunshine of the Spotless Mind). There are some surprises, a few of which I feel needed a brief explanation, so I gave it. Others I just wanted to comment on for one reason or another and a few those comments aren't all positive. Rather than rank the remaining 40 films (it would probably change in a week anyway), I've opted to put them in alphabetical order, bolding the titles that at least came closest to cracking the top 10.
A.I.: Artificial Intelligence (2001, dir. Steven Spielberg)
Spielberg's most ambitious effort in years and definitely not the poor man's Kubrick it's been accused of being. Don't let anyone try to tell you its ending isn't tragic. Starting to get some respect, but still criminally underrated.
The Assassination of Jesse James by the Coward Robert Ford (2007, dir. Andrew Dominick)
Brick (2005, dir. Rian Johnson)
Cast Away (2000, dir. Robert Zemeckis)
Sure, the trailer and commercials gave the entire plot away before anyone saw it (which was just wrong) but at least there was something special to give up. How many films would have just ended without a resolution at all, much less going the extra mile this one did for the finale? Gaining then losing fifty pounds and acting opposite only a volleyball, Hanks' performance is a miraculous physical and emotional transformation he still gets too little credit for.
Crank (2006, dir. Mark Neveldine/Brian Taylor)
The Curious Case of Benjamin Button (2008, dir. David Fincher)
Despite script problems (I admit it), it STILL makes this list, which should not only give you an idea how little I think of this decade, but also how skilled a director Fincher is in being able to cover for it. Certainly holds up better than Best Picture winner Slumdog Millionaire from the same year.
The Dark Knight (2008, dir. Christopher Nolan)
Surprisingly, this didn't even come close to the top ten and had its messiest viewing yet. Maybe I've seen it too much because the more I watch, the more I think we (I) over-analyzed and overestimated it. But Ledger's performance hides most of the flaws and takes it over the top. A great superhero movie with more on its mind than most. We'll leave it at that.
The Door in the Floor (2004, dir. Tod Williams)
One of the strangest third acts I've seen, breaking every screenwriting rule in the book. And maybe the second or third best performance of Jeff Bridges' career. Also, an awesome closing scene.
Dogville (2003, dir. Lars Von Trier)
Elephant (2003, dir. Gus Van Sant)
(500) Days of Summer (2009, dir. Marc Webb)
The 40-Year-Old Virgin (2005, dir. Judd Apatow)
Hard Candy (2005, dir. David Slade)
Deeply disturbing, but unforgettable, and it'll leave you thinking. Introduced the world to the talented Ellen Page, which IS a good thing, despite what you've heard.
I Heart Huckabees (2004, dir. David O. Russell)
I'm Not There (2007, dir. Todd Haynes)
The most inventive biopic of the decade, but I already have what I consider the definitive Bob Dylan film in the top ten with Wonder Boys. Yet more proof of how rich a year '07 was.
Inglourious Basterds (2009, dir. Quentin Tarantino)
Kill Bill Vol. 1 & 2 (2003/2004, dir. Quentin Tarantino)
I counted them as one entry, but I still say Tarantino made a BIG mistake splitting them up. A carefully cut single film could have resulted in a masterpiece.
The King of Kong: A Fistful of Quarters (2007, dir. Seth Gordon)
The documentary of the decade. And I don't even feel the slightest bit guilty for being on the edge of my seat with suspense over the Donkey Kong world record. I'd put Mullet-sporting, hot sauce king Billy Mitchell up against Heath Ledger's Joker in terms of pure villainy any day of the week.
Little Children (2006, dir. Todd Field)
Lost in Translation (2003, dir. Sofia Coppola)
Michael Clayton (2007, dir. Tony Gilroy)
Now THAT'S how you end a movie. Why can't all movies have a final scene as satisfyingly as this? Chills every time. Gilroy actually knew what we wanted and gave it to us. I'm shocked how well this airtight, legal thriller holds up on repeated viewings. Easily the best work of Clooney's career.
Memento (2000, dir. Christopher Nolan)
Moon (2009, dir. Duncan Jones)
Mulholland Drive (2001, dir. David Lynch)
The New World (2005, dir. Terrence Malick)
The movie James Cameron wishes he could make. But with real people and actual scenery. And this coming from someone who actually liked Avatar. As far from a history lesson as is imaginable, this film engulfs you in history, allowing you to see and share the experiences of the characters, but more importantly, feel them. Didn't get what the big fuss was about at first, but now I do.
No Country For Old Men (2007, dir. Coen Brothers)
Phone Booth (2003, dir. Joel Schumacher)
Yes, Phone Booth. Not a misprint. No joke. One of the most underrated films of recent years and for me the thriller of the decade. The premise is ingenious and its execution by Schumacher and writer Larry Cohen comes dangerously close to living up to it. So many ways this could have gone wrong, but doesn't as we're held captive for 80 suspenseful minutes in a single location. Did you know this was originally Hitchcock's idea? Endlessly rewatchable.
Primer (2004, dir. Shane Carruth)
Requiem for a Dream (2000, dir. Darren Aronofsky)
Revolutionary Road (2008, dir. Sam Mendes)
Another movie James Cameron wishes he could make. Jack and Rose in Titanic actually didn't have it that bad compared to these two. The film, which at the time seemed more like a performance showcase for Kate and Leo than a project of lasting value, stayed with me a lot longer than I expected. Then again, I'm a sucker for depressing suburban dysfunction. Hit close to home (maybe TOO CLOSE) for many, bringing up the frightening possibility that much hasn't changed since the 50's and we've essentially become our parents. The period detail is scary. Still don't understand how anyone can complain that they "hated" the main characters. At the risk of being overly cynical, would that mean we hate ourselves?
The Royal Tenenbaums (2001, dir. Wes Anderson)
If I had to pick, this would be number 11 and came closest of all the films to making the top 10. So, why didn't it make it? No real faults to speak of and if you get me on the right day, I might even say it's better than either Adaptation or The Squid and the Whale, but it seeming almost interchangeable with those two couldn't have helped its chances. Often imitated (poorly), no film has had a greater aesthetic or storytelling influence this decade. With Anderson, you're either on board or not. If it's okay with you I'll just consider this, not Welcome to Mooseport, Gene Hackman's final movie before retiring.
The Rules of Attraction (2002, dir. Roger Avary)
Saw (2004, dir. James Wan)
Not as harmed by its many inferior sequels as I thought it would be. But yes, they should have stopped at three (or maybe one depending on who you ask). It's the 2004 original that's a carefully constructed mystery/suspense thriller of the highest order rather than "torture porn," and why I keep getting suckered into coming back for more. In the succeeding films, Tobin Bell is excellent as one of the few movie villains given actual motivation, as sick and twisted as it may be.
Synecdoche, New York (2008, dir. Charlie Kaufman)
Adaptation kind of took its spot as the premier Charlie Kaufman entry on my list and part of that may be that I'm STILL trying to make sense of this. But that I continuously want to is very good news and the latest viewing was a trip. Ironically, given its themes, I can see it aging really well. It's already starting to.
25th Hour (2002, dir. Spike Lee)
Can't stand Spike Lee's movies. At all. I never thought he made a good one, much less a great one. Except for this. It's held up exceptionally well, gaining traction by the year. And to think we thought it was a bad idea at the time to release a movie even referencing 9/11. Maybe it was then. Not now. There are no words that accurately convey the power of the film's final fifteen minutes, and nearly every minute before that.
Vanilla Sky (2001, dir. Cameron Crowe)
Alright, so the whole thing with Tom Cruise's facial disfigurement, lucid dreams, cryogenics and all that stuff is a bit (okay, a lot) more ridiculous than I remember, but it is still a great, crazy kind of ridiculous. You have to give it up to Crowe for the audacity of it all. Playing a psycho strangely suits Cameron Diaz. Must-own soundtrack of the decade.
The Virgin Suicides (2000, dir. Sofia Coppola)
Wall-E (2008, dir. Andrew Stanton)
Where The Wild Things Are (2009, dir. Spike Jonze)
The Wrestler (2008, dir. Darren Aronofsky)