I've been working on this list for awhile, and I'm still not entirely happy with it. I didn't want to put in the work to make a top 50 list, but I was similarly unable to cut it down below 30. While I think all of these films are objectively great, and I could make a reasoned argument for each, a lot of this is based personal favoritism as well.
My 14-year-old brother read this list and said, "God, you're such a snob, Ashley. No one has seen these movies, no one knows what you're talking about, and I don't see Pineapple Express on here, so you're an idiot."
30. Dancer in the Dark (2000, dir. Lars Von Trier)
Björk is, admittedly, not to everyone's taste as a singer. But her performance as a Czech immigrant fighting to save her son's eyesight in 1960s rural Washington is endlessly compelling and tragic. It's also an interesting and rather postmodern approach to the musical, proving that the genre can survive into the 21st century.
29. Good Bye Lenin! (2003, dir. Wolfgang Becker)
Though Daniel Bruhl wasn't really on anyone's radar in the United States until Inglourious Basterds, the film that solidified his German and international stardom was Good Bye Lenin!, a charming film about a young man trying to recreate Soviet East Berlin for his GDR-enthusiast mother, who came out of a coma shortly after the Wall fell.
28. The Dark Knight (2008, dir. Chris Nolan)
The most memorable part of the The Dark Knight is undoubtedly Heath Ledger's performance, but the film as a whole more adequately captures the dark, morally ambiguous tone of the comics on which it was based than did the bubblegum jingoism of the Spiderman trilogy that preceded it.
27. Best In Show (2000, dir. Christopher Guest)
Christopher Guest's mockumentaries nearly always deliver, especially with the strength of his cast. But Best In Show is particularly adept at capturing the obsession and quirks of personality involved in competitive dog shows without being mean-spirited.
26. High Fidelity (2000, dir. Stephen Frears)
Based on Nick Hornby's novel, High Fidelity relocates the story of a lovelorn music fanatic from England to the United States. With the exception of School of Rock, it represents one of the last times Jack Black was utilized well in a movie, and John Cusack is perfect as a jaded reboot of Lloyd Dobbler.
25. In Bruges (2008, dir. Martin McDonagh)
Martin McDonagh has been writing dark, dark comedies for the stage for decades. In Bruges was his first foray into film, and not surprisingly, his brilliant humor translated well on screen, particularly in Colin Farrell's standout performance as a guilt-ridden hitman.
24. Once (2005, dir. John Carney)
A no-frills movie, filmed mostly on a handheld, that captures all of the magic of a classic musical without the superficiality. Also, you really can't beat The Swell Season.
23. Oldboy (2000, dir. Chan-wook Park)
A tightly-wound, often horrifying portrayal of a man's pursuit of revenge. One of the most interesting elements of the film is the richness of the mise-en-scene; each backdrop is imbued with detail layered over detail.
22. Moulin Rouge! (2001, dir. Baz Luhrmann)
There's not much that hasn't been said about Moulin Rouge! It totally indulges in its spectacle, and Ewan and Nicole are fabulous and tragic. The entire film can really be summed up in three words: Elephant Love Medley.
21. Kill Bill Vol 2 (2004, Quentin Tarantino)
I love both volumes of Tarantino's revenge masterpiece, but I have a slight preference for Volume 2. It adds the much-needed emotional depth that Volume 1 was always building towards. By the time Bill tells Beatrice that she's his favorite person, I'm always in tears.
20. Far From Heaven (2002, dir. Todd Haynes)
Todd Haynes' brilliant homage to Douglas Sirk's melodrama All That Heaven Allows, complete with saturated, dramatic colors and a particularly brilliant performance by Julianne Moore.
19. Pan's Labyrinth (2007, dir. Guillermo del Toro)
This film has grown on me with repeated viewings, and now I think I can look at it objectively as a masterpiece. It strikes the perfect balance between period piece and outlandish fantasy.
18. Little Miss Sunshine (2006, dirs. Jonathan Dayton & Valerie Faris)
Rarely has an ensemble cast been put to better use than they are in this movie. A pitch-perfect family comedy and easily one of the most memorable films of the decade.
17. Hable con ella (Talk To Her) (2002, dir. Pedro Almodovar)
Almodovar does the unexpected in making his audience sympathize with Benigno, whose actions become more and more disturbing as the plot unravels. Unlike most of Almodovar's movies, Hable con ella focuses more on its male characters than its female ones, and to great effect: the film is a fascinating psychological study of relationships.
16. Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006, dir. Larry Charles)
Sacha Baron Cohen transcended the unevenness of Da Ali G Show to make a movie that is not only unbelievably hilarious and shocking, but which also offers some of the most scathing criticism of the United States in film history. For a brief moment, Borat captured the national zeitgeist in all of its paranoia and self-indulgence.
15. Mullholland Dr. (2001, David Lynch)
I just saw this movie last night, and while I'm still mulling over its finer points, I'm confident in its brilliance. One of the only films in recent memory that successfully pulls of a "twist" with intelligence, Mullholland Dr. is tense and absorbing through to the end.
14. American Psycho (2000, dir. Mary Harron)
Easily the stand-out performance of Christian Bale's career, American Psycho is a perfect satire of 1980s consumerism and self-obsession in all of its bloody glory.
13. Shaun of the Dead (2004, dir. Edgar Wright)
Genre (and auterist) homages can go horribly wrong, but in the case of Shaun of the Dead, Edgar Wright got nearly everything right. The movie is hilarious to zombie fans and the uninitiated alike, and single-handedly created the genre known as romzomcom.
12. City of God (2002, dir. Fernando Meirelles)
A brutal portrayal of life in Brazil's drug-fueled favelas, City of God's brutality is matched only by is brilliance. The cinematography in particular is stellar.
11. Let the Right One In (2008, dir. Tomas Alfredson)
Basically defines the word "atmospheric." It's a story of childhood love and companionship set in the dark, snowy landscape of small town Sweden. Oh, and there are vampires.
10. Y tu mama tambien (And Your Mom, Too) (2001, dir. Alfonso Cuaron)
At the time of its release, Y tu mama tambien was viewed primarily as a movie about sex, which neglects all of the smart political commentary throughout. Though Heath and Jake's kiss was a big deal, at least it was anticipated - the kiss at the end of Y tu mama tambien was the shot heard 'round the world. Or at least Mexico.
9. Das Leben der Anderen (The Lives of Others) (2006, dir. Florian Henckel von Donnersmarck)
Another, yet very different, movie about East Berlin. A spy for the GDR becomes invested in the lives of those under his surveillance, and what ensues is one part thriller, one part historical exploration. The brilliant script is bolstered by equally brilliant performances.
8. Brokeback Mountain (2005, dir. Ang Lee)
Beautifully shot, as well as faithfully adapted from Annie Proulx's short story, Brokeback represents another high point in the tragically short career of Heath Ledger.
7. Le fabuleux destin d'Amélie Poulain (Amelie) (2001, dir. Jean-Pierre Jeunet)
If happiness were a movie, it would be Amelie. Totally enchanting and totally French.
6. The Royal Tenenbaums (2001, dir. Wes Anderson)
Wes Anderson made several brilliant films this decade, but Tenenbaums stands above the rest, because really, what better subject for a film than a family of child prodigies? One of the most intelligent and hilarious films of not just the decade, but of all time.
5. Eternal Sunshine of the Spotless Mind (2004, dir. Michel Gondry)
Prior to 2004, I would have doubted that any movie starring Jim Carrey would make it onto anyone's top movie list, let alone my own. But he's understated and thus, far more tolerable and believable as a man tormented by the idea that his ex-girlfriend has used a new technology to erase her memories of him.
4. The Departed (2006, dir. Martin Scorsese)
A surprising but much deserved Best Picture win, The Departed is Martin Scorsese's best work since Casino (or, if I may be so bold, Goodfellas). All the way through, the movie captures the insanity of the Whitey Bulger era of organized crime in South Boston, as well as utilizing elements of Greek tragedy to bring about its shocking conclusion.
3. Children of Men (2006, dir. Alfonso Cuaron)
One of the most underrated movies of the decade, Children of Men is amazing on all levels. Its cluttered and dark mise-en-scene, the intensity of Clive Owen, and the chaos of a world without reproduction come together to do what V for Vendetta attempted, but with more subtlety, nuance, and intelligence.
2. No Country for Old Men (2007, dir. Joel and Ethan Coen)
No Country is a film primarily about fate, which is part of the reason I find it to be more interesting than the average crime story; it's not about wit or evidence, but about trying to escape a strange and horrible destiny.
1. There Will Be Blood (2007, dir. Paul Thomas Anderson)
This movie is EPIC in every possible way. I have such high hopes for P.T. Anderson's next project, because everything he's made so far has been mindblowingly awesome, especially There Will Be Blood, which features Daniel Day-Lewis as one of the most fascinating characters in cinematic history, oil prospector Daniel Plainview.
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