Here are the remainder of my Top 10 (2000-2008). These 5 were easier to choose than the others. They are all movies that I knew I loved right after I saw them, and the feeling obviously has not gone away.
Match Point (2005)
I saw this movie in Boston in a big theater, surrounded by a sorority. Good times. I have not seen the vast majority of Woody Allen's movies, but this is probably my favorite. Everything is so crispy made. It feels pristine....even the scratchy recording of Enrico Caruso singing "Una Furtiva Lagrima." The film strikes such a genuine feeling of melancholy. It firmly has a pessimistic view of the nature of luck and human nature. However, its stance is not presented arrogantly. The movie almost represents that person you know who thinks these kinds of things. In that way, the film presents you with a worldview that you might meet in conversation over dinner. How do you respond to it? Watch the movie, and see where your thoughts lead. If I've spoken to you about this movie, then you probably know my one gripe - Scarlett Johansson. I don't really believe her at all. I don't think she isn't trying, but her abilities are just lacking. It doesn't help her cause that all the other characters hit all the right notes with their performances. Love this movie.
Crouching Tiger, Hidden Dragon (2000)
This is maybe the first foreign movie I saw that I really loved. It's so enchanting. I felt swept away to another world. These genre of movies - wuxia - are like the King Arthur tales of China. It blends magic with mystery and a strong sense of values/virtues. There seems to be a lot going on metaphorically, which a non-Westerner would probably have a better time explaining. Michelle Yeoh knocks it out of the park - my favorite performance in the movie. She's also in my favorite fight scene with Zhang Ziyi. When I first saw the movie, I wished there had been more fight scenes, because they were so well made. But, since then I've decided that I probably wouldn't change anything with the movie. My love for it spilled over into the next big wuxia flick - Hero (which is really good too). For me, this is probably the most rewatchable movie on this list.
Pan's Labyrinth (2006)
The genre of this movie is certainly debatable, but I think it is a fantasy movie, or at least a sub-genre of fantasy. It is set near the Spanish Civil War. And probably half the movie is a "realistic" war movie. There is definitely some graphic violence, but less than you'd see in any full-on war movie (at least of recent years). The other half of the movie is a unique fantasy. It is an ugly fantasy world, that is also somehow beautiful. You don't really know who is good or bad, real or fake. Accordingly, the morality of certain actions isn't always clear. This is not a Disney fantasy by any means. While the crazy visuals of the movie are more than enough to draw you in, it was the interplay between reality and fantasy in the same universe that won me over. Again, perhaps not a movie for the squeamish, but one well worth watching, at least for being a genre-bender from one of the most creative directors alive - Guillermo del Toro.
Y Tu Mama Tambien (2001)
Like Pan's Labyrinth, this is a Mexican movie starring Maribel Verdu. I have some extended thoughts on this movie that I'll try to write out soon. For now, I'll say that this movie excels in its simplicity. Three people go on a roadtrip. And for better or worse, the audience comes too. There are some really awkward moments, but each is genuine. The dialogue is wonderful. There is a lot of sex in the movie....apparently. But, I think it's rather appropriate. Overall, this is a movie that loves life. I'll leave my comments there for now.
For a while I described this as my favorite movie. I wouldn't say that today, but I still like it a lot. Dogville is different from all the other movies on my list in a number of ways. One way being that it is a movie that I do not expect anyone else to like. It certainly gives the audience the opportunity to dislike a lot of things. For example, the movie takes place entirely on a sound stage with chalk markings used to represent the walls, etc. that we cannot see. Also, the movie's writer/director, Lars Von Trier, is one of the most arrogant people alive - he's also one of the most messed up. Dogville is very hard-hitting, and it's long too. There is not much action, so it's a movie you have to prepare for, and prepare to just sink into it. I like to think of the movie as almost an allegory. There are a lot of things just begging for interpretation, and I really doubt that there would be a consensus about what the movie actually represents. I would question whether Von Trier even has a strong sense himself. When I saw the movie, it hit a strong spiritual chord. It was a rather personal experience, which is part of the reason I don't expect other people to feel any particular way about the movie. It embodies the kind of film that beckons the audience to either love or hate it. There isn't really any middle-road with Dogville.