Expanded, more thought-out version of my list, plus changed the 2000 film.
2000: Cast Away - Emotionally stunning with Hanks giving his Forrest Gump performance a run for its money. One of the first three DVDs we ever got, along with X-Men and The Wizard Of Oz. I used watch this again and again. Amazing
Runners up: X-Men, Memento, Unbreakable, Gladiator
2001: Wet Hot American Summer - My most painfully personal favourite movie ever.
Runners up: The Fellowship Of The Ring, Donnie Darko(but really the Director's Cut)
2002: Spider-Man - The most I've ever been obesessed with a single film, my favourite superhero origin, and the definitive movie theater experience of my life so far.
Runners up: The Two Towers, Minority Report, Catch Me If You Can. Great year for movies.
2003: The Lord Of The Rings: The Return Of The King - The Greatest Movie I've Ever Seen.
Runners up: X2: X-Men United(maybe the best directed superhero film ever), Pirates Of The Caribbean.
2004: Spider-Man 2 - Probably the strongest installment in my favourite comic-book film franchise. Epic.
Runners up: The Incredibles! Harry Potter 3.
2005: Batman Begins - An amazing year for movies, but of all the best, this is the one I'm closest to.
Runners up: V For Vendetta is a VERY close second, War Of The Worlds, The Matador, King Kong, Goblet Of Fire.
2006: Blood Diamond - I'm usually kind of bored by this sort of film but this was so good and touching. DiCaprio is excellent. I already really liked it, but when we ended up studying the diamond trade in both Law and Economics in 12th Grade and all watched this film about four times between the two classes, it became even more special.
Runners up: Casino Royale, Pirates Of The Caribbean 2, Babel(which should've won Best Picture and Supporting Acrtess).
2007: Zodiac - So ridiculously thorough, incredible cast, Jake Gyllenhaal being used to perfection. I've seen this four times. I think that's the only 3-hour non-LOTR film I can say that about. Also, the movie that made me love Robert Downey Jr.
Runners up: Spider-Man 3, NCFOM, There Will Be Blood, Live Free Or Die Hard
2008: In Bruges - This year had a lot of really good movies, but In Bruges was the only one I felt was actually great. I haven't watched it again since before actually going to Bruges, but I look forward to it.
Runners up: The Dark Knight, Iron Man, Slumdog Millionaire
2009: Inglourious Basterds - The most impressed I've been by a film since 2005. An absolute, glued-to-the-screen, stand-up-and-cheer masterpiece.
Runners up: District 9, The Brothers Bloom, Knowing, Half-Blood Prince. I still haven't seen a couple of prominent Oscar films, so here's hoping they'll make it too.