Oh damn, so freaking tough of a choice. Man on Fire and High Fidelity are up there, good choices guys. For me, I think it has to be The Big Lebowski, simply because I can watch that movie over and over and over and never get tired of it. It is definately my "if you were stranded on a desert island and could take one movie..." movie... either that or Saving Private Ryan. If I could sneak Band of Brothers in there as a "movie," it would easily be my favorite.
LOTR ROTK Or....KONG. There have been so many great movies. But Peter Jackson's work has been awesome.
I think the best movie of all-time is Billy Madison. Movies should be entertaining enough to be viewed countless times. It'd help if it's a comedy because with thrillers, action flicks, and stuff like that, it gets less and less exciting for the most part after you see it over and over. Comedy, however, some movies you can just laugh over and over at. I'll never get tired of Billy Madison. Honorable mentions to: Happy Gilmore, Half Baked, Man On Fire, Anchorman, Old School, Jay & Silent Bob Strike Back, The Matrix, Wedding Crashers, The Big Lebowski, American Psycho, Dodgeball, Harold & Kumar Go To White Castle, Rounders, Pirates of the Caribbean, Star Wars Epsiode III, Austin Powers 2, and the 40-Year-Old Virgin, Fight Club..... okay I could go on, but I'll stop now.
I'm sorry to be negative, but Star Wars III was awful. Bad acting with a really lazy and predictable script. The whole thing seemed like it was just thrown together with a few corrections made here and there to tie up loose ends. Not that they had any incentive to make a good movie, look how much money they made churning out a piece of crap.
Usual Suspects Napolean Dynamite Garden State American Psycho I can't believe someone mentioned Kong, that was was just terrible in my opinion. But hey if you liked it, cheers to you.