Okay so here is my 5. I've gotta note though, that this is my Top 5 HOLLYWOOD pictures, not Top 5 all time, cus i find it too hard and pointless to arrange movies from different schools together. Besides hollywood cinema, I am a sucker for american independent, asian and soviet cinema. This being said, here is my Top 5 Hollywod flicks all time
Terminator 2 - the movie that has been there all my life and pretty much shaped my understanding of film. A breakthrough originally, it is still damn bad-ass. A great sci-fi flick and in my opinion the greatest thing Cameron has created.
The Truman Show - an amazing emotional journey with Jim Carrey, on par with also amazing The Eternal Sunshine of the Spotless Mind. Full of detail, and cool acting/directing. I love it.
The Dark Knight - well, we all remember our first time seeing it in theater. Nolan's best film, and yes I have seen Inception. This movie is just too good.
Kill Bill - this movie is pure coolness. As Tarantino himself pointed out, Kill Bill is not a life-film, but a film-film, aka the kinda film that Vince and Jules see when they go to movies. Its got great story and look, humor, action and even an anime chapter. In every frame of this movie i can sense the filmmaker's love for the art of motion picture. Pulp Fiction for the critics, Kill Bill for me.
Sin City - and my number one favorite hollywod title is this totally stunning comic-book noir movie. Superb cast, dialogue and directing. Its even got a scene by Tarantino. Eveyone who loves this movie knows perfectly everything thats good about it, so no need for me to go there. This movie just totally clicks with me.
Other Hollywod films that i really like but that dont make it to top 5 are Space Odyssey 2001, Watchmen, V for Vendetta, The Eternal Sunshine of the Spotless Mind, Speed Racer (you heard it right), Ed Wood, and Lost in Translation. Also, though probably not technically hollywood, The Hard Candy (w/ Ellen Page) and Green Street Hooligans (w/ Elijah Wood) are also two great movies. If you havent seen some of these, i strongly recommend them all.