Damn young people with your hipping and your hopping, and your fancy shmancy collages. I am going old school and just posting a list. I expanded my top 20 into a top 50, will take awhile to get the rest. This is just brainstorming, not my final list.
50. Once Upon a Time in the West
49. Dr. Strangelove
48. The Red Circle -Coolest movie ever.
47. 12 Angry Men
46. Apocalypse Now
45. Battle of Algiers
44. 2001: A Space Odyssey
43. Chungking Express
42. Ikiru
41. Fargo
40. Paths of Glory
39. No Country for Old Men -Still new, but I think its safe to put it here.
38. To Kill a Dragon
37. Waltz with Bashir
36. The Gold Rush
35. Heart of a Dog -A complete masterpiece, despite being a made for TV film
34. Eraserhead
33. Eternal Sunshine of the Spotless Mind
32. Sunset Boulevard -Best movie about the movies
31. The Godfather
30. Rashomon
29. Princess Mononoke
28. Hate
27. Grave of the Fireflies
26. Mr. Death -Best documentary ever made.
25. Ran
24. Dawn of the Dead - Best horror movie ever made
23. The Seventh Seal
22. Brazil
21. Ed Wood - An even better movie about the movies
20. Nausicaa of the Valley of the Wind -Glad to see it on other lists! Best animated film ever.
19. The Good the Bad and the Ugly -endlessly rewatchable
18. My Own Private Idaho
17. Taxi Driver
16. The Supplication -Best combination of poetry and film
15. Grizzly Man -An even better documentary film
14. Pixote
13. Army of Shadow
12. Ballad of Narayama -Says so much about life. You could start a religion
11. Seven Samurai
10. Stalker
9. Peppermint Candy -20th century South Korean history encapsulated in one mans life.
8. Scarecrow
7. Andrei Rublev
6. Naked
5. The Big Lebowski -The most rewatchable movie ever
4. Autumn Marathon -I swear to God its a movie about me
3. The Isle
2. Together
1. Woman in the Dunes -Easily the best movie ever made