Hmmmm I don't if any of these have been mentioned before but here is some that I would watch again:
"
Brazil" - Terry Gillam!
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Fear and Loathing in Las Vegas" -cliche I know
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Wizards" -from 1977
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The Jabberwocky" - semi monty python-ish
"
Time Masters" -1982 (French?)
"
Transformers" - 1986 (It's ch-ch-ch-cheesy, but it has Planet eating space god and a great crowning ceremony scene (
http://www.youtube.com/watch?v=U4iwY2LXhz0 ), that I'd love to see reproduced elsewhere. And for some reason the Spacy environments in Starcraft 1 always reminds me of back ground art from this movie.
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The Good, the Bad, and the Ugly" - 1966 Apparently is a trilogy, but I have yet to see them all.
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High Noon" - Another Western that might not be as popular today
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Lawrence of Arabia" - 1962
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Treasure Island" - 1990 No Orsen Welles, but a good cast, from what I remember?
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Excalibur" - 1981 (So bad, but so very awesome.)
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Princess Bride" - I don't know if I should admit this with a name like that, but it is a good movie regardless. The book although different may be better?
Alfred Hitchcock movies?
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Manchurian Candidate" - 1959
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Young Frankenstein" - Mel Brooks film, maybe throw in "
Blazing Saddles" too?
"
Top Gun"? - hahaha

I can't stand Tom Cruise, but this one is a classic about my beloved period of the 1980s.
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Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb" - 1968
As you can see I haven't seen too many recent films that have really caught my attention.