1) Dr Strangelove: Simply the best comedy ever. A comedy about the cold war and sex. I catch another little joke every time I see it. Kubrick is a genious
2)Caddyshack: This is a hybrid. This is a cross, ah, Bluegrass, Kentucky Bluegrass, Featherbed Bent, and Northern California Sensemilia. The amazing stuff about this is, that you can play 36 holes on it in the afternoon, take it home and just get stoned to the bejeezus-belt that night on this stuff. Here, I've got pounds of this.
3) Stu, if you like
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Originally Posted by Perfect Stu
2. The Great Escape
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Go rent
Stalag 17: The movie (and the play) were the basis for Hogan's Heros. Stalag 17 is far more serious, even though it does contain much of the comedic genious of HHs.
4)The Untouchables: One of Sean Connery's best films. There's not much I can say about it except see it for yourself. It's great.
5)Thirteen Days: There's so many I'd love to put here, but I'm going with a personal favorite. The acting is so good in this movie and for someone who didn't get to actually live through the period the fear is still very real.