Dr Strangelove. Cause, well Peter Sellers and Stanley Kubrick at their best in a darkly, at the time chilling, black comedy about the extinction of the human race at the hands of madmen and incompetents? Not to mention the bomb ride.

Also "MEIN FUHRER I CAN WALK!"

Speaking of Fuhrers, The Great Dictator was pretty awesome too, and definitely recommended for anyone with an interest in old, old cinema. We watched that over a few history classes in high school. Still need to get me a copy of my own.

The Truman Show is a favourite of mine as well, it also is pretty impressive when you relate the subject matter to when it was made, almost prophetic really.

After watching the already recommended Romero movies watch Shaun of the Dead.

Most of the rest of mine have already been covered but I'm gonna add Bill Murray's comedies as well especially Stripes and Ghostbusters.

Hmmm... lemme think.

http://www.brawlinthefamily.com/images/HomageWALLE.jpg

It's a fantastic story that makes you wonder how far an AI could really go in independent thought, all while being as charming as it could possibly be.

That, and it makes standing up EPIC.

European movies.
Le Fabuleux Destin d'Amélie Poulain is one of the best romantic comedies ever. It just has so much charm in it.
Life of Brian is best Python film. Good satire, it has George Harrison in it and Always look on the bright side of life is song which is made of awesome.

American stuff.
Fear and Loathing in Las Vegas is wonderful movie and you know it.
Indiana Jones and the last crusade as it's probably the best of those films and one should really see one of them at least.
And I don't remember this one that well, but The Fisher King seemed to be good movie. It has been so long time and I would love to watch it again.

And I really should watch some movies mentioned here. Or more movies actually.

No, Southland Tales is the best movie movie of our generation. Period. We've been over this.

Arsenic and Old Lace & Bringing up Baby are two of my all time favorite old comedies, and are always worth a watch.

I guess I should pitch some in.

Anything by Hayao Miyazaki. Especially Whisper of the Heart. It's a really sweet romance type story that I never get tired of. Also, Castle in the Sky and My Neighbor Totoro.

Go. It's a strange, hilarious, and wonderful movie. It tells the perspective of several different characters in odd, akward, and downright moments that you have to watch to really appreciate.

Falling Down. Because the life of a business man in the city gets rough, and shit happens. Shit gets real.

Paprika. It's like watching a dream, and it only makes sense to a certain point, but in a good way. Plus the music is bitchin'.

Since greed mentioned The Great Dictator, I figure I ought to mention some good films by the Marx Brothers. While most of their films have at least one or two really hilarious moments to recommend them (with the possible exception of The Big Store), I for one think the best movies they made are Animal Crackers, Monkey Business, Horse Feathers, Duck Soup, and A Night at the Opera. (I know those last two get recommended a whole lot; but I personally prefer the first two. Of course, your own mileage may vary.)

You generally don't go into a Marx Brothers film looking for a complex and densely layered plot; nearly all the humor is generated by the characters of the Marxes, and the plot just sort of guides them from one set-piece to the other. But they're some superlative set-pieces, and well worth watching.

I forgot that one, that was really a great movie.

Also I'm gonna recommend Apocalypse Now. Just how many things made since reference it is pretty incredible.

Quite a few to choose from for a should watch list:

Moulin Rouge! - Funny, Entertaining, Musical and terribly terribly sad.

Lord of the Rings- Long, epic and dramatic story telling. Too bad that the Hobbits are Cornish and that the last film just won't end!

Blade Runner- Cyberpunk Cult Classic.

Snatch - Funniest and most entertaining film from the Guy Ritchie collection, in my opinion.

Predator - Alien Hunter? Marines? Arnie? Explosions? What more do you want!

The Thing - Still a classic horror film even by today's standard.

Godfather I & II - Powerful film and story telling: Don't bother with the third one.

Lethal Weapon Series - Action & Comedy Packed Detective film. Favourite character Mel Gibson has played.

Beverly Hills Cop Series - Same as above, but more comedy inclined. Replace Gibson with Eddie Murphie.

Hot Fuzz - Parody of the above films, set in Merry 'Ol England: The West Country (Aka. Farmer land)! Oo' Arr.

People have already beaten me to the other film I was going to name, inconceivable!