Well, here is a list of movies I think you should have already viewed..
And if you haven't?
GO AND RENT THEM NOW!! I COMMAND YOU!!
I'm not kidding..
I consider these movies to either be essential to function within Pop culture or essential to a normal thinking individual's diet...yum
or something like that.. Movies still in the original font colour are both
And yes, their in no order whatsoever
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Pink Floyd's The Wall
Reservoir Dogs
Pulp Fiction
Higher Learning
Evil Dead
Evil Dead 2: Dead before Dawn
Army of Darkness : Evil Dead 3
The Graduate
Full Metal Jacket
A Clockwork Orange
Star Wars: A New Hope
Star Wars: The Empire Strikes Back
Star Wars: Return of the Jedi
Batman
Apocalypse Now
Schindler's List
Lost Highway
Ghost in the Shell  (Anime..but very very good)
One Flew Over The Cookoo's Nest
Clerks
Mallrats
Chasing Amy
Dogma
Bulworth
Pi

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And here are movies I just highly recommend

Killing Zoe
Natural Born Killers
Event Horizon (Watch in the dark for maximum effect)
Seven
Fear and Loathing in Las Vegas (watch when you're tired, but know you won't fall asleep during it, of course)
Cannibal! The Musical..(after you see this, Ravenous, just to compare/contrast an "indie" film to a "big" one)
Starship Troopers (Silly monster killing movie *Shrug*)
Halloween 1,2, 4, 5, 6
Lock, Stock, and Two Smoking Barrels
Trainspotting
The Princess Bride