The Shining
Full Metal Jacket
A Clockwork Orange
Ferris Bueller's Day Off
Back to the Future
Election
Sideways
About Schmidt
Raising Arizona
Barton Fink
Fargo
The Big Lebowski
O Brother, Where Art Thou?
Reservoir Dogs
Ghost World
Groundhog Day
Duel
Planes, Trains and Automobiles
Toy Story 1 & 2
Those are the films that i always watch. Out of all those, the one i've seen the least is Sideways at around 10 viewings. But it'll soon get much higher than that.