Version 2.o
I'll admit it. The last version of Name That Movie! was dang hard, so naturally I'll do the same one again - but with two more hints. (By the way, good try Squish but not quite right.)

Hint#1: Our hero (not shown), probably wishes he just wrote a memo.

Hint#2: Brought the term "caterpillar" back into the water.

Hint#3: Features the most Scottish Russian ever.

The Picture: