There are some films I can watch only once (such as Mercury Rising, or The Birds) not because I think they're bad films, I may really liked them but ... never again.
Then there are films I could watch again and again - and do. These are not necessarily deep films - in fact, terrible writing fraud that I am, I really don't care about "deep" and "important" films.
So here's a non-exhaustive list of films I will happily watch any number of times:
Bill and Ted's Excellent Adventure
The Princess Bride
This is Spinal Tap
Crouching Tiger, Hidden Dragon
The Bourne Identity
The Fifth Element
Never Say Never Again
Toy Story 2
Lord of The Rings
Pirates of the Caribbean (the trilogy)
The significant prevailing element? Humour and character.
What's on the turntable? "Running Hard" by Renaissance from "Turn of the Card"