How can you pick 5 films from a lifetime's moviegoing? And how could you judge between say The Italian Job and Singin' in the Rain? So here are some of those I can watch over and over by genre, and in no particular order.
Musical
Singing' in the Rain
Funny Face
An American in Paris
Royal Wedding
Seven Brides for Seven Brothers
Top Hat
Carousel
Action
Dirty Harry
The Italian Job
Zulu
Guns of Navarone
The Good, the Bad and the Ugly
Drama
Gone With the Wind
Inherit the Wind
Compulsion
Anatomy of a Murder
The Glenn Miller Story
Frankenstein (Boris Karloff version)
Western
The Outlaw Josey Wales
Shane
High Noon
The Man from Laramie
Unforgiven
Spectaculars
Ben-Hur
Spartacus
The Vikings
El Cid
Animation
Fantasia
Pinocchio
Bambi
Dumbo
Finding Nemo
Snow White
There are, of course, many, many more.