I've been around a long, long time, so I'll reply with films that I've seen, all or in part, more than 500 times:
--The GF Trilogy (close to 2000 times).
--Laura (1000 times at least)
--Cavalleria Rusticana (Zeffirelli, almost 1000 times)
--Goodfellas.
--Raging Bull
--Mean Streets
--Seconds (Frankenheimer's masterpiece)
--The Thing (Carpenter)
--The Atomic Bomb Movie (documentary)
--Metropolis
--Nosferatu (Murnau)
--True Confessions
--It's a Gift
--Fail-Safe
--The Wild One
--Bugsy
--Last Picture Show
--Duck Soup
--Blade Runner
--Ten Commandments
--Jimi Plays Berkeley
--Apocalypse Now (and Redux)
--Arguing the World (documentary)
--China Syndrome