I started out with an intention to support your post Khev, but as I started thinking through examples, for me personally, even going back to the '40s and '50s there are only a smattering of "great" movies that I would be interested in watching multiple times. I'm sure it varies from person to person, but even looking at Academy Award winners like West Side Story, Midnight Cowboy, and the French Connection, they don't seem all that different from your typical, recent winner in terms of their re-watchability.
Something like Chinatown, Casablanca, Citizen Kane, the Good, the Bad, and the Ugly, the Godfather, or even Big Lebowski or the Terminator doesn't come around every year.
