I find the movies I can watch several times are mostly the ones I can relate to, Billy Elliot, Brassed Off, The Full Monty etc. Coming from a mining family in the Midlands I guess this is no surprise, these are followed by other british movies such as Lock Stock, The Crying Game, 4 Weddings, Notting Hill. Next up are some of the foreign films such as Hero and Flying Daggers, then finally the Hollywood stuff such as Lord of the Rings, Bladerunner etc. Most of Clint Eastwoods stuff I really enjoy once but somehow it doesn't have that ability to make me watch it several times.
I'm not saying that Brassed Off is a better movie than Bladerunner, but somehow I can watch it more often. Which movies can you watch over and over?