I could watch Against All Odds about once a year. James Woods is great in it. It's got a good story, intrigue, my home town, some tropics, sports, and a lot of corruption. And another fantastic wordless ending scene (although assisted by Phil Collins's lyrics somewhat).
Movies that I have dropped other things to sit down and watch more than once are the silly ones like Airplane and Naked Gun, and of course the Shawshank Redemption, which seems to play once a week on TV somewhere. Of course, I would watch Morgan Freeman read the phonebook. (Sadly, each time I watch it, Timmy is collecting another dime for some leftwing cause...)