+4
I have a terrible memory, so I watch a LOT of movies over and over again. Very often, a few months after I've seen a movie, I won't remember the whole movie, but I'll remember that I liked it, so I'll go back and watch it again. Then, after I've watched it a few times, I start remembering it so well that I can quote most of the movie.
The nice thing about having a bad memory is that when I watch the same movie for the second or third time, sometimes it's like seeing a whole new movie, until I get about 3/4 into the movie and all of a sudden I realize that I've already seen it. It also has the advantage of not worrying about reading spoilers because by the time I see the movie, I've usually forgotten what I read about it.
On that note, there are MANY movies that I love to watch over and over again. Some of them are comedies like "Blake Edwards' S.O.B", "My Cousin Vinny", "Liar, Liar", etc. Some of them are musicals like "1776", "Singing in the Rain", "The Music Man", "Oklahoma", West Side Story", etc. Some of them are classics like "12 Angry Men", "North By Northwest", "It's A Wonderful Life", "Arsenic and Old Lace", etc.
But for some unknown reason, my guilty pleasure movie is "The Negotiator" with Samuel Jackson and Kevin Spacey. I don't know why, but if I'm flipping channels and I see it's on, I just have to watch it.