Clerks and Pulp Fiction were the only two I've ever seen more than once in a theater. That said, in regard to the former it's because I was working in a Quick Chek at the time so it was all pretty relatable.
Embarrassed to say, but I saw The Village twice. Once with friends, and the second time on a first date because the girl wanted to see it. She made sit through that movie and still didn't give me any....insult to injury.