Mass Effect 1...I've beat that game at least 13 times. Twice on the PC, all the achievement finishes for two separate xbox live profiles which is like eight each, and 3 more for different choice lines for ME2. And I've only beat ME2 four times and ME3 once...depending on the extended cut of ME3 I will play it more.
Chrono Trigger/Cross, Final Fantasy 9, Divinity 2 Dragon Knight Saga, Radiant Historia and Zelda (all) are on my list of multiple finishes. Putting them on a list makes me want to revisit more of them but there are just too many good games right now that going back is almost a waste of time.