I try to play Alan Wake once a year, it's like returning to my favorite movie, it just feels comfortable cruising into Bright Falls on that barge.
Not really. I think there are maybe less than five games I've played through more than once in my entire life.
Shutokou Battle 2, AKA Tokyo Xtreme Racer 2 on Dreamcast
There is something about this game that makes me play it again, and again, and again. I play with a different car each time, abusing the dumb AI to beat the otherwise hard bosses.