For me, this is an evergreen subject. I'm one of those who can watch favourite movie over and over again, without being fed up. The same goes for books and games. Not to mention the music. I never could understand people with "I saw-read-heard-played that one before" attitude. A good piece of music, cinema and read is IMO timeless, and should be something that one can enjoy for many times, instead of just chewing it up once and then spitting out. Of course, that nothing can be compared to the thrill of the first time. But, on the other hand, the second time is often far more revealing and rewarding experience. And every further consumation is like with a good wine: it gets better with age.
Back to the original topic. I've replayed my favourite adventure and other games several times so far, but I tend (especially with adventures) to make very long pauses between the replays. I think this is a key factor of enjoyment when replaying a game. The same goes with film and literature. With music, for me, at least, things are a bit different.
