Meh, it depends. In my youth I used to go and watch films at the cinema multiple times. I even (don't ask me why, I have no fucking idea) saw Tomb Raider five times - even though its a god awful piece of shit.
Nowadays though, I feel like I just cant invest the effort into watching things multiple times. Its different for films and TV though. I've recently started watching 24 again from the very beginning, and season 2 was always kinda my favourite. But by god was it a grind to get through.
It all depends on how much I enjoy a particular thing. Horror's and Comedies are the worst, because they only have a finite shelf life, before they stop being scary/funny. There's only so many times you can watch ringu before it gets really really boring with no payoff, and I dread the day when Hot Tub Time Machine stops getting a laugh outta me.