As sad as it probably sounds, mine's pokémon crystal
Halo... I beat it anywhere between 50-70 times because I played it a lot the first year it came out and beat it about 5-10 every year since. Also I beat the silent cartoghrapher way more then 100 times it is the most amazing level ever... I think I will play it again right now.
Tons of NES, Genesis, and SNES games literally hundreds of times, considering that I''ve been playing some of these games constantly for over twenty years. Notables include the Mario games up to World, the Castlevanias, Ninja Gaiden Trilogy, DKC, Megamans 1-3, and many others.
i noticed recently that i rarely ever finish the same game twice anymore. when i was younger id finish games several times (probably due to not having money to buy my own games so i had to play what i had). anyway, sonic 2! about 11 times! the music man >< the music!
This is a great thread with an interesting variety of answers. The Mass Effect series is getting an awful lot of love and I'm interested in seeing Mirror's Edge mentioned 3 times which makes me really want to go back and replay that. I never finished my second playthrough.
I don't replay games much and I have too many now to justify doing so. I think the most I've played a game is 3 times which goes to at least Plants v Zombies. I think I almost completed Darwinia 3 times and I can't remember if I played HL2:Ep2 2 or 3 times. I've played through HL2 and Portal twice and recently Eufloria twice (mostly played while listening to cricket this winter).
Earthbound is my winner. For a reasonably long RPG, I have beaten that game at least 5 times. Love it.
A lot of my games from my childhood were never beaten or finished, so I didn't fly through much. Maybe the Mario game on Game Boy. Earthbound is the only one that I will totally play today, and it is why my SNES is hooked up in my bedroom while my PS2 and other similar systems are not hooked up at all.
I know it's The Force Unleashed. Not sure how many times though. 20? 30?
Either that or it's maybe Marvel Ultimate Alliance, which I've beaten probably 15-20 times as well.
That's probably it. Most time spent would probably be in LeafGreen. I logged I think over 200 hours on one cartridge, then another 100 hours on another, and didn't beat the game on either.
That's...that's it as far as I know. I haven't even beaten as many games as I have digits, so...