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halo 3-probably a good 10 times, mostly co-op.

Pokemon Red/Blue-probably 10 times. Some people enjoyed trying to catch them all. But when I was a kid I would always restart as soon as I beat the game and try and beat it again with a completely different team. 

Halo Reach-twice. Once Solo and once Coop

Super Mario Bros-Dozens of times. 

Super Mario World-Dozens of times.

Crash Bandicoot-around 3 times I think.

Wind Waker- Twice

And thats about it, unless you start counting games with pseudo campaigns like mario kart/super smash bros