There are the old SNES games like DKC 1 and 2, Super Mario World 1 and 2, and also one called Mickey's Magical Quest (I think). I have beaten all of those the most, but nothing ridiculous like 100 times.

Pokemon Red - 5 times

DefJam fight for NY - 5 times

Resident Evil 4 - 8 times

Yoshi's Story - 10+ times

That's about it.

@ ArtofAngels

I agree that some may be alittle tricky with their number, but I can asure you that even if Starcraft and Brood War is extreamly difficult and then I mean extreamly difficult It does not take that long I can conplete Starcraft and Brood War on a week why I do it well mostly because I can't get online anymore damn those pirates that are using my three cd-keys arhg. And Starcraft has been pretty long out therefor I have a high number for it.

My second gotta be any of the Civ games they're just time consuming.

 Meuh when I was young I could not afford so many games.  FF was always a must buy and I always wanted to know everything of every game.

I = FF Freak.

I think I also finished RE4 for almost ten times but that is because I started with Easy and then finished it three time to have enough money for all the extra's and then I played it on normal and then on Expert.

Haha big up Mickeys Magical Quest on the SNES :)

Oh oops I forgot...

MineSweeper: at least a thousand times.

I had an addiction for a while. At least 400 times on each difficulty.