Most times I've finished is probably Super Mario Bros. I've had it on the NES, the SNES, the Wii Virtual Console, and on my console-free years I had it on an emulator. Although I completed Sonic the Hedgehog a lot as well.
I never had any friends as a child.
If we're going total playtime, probably Fallout New Vegas. I'm on my fifth playthrough, and it's about 70 hours long and counting. I've finally installed it on my PC as well, to try out some mods (I found a mod that gets rid of Inon Zur's woeful soundtrack and replaces it with music from Fallout and Fallout 2 - YAY), so I doubt I'll stop playing it any time soon. It's a really fun game.
The Night Shade said:
Not kidding here MGS 1 and then MGS 3 and then MGS 2
Matthew94 said:
I beat MGS3 about 13-14 times.
I actually forgot about Metal Gear Solid. I never finished MGS2 and didn't play anything after that, but I got my MGS1 playthroughs down to about three hours. Sometimes I'd see how many times I could finish it in one day if I set the difficulty to Very Easy. I don't know if I finished it as many times as I finished SMB, but I did finish it a good few times.