Shadow of the Colossus holds the record for me at 6 play throughs. I rarely play a game more than once, twice if it was really good.
Though, when I was younger, I did play a game called Dog's Life about 9 times. But that game is really easy and it got to the point that I could easily beat it in about 2-3 hours, so I don't really count it.
Demon's Souls- at least 15
MGS2- 10 at least
MGS4-8
Sonic 1- 4
Sonic 2- maybe 10
Sonic 3- 7
Armored Core: For Answer- 4
Gundam Crossfire: 8 or 9, maybe 10
Streets of Rage- 13
Golden Axe- 1 hard fought time
Special mentions to Rome: Total War, and the Mount&Blade series. They don't really end, but I played them a LOT.
But single most playthroughs goes to MGS3 with between 25-30, likely more.
Since I go back to before the NES, I'm just going to use 20 times for some of them
Batman(NES)- 3
Super Mario Bros.:- <20
Metroid: <20
Mike Tyson's Punch Out!!: 20
Castlevania 3 >20
Super Mario Bros. 2, 3 >20
Super Castlevania 4- 5
Super Mario World- 5
Comix Zone- 2
Turtles in Time- >20
Batman Returns(SNES)- 4
Batman (GEN)-3
Batman Revenge of the Joker (GEN)-2
Batman Returns (Gen)-2
Donkey Kong '94- At least 3 times
Jeez, I could be here all night. Before the mid 90's we didn't have a way to resell or trade games here so we just replayed them all over and over again.
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