Back in the day, Ninja Gaiden II (one of the few that I owned, as we did not have a lot of money for games), probably a few hundred times. Then Contra, Mario 1, Predator, all on the NES and all in the hundreds. Moving to the SNES, then Street Fighter II for sure, followed by SM World (I would always show people how to use the shortpath to the ending). Coming to 3D, I guess SM64.
My 1000th post: https://gamrconnect.vgchartz.com/post.php?id=9368779