Street Fighter 2, Civ 2, Super Mario Bros 1 and 3 ,and Sonic 2. I’ve probably finished those games over 100 times each. Maybe several hundred times as I’d play the crap out of them when I was a kid, often multiplayer - and Sonic 2 and Mario 3 I still play through probably once a year each. Probably a few dozen for Mario Kart, Streets of Rage, and Ninja Turtles games - multiplayer ones out of those. Link to the Past has to be a few dozen times as well, the game isn’t that long, I can complete it in an afternoon.
I’m more of an RPG guy, I’d guess I’ve probably done 30+ times for Chrono Trigger (not sure how to count this one as some pathways are much shorter than others, the game isn’t particularly long even on the longest path), I’ve done FF6 three times since just the Pixel Remaster. For the ultra-long ones, Witcher 3 five times (I think, might be more), I’m playing a Death March game right now.
I describe myself as a little dose of toxic masculinity.