For retro games it probably would be Batman on NES. I'm currently trying to beat Castlevania and Megaman 2.
For modern games it would be GTA 3.
Let's hear your stories!
Edit: Thanks for all the replies, you guys have conquered some pretty tough games, some I haven't even gotten close to finishing. Much respect!
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Edited by AkikoKumimo: 4/23/2017 11:44:00 AMHaven't had any super difficult games to beat. Now to 100%, I would say Kingdom Hearts 2 Final Mix. Simply because that fight with lingering will is a BITCH.