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In terms of total time since I first played the game to finally beating it, probably Cave Story's Ballos fight for me. I had a fan made port of the game for the PSP back in '06 ish, struggled a lot to get the regular ending, found out about the true ending, and couldn't ever beat the Last Cave (Hidden), much less gauntlet of challenges beyond it. I think at the most I had seen that there was a secret area beyond the "final boss" for the true ending and the fan name for it, but never been. I might have once gotten to it but I know for certain I never ever beat it or the true final boss.
At some point around about 2018 ish I think I saw that they had a rerelease for the game on the Switch titled Cave Story+, where I fell in love with the game all over again and finally played it to its true completion. I still have all of the screenshots and videos I took during my first completion of that boss fight. I think since then I have beaten it on Hard Mode, but only ever on the Switch version with Co-op mode which allows you to double your damage output being that you have 2 players, so it'll be interesting trying to go back and complete it again soon without almost any Health pickups at all.