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For me, there's 2 bosses that come to mind where I genuinely had a tough time. The first, like a few others have already mentioned, is Malenia from Elden Ring who, and I'm not joking, took me damn near a day and a half, almost a whole weekend to beat on my first play-through (But damn was it satisfying when I finally beat her).
The second is the Lingering Will from Kingdom Hearts 2 Final Mix.
Holy shit. You wanna talk about a boss that really puts your skills to the test? This is the guy. To be fair, it is a secret post-game boss fight, so you can tell they fully intended this fight to be for anyone who feels they've mastered the combat system of KH2, because this guy will pull every trick in the book to try and put you down (And he will. Over and over and over...), but similar to Malenia's fight; once you beat him you really feel like you're on top of the world.
The second is the Lingering Will from Kingdom Hearts 2 Final Mix.
Holy shit. You wanna talk about a boss that really puts your skills to the test? This is the guy. To be fair, it is a secret post-game boss fight, so you can tell they fully intended this fight to be for anyone who feels they've mastered the combat system of KH2, because this guy will pull every trick in the book to try and put you down (And he will. Over and over and over...), but similar to Malenia's fight; once you beat him you really feel like you're on top of the world.