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Can't think of the hardest boss I've encountered, although some of the toughest bosses I've heard of come from Super Meat Boy, and the Souls series. I will tell of one of my most memorable bosses though; Bongo Bongo from OoT. First time I went against that beast on the N64, it was awesome. I was having trouble getting used to the patterns and switching between modes, but was super close to finishing him. It ended up taking two attempts to complete, but the reason it was so memorable was that I was so consumed by the fight it caused my heart to pump like crazy. That doesn't happen to me often while playing games. :)