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Tootylicious said:
The two mantis in Jet Force Gemini were kinda tricky.
And Mizar, the final boss was definitely a tough one (but that's what final bosses should be like).

Oh and final encounter with Canary Mary in Banjo-Tooie!!

Altough not a boss, that canary was hell indeed. the game doesn't tell you that pressing the button fast = an auto loss. you have to find a medium speed  and only speed up a few meters before the finishing line, and even then she generally speeds up and wins. considering the course is really long, it's infuriating to start over.