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The Triumvirate
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Megaman 1-6 - Dr. Wily. HE usually kicked my ass a bunch of times. But he was easy in 7 & 8.
Contra Shattered Soldier - The mission 6 boss. I can get through it's human form and frog form. But it's Squid and egg mode can be a real bitch.
All Time Hardest Boss
in General Discussion
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King DeeDeeDee in Kirby Air Ride(if you're not some weakling who goes for the Hydra machine). I got my ass kicked alot by him!