Come on, we all know who the creepiest boss is.
[spoiler]The final boss in Earthbound[/spoiler]
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He was creepy, but at this point he's just kinda meh :/
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Giygas -blam!-ing terrifies me as kid. Couldn't sleep after I saw him for a while. "I...feel..G..o..o..d".
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I had a Super Nintendo and never played Earthbound nor Chrono Trigger! I was too young to understand rpgs, jrpg is my fav genre since psone.