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I'm not going to count shows aimed at adult audiences because that feels like cheating (that also includes not listing anime aimed at adults because that doesn't seem like the spirit of the question). Of shows aimed at and easily accessible during their run to children I'm going to say Courage The Cowardly Dog and Invader Zim.
Courage had insane creepy visuals in almost every episode.
Zim wasn't consistently freaky to the point of being notable in every episode, but the ones that were, they were really out there. The show was from the mind of the creator of the Johnny The Homicidal Maniac (which I read as a kid thanks to my interest in Invader Zim) and the show's darker elements are obviously reigned in just enough to get on TV.
I always always wanted all the JTHM comics as a teen. My parents said absolutely not! What do I have with my adult money? All the comics.
Jhonen apparently has hypnophobia so, that explains a lot.