Let's start with #5 - Elwood Crane aka The Headless Horseman.
This episode is one of my earliest memories of the show and is a corner stone as to my loving the show since childhood. Even though ol' Elwood tried to steal the family diamond and made the odd choice to use his own face for a disguise, he was a pretty crazy looking Horseman and landed at the # 5 spot. Plus this episode features Scooby-Dum (Scooby's cousin) and he always makes the show 14% better.
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