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The Headless Specter was the disguise of Penrod Stillwall.
He wore the same exact clothes as the portrait of Jefferson Stillwall that hung in the parlor, but he had no head.
He had an eerie laugh as he chased people around.
Scooby-Doo, Where Are You!
The portrait itself was somehow rigged to periodically show the headless form as part of the spooky special effects Penrod set up (which included a floating candle) to scare potential thieves away, while he searched his broken-down home, looking for the hiding place of his great-great-great grandfather's secret treasure.
Scooby-Doo! Night of 100 Frights
The Headless Specter was a common villain at Mystic Manor.
- How could Penrod see if his head was inside his shirt?
- It's easy to imagine that Penrod told the story of the Headless Specter to be more menacing, but he apparently didn't tell anyone how Jefferson came to lose his head.
- With no head, the Headless Specter shouldn't be able to make a sound, although as a ghost (or at least as a pretend one) he could have the power to make sound.
- Whether he's standing or kneeling (most likely the former), the way the Headless Specter is positioned at the bottom of the chimney, there would've have to be a removable panel in the floor.
- Even if Penrod was just trying to scare people away, it didn't stop him from jumping on top of Scooby, Shaggy, and Velma, who he thought were hiding under a bed, unless he knew there was just pillows underneath the sheet. He also tried to knock Shaggy off his balloon.
- Clearly minutes have past between the time it took the gang to catch Penrod and Asa, yet the former managed to change into a sweater by the time of the latter's capture. Either this is an animation mistake or he was wearing one underneath his costume.
- When Penrod recieves the bag of treasure, he's wearing the gloves of the Headless Specter.