When younger, "The Headless Horseman of Halloween" was enjoyable but not one of my favourite 'The Scooby Doo Show' episodes. Really liked its creepiness, with a villain that is one of the freakiest of the series, but Scooby Dum didn't do much for me and did find him an annoying and unnecessary character when becoming a big fan of the show twenty plus years ago (will make a confession, still love the first three Scooby Doo incarnations and have never thought that 'The 13 Ghosts of Scooby Doo' was that bad).
Twenty plus years on, "The Headless Horseman of Halloween" is one of those episodes that got better and better over-time and actually is now one of my favourite 'The Scooby Doo Show' episodes. One of the episodes that was liked when younger and now love. Also have found that Scooby Dum has grown on me generally while still not always finding that he adds much, his most interesting appearance is "The Gruesome Game of the Gator Ghoul" though "Vampire Bats and Scaredy Cats" is his best overall episode.
Here in "The Headless Horseman of Halloween", Scooby Dum didn't come over as irritating and has amusing moments despite his laugh and his repetitive found a clue theme. To me though, my feelings of finding him not adding much to the plot have still not changed.
So much about the episode is great though. Really loved the mix of Scooby Doo and the timeless 'Sleepy Hollow' legend, they mix really well together and fit the Halloween occasion and atmosphere to perfection. It is one of the show's creepiest episodes too, and have always felt that. And it is not just the villain, who terrified me when younger and he still gives the creeps, but also the atmosphere. When he reappears with another character's head, that has to be one of the show's most shocking moments and when younger it actually freaked me out.
It is not just non-stop creepiness. The episode started off really well with the costume party, just loved those outfits. There are some lovely comic moments with Shaggy and Scooby as usual, it's goofiness personified but the visual gags and verbal jokes are very amusing and endearing. There's even a reference to horror legend Boris Karloff thrown in. The mystery is an interesting one with some clever clues that are not obvious, the identity of the perpetrator may not be a surprise (very few reveals in the show shocked with a few exceptions) but that didn't matter to me.
Animation may lack finesse, but the colours have lovely atmosphere and the backgrounds are lovingly detailed. The Headless Horseman looks great. The music fits well and the theme song is one of the franchise's best and most infectious. The voice acting is strong, Casey Kasem and Don Messick are still unsurpassed (though Matthew Lillard has been doing a very good job as Shaggy) and hearing Frank Welker so young is great, he has yet to show signs of being long in the tooth.
Overall, great episode. 9/10
