A "special" in the purest sense of the word, Witch's Night Out creates a world out of nothing that exists for about half an hour, then is gone forever. It's sharply written, with funny jokes, and animation that may be a bit crude, but is also stylish and unique. Now remastered on DVD!
The best of live action specials, to my mind. Judd Hirsch clearly has a ball as Count Dracula. The "History of Halloween" lesson is a BIT less horrifyingly inaccurate than most of them. There's a blooper reel hiding in storage someplace - I'd sure like to see it! Currently still just on VHS
This was perhaps THE Halloween special for my generation, and is surprisingly scary - the pirate ghosts at the end are legitimately spooky. This is always nice to see - so many cartoons are afraid to be the least bit scary. A DVD was released, making the expensive VHS tapes (which sometimes went for about 50 bucks) obsolete, but now even the DVD is rare!
Though the title alone makes it a "Halloween" cartoon (Halloween is never mentioned), this is a cool one. The music is catchy, the autumnal atmosphere is dreamy and inviting, and Hans Conried, one of the patron saints of Halloween specials, does as good a job as anyone could replacing Boris Karloff as the voice of the Grinch. They never do say what will happen when the Grinch shows up in town on Grinch Night, but you can bet your ass it ain't gonna be pretty. This one, at least, is easy to get on DVD.
It takes most of the special for Raggedy Ann and Andy to decide to get a boy a pumpkin, then they get him a pumpkin, and bring it to him. Indeed, this special really takes its own sweet time for anything to happen. But the sharp, funny dialogue and comedic touches help it rise above countless other boring Halloween cartoons where the creepy old lady turns out not to be so bad, after all. When you watch most specials as an adult, you marvel at how easily entertained you must have been as a kid. This one is far better than it sounds. Not on DVD, though VHS copies can be found.
The last of the major specials to continue airing regularly still holds up well, despite a distracting "World War I Flying Ace" subplot. The importance of Vince Guaraldi's note-perfect score cannot be overstated. DVD
This would probably rate higher if I'd grown up watching it - it's really much better than a few of the ones on this list. But you can't underestimate how big of a role nostalgia plays in how much we love these things. Now on instant video!
The first show I remember watching - in fact, I'm not sure I have any earlier memories of television at all than my memory of watching this at the house where we lived until I was 3. Just a compilation of earlier cartoons, but what great, spooky cartoons they are!
A made-for-video entry from a brief period when it seemed like they wanted to relaunch the Chipmunks as an all-Halloween franchise. Alvin and the Chipmunks Meet Frankenstein isn't much to write home about, but the Wolf Man movie was fantastic. Fairly funny, well written, and featuring plenty of that wonderful Halloween vibe that I love so much.
This animated adaptation of Ray Bradbury's novel gets a bit dull in parts, and the "history of Halloween" angle isn't entirely accurate, but it manages to make solid point about why we (and many other cultures through history) celebrate death and horror every year. It's got the best creepy house on the edge of town in the business, and a daring, haunting ending. Now on instant video!
Disney's own take on Legend of Sleepy Hollow is still probably the best (and most faithful) adaption of them all. This would be on top of the list if it wasn't disqualified for not being a true "special," just a movie that aired on Halloween a lot. I'm picky (perhaps "dorky" is a better word) about this kind of stuff.
These haven't really aged well, and "Bride" seems to be trying to cram a 13 episode TV series into a 90 minute movie, but the sheer number of letters I get from people who had nightmares about Mr. Boogedy speak for themselves. Only VHS rips were available for years, but they're now available as digital downloads in perfect quality!
Tim Burton's early short film pretty much lays out the template and style Burton would use in most of his subsequent movies when he became a major director. I can't wait for the new movie!