Something Wicked This Way Comes (1983) ****
I'd been meaning to review this one for a few years now, as it's always been on my shortlist of "best PG horror movies" (along with the original Poltergeist and The Lady in White). I have a vivid memory of Octo yelling "OH NO!! WAHHH" while the two of us were watching this sometime in the late 80s. The particular scene had to do with a bunch of spiders crawling up out of the sheets while the kid character huddles in the corner of his bed, freaking out.
Now, having come back to this one 20 years later, I found it to be a little less terrifying that I remembered, but overall it has an atmosphere that matches what I remember appreciating so much. I think it would be stretching it a bit to call this a possible contender for the "A Christmas Story" of Halloween. It has that same nostalgia soaked vibe, though with perhaps less irony--but then, Halloween doesn't need irony the way that Christmas does. Lady in White might be another contender for that category--and JPX has already nominated the also excellent but R-rated Trick-r-Treat as his "go-to" Halloween flick.
Anyway, part of the cool nostalgia soaked atmosphere comes from the very stylized setting--the story is of a demonic carnival coming to a quaint little Ohio Valley town. The cinematography captures that sense of artificial perfection that you get when walking down Main Street in Disney World, which it of course borrows from the early masters of horror movies, the German expressionists.
Also part of the atmosphere is the mad fun chaos that accompanies any carnival--from the soul sucking carousel to the wish destroying hall of mirrors to the scary spider witch lady, the whole place is ripe for boys' fantasies and nightmares to come true.
The one flaw here is that some of the allegories do get a bit ham-fisted, and the boys' relationship fades to the background over the 2nd part of the film in favor of a morality tale. But there's still a cool central showdown between two class actors, Jason Robards and Jonathan Pryce. Pryce in particular is very cool as the demonic grandmaster of the carnival.