Halloween in Charles Schulz's Peanuts frequently meant it was time for another run at the Great Pumpkin. This running gag, introduced in 1959, was sort of like Schulz's answer to Samuel Beckett's Waiting for Godot. Linus van Pelt spent every Halloween for almost 40 years waiting for the Great Pumpkin to arrive, and he never did.
The roots of the Great Pumpkin joke seem to lie in a comic strip from Oct. 23, 1959. Charlie Brown complains to Patty that he couldn't get a Halloween mask from the store... because they'd already moved on to selling all their Christmas decorations.
It's interesting to see this complaint in a comic strip from 67 years ago. We often assume that the aggressive commercialization of Christmas in particular has gotten worse in the 21st century, but it turns out it was still an issue when our grandparents were young.
It also helps bring the Great Pumpkin into context as a parody of that commercialization. As time went on and Schulz evolved the joke, the Great Pumpkin picked up enough of its own unique lore that it moved away from its origins. In its first appearance, it's more obviously a case of a little kid getting Halloween and Christmas confused courtesy of consumerism. By the '70s, it had become more of a commentary on religious culture and blind faith, with Linus occasionally going so far as to proselytize door-to-door on the Great Pumpkin’s behalf.
Every successive run at the Great Pumpkin gag saw Linus double down on it, sometimes roping other characters like Sally and Marcie into his pumpkin crusade.
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