Treehouse of Horror XIX (Season 20; Nov. 2, 2008)
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Intro: In the 2008 election, Homer uses an electronic voting machine to cast his vote for Barack Obama, but the machine registers it as a vote for John McCain. He keeps trying to vote for Obama, and finally realizes the machine is rigged. Then it kills him. (Which, IMO, is still not as scary as the 2016 or 2020 elections.)
Untitled Robot Parody: In a parody of Transformers, it's Christmas and Bart buys Lisa a last minute gift of a transforming toy car. And um... soon there are transforming robots all over town, fighting each other and wrecking everything.
How to Get Ahead in Dead-Vertising: The opening of this segment is a spoof of the opening of Mad Men, which I enjoyed, despite not being a fan of that show. Then Homer accidentally kills Krusty the Clown, and some advertisers pay him to kill other celebrities so they can use their images in ads for free. Then a bunch of dead people in Celebrity Heaven, including people who've been dead a long time, so Homer couldn't have killed them, all decide to go to Earth and kill Homer and everyone around him. I didn't care very much for the segment.
It's the Grand Pumpkin, Milhouse: In a parody of It's the Great Pumpkin, Charlie Brown, Milhouse waits for a mythical "Grand Pumpkin" while all the other kids go trick-or-treating and then to a Halloween party. It's a pretty straightforward adaptation of the classic special, until the Grand Pumpkin comes to life and seeks revenge for all the pumpkin-carving and cooking, and whatnot. Then it gets pretty horrific. If I recall, this segment was pretty well-hyped before it originally aired, and I'd say it was worth it. It's definitely the best part of this year's episode. (It's mostly responsible for the rating I gave the episode; the other segments I'd definitely rate lower.)