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30. I Won't Be Home for Christmas — This is the show's most recent Christmas episode. Homer is kicked out of the house, and finds himself wandering the city all night on Christmas Eve. It's a more somber episode than most, but it works really well. Homer's conversation with Ned is particularly excellent.
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29. Once Upon a Time in Springfield — This episode was billed as the 450th episode, and it aired after that 20th anniversary special hosted by Morgan Spurlock. Anne Hathaway returns as Princess Penelope, and it's an ideal role for her. It's also a great Krusty episode.
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28. Lisa Gets an "A" — There's a Crash Bandicoot ripoff in this episode, which should let you know it's one of the older episodes on the list. The ruse pulled over Lisa's eyes late in the episode is great, and so are Lisa's struggles with cheating. And, of course, there's the saga of Homer and Pinchy.
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27. Simple Simpson — Homer becomes a superhero who throws pies at people. There's just something really amazing about Pieman. And sure, the Dalai Lama flies, and that's a little ridiculous, but the rest of this episode is so good, and highly quotable.
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26. Skinner's Sense of Snow — All this episode really needed was a little "The Christmas That Almost Wasn't, but Then Was."
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25. Mayored to the Mob — This is a great episode for Mark Hamill, and it also has some great stuff for Mayor Quimby. And, of course, there's Homer as Quimby's new bodyguard.
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24. My Big Fat Geek Wedding — Skinner and Edna have plans to marry (plans set up in an earlier, not as great episode). This payoff is very good, though. It's a hilarious episode for Skinner, particularly due to his bachelor party, and also that song he sings to try and win Edna back.
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23. The Bart Wants What it Wants — Bart starts (sort of) dating Rainer Wolfcastle's daughter, voiced by Reese Witherspoon. However, this episode really takes off when Milhouse is introduced to the relationship dynamic. Any episode where Milhouse gets to spend this much time being desperate and pathetic is bound to be good. Plus, the Simpsons go to Canada!
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22. Behind the Laughter — An episode unlike any other episode, "Behind the Laughter" presupposes that The Simpsons is a show, but it was created by Homer and stars him and his family. It's a parody of Behind the Music, and an excellent one at that. They could only do something like this once, of course, but they knocked it out of the park.
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21. When You Dish Upon a Star — Homer becomes friends with Alec Baldwin and Kim Basinger. More importantly, he becomes friends with Ron Howard, who later steals Homer's idea for "The Terminizer: An Erotic Thriller." It's about a killer robot driving instructor who travels back in time... for some reason.