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50. The Mansion Family — A goofy ridiculous episode with no emotional resonance and just pure, dumb silliness. There's a monkey knife fighter named Furious George, and a million good jokes. It may be a shallow episode, but it's so funny it doesn't matter.
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49. The Old Man and the Key — There's a funny trip to Branson, Missouri, not for the first time in Simpsons history, and some really good stuff from Grampa. Also from Homer in relation to his father, but Homer is the best TV character ever.
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48. 24 Minutes — As a straight up, non-canonical parody of 24, this episode can get away with whatever it wants because of that fact. It could have been dumb and lazy, but it wasn't. Homer, at one point, pretends to be a woman whilst riding in a dumpster to "act natural." It works, and it's wonderful.
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47. The Grift of the Magi — This is a goofy Christmas episode based around a magical, maniacal new toy called Funzo. It's funny, and it has a very amusing play put on for the benefit of Mr. Burns. And also Gary Coleman is there.
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46. The Wife Aquatic — Homer and Bart find themselves on a fishing boat, and then the boat ends up in a storm. It's another installment with great jokes that carry the rest of the plot.
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45. Helter Shelter — This is a parody of desperate reality shows, and it also features Squiggy from Laverne and Shirley. There's some funny stuff at a hockey game, and some great moments when the Simpsons are living in their old timey house under old timey rules.
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44. The Girl Who Slept Too Little — A cemetery moves next door to the Simpsons, and Lisa, the rational one in the family, becomes scared. It's one of the rare opportunities for Lisa to act like a little kid (which she is), and that's a big part of what makes it work. Plus, Homer says "bullshit." Sure, it's bleeped out, but, in context, it's very funny.
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43. Guess Who's Coming to Criticize Dinner? — This is a great episode to reference when you want to make fun of Jimmy Fallon's proclivity to love every, single thing. Homer becomes a food critic, and, at first, the only thing he gives a bad review to is a slice of pizza he finds under the couch (it had a Hot Wheel on it). Then, he becomes overly mean. Either way, it's funny.
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42. I, (Annoyed Grunt)-bot — Homer, in a desperate attempt to prove he is handy to his son, builds a fighting robot, and then actually climbs inside the robot to do the fighting. It's a strong premise, and it's executed well. Bart also has the great line, upon finding out the truth, wherein he happily, proudly says, "You risked your life, even though you're the sole provider for a family of five!"
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41. Fat Man and Little Boy — Bart starts making novelty shirts, Homer builds a functioning miniature nuclear reactor, there's a Willy Wonka parody and Blu Blocker sunglasses. It's a good time.