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90. Weekend at Burnsie's — Homer starts smoking pot! Thankfully, the episode isn't filled with a bunch of lazy marijuana jokes, which is more than a lot of TV shows can say. Sure, we have to listen to Phish briefly, but this episode has some great lines, and a good bit of farce at the end.
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89. Co-Dependents Day — Homer's drinking has long been the source of much humor on The Simpsons, but here, Marge gets to join in on the… well, fun doesn't seem like the right word. She ends up getting arrested for a DUI, even though Homer was, in fact, driving. It's a good Homer-Marge episode, and Marge drunk is a nice change of pace. Homer drunk is just business as usual, and business is good.
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88. The Man in the Blue Flannel Pants — A good guest star appearance from John Slattery in an episode that sort of parodies "Mad Men." On top of that, there's a great Bart and Lisa story in this one as well.
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87. Trilogy of Error — A homage to the (terrible) movie "Run, Lola Run," we see the same story from three different perspectives. It's very clever, and more importantly, it's funny.
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86. A Star is Torn — American Idol is another television institution that is no longer as beloved as it once was, and The Simpsons has done a couple of different American Idol episodes. But this is definitely the better one. That's because it's about Lisa and Homer, and Homer gets to be a stage parent. It's wonderful.
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85. My Mother the Carjacker — This is the second of the episodes featuring Homer's mom. It's also the second best of those episodes. But it's funny enough, and the whole bit that gets them into the mess with Homer's mom (involving newspaper typos) is really good.
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84. A Totally Fun Thing That Bart Will Never Do Again — If you are familiar with the David Foster Wallace story that gives this episode its title, then you probably know this episode takes place on a cruise. That's a good place for the Simpson family to hang out, especially with Bart's wacky hijinks.
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83. Insane Clown Poppy — Krusty finds out he's a dad, and he turns to the one man less capable of adequate fathering; Homer. Naturally, it's a funny combo, and Drew Barrymore is good as Krusty's daughter.
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82. Bart Stops to Smell the Roosevelts — An episode focusing on Superintendent Chalmers? You bet! Chalmers is a funny character, so angry and stern, and here he turns Bart (and some other rowdy kids) onto Teddy Roosevelt. It's a little odd, sure, but it's still a good episode.
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81. Jazzy and the Pussycats — Bart becomes a jazz drummer, and Lisa gets jealous. The episode has some funny arch bits that are strong, plus a cameo from George Meyer. Oh, and The White Stripes! But mostly George Meyer.