5. Treehouse of Horror V
Originally Aired: October 30, 1994
Written by Greg Daniels, Dan McGrath, David X. Cohen, Bob Kushell
“Acchh!! I’m bad at this!”
In truth, any of the first six or seven Treehouses of Horror would probably rank as one of the show’s best episodes. I might even like IV a little better than V. But V has one thing the others don’t: Groundskeeper Willy. I’m sorry, but seeing the well intentioned Scotsman repeatedly axed in the back by a variety of characters is pure brilliance. Sure, a future world ruled by Ned Flanders is funny—ditto the idea of ‘The Shinning’ or the fact the Grandpa Simpson gave Homer time travelling advice on his wedding day. But c’mon. Nothing beats cold hearted, nonsensical murder for comedy gold.
4. And Maggie Makes Three Originally Aired: January 22, 1995 Written by Jennifer Crittenden
“Hey wait a minute. What are all these presents? It looks like you’re…showering…Marge with gifts. Hm…with little, tiny, baby-sized gifts. Well, I’ll be in the tub.”
This might not be one of the funniest episodes, but it’s hard not to feel some sympathy for Homer. He finally fulfills his dream of getting a minimum wage job at the bowling alley, only to be forced to give it up to support his new surprise, Maggie. Homer’s touching decision to put his family first and “Do it for her” is in such sharp contrast with the selfish jerk the character has evolved into that it almost makes me wish the show had ended right here.3. Cape Feare
Originally Aired: October 7, 1993
Written by Jon Vitti
“Yeaaaaagggrrrrrr”
That’s the sound of Sideshow Bob stepping on a rake. Like the Treehouse of Horror episodes, there are plenty of good Sideshow Bob episodes to choose from. This one wins because of the great parody of Cape Fear, Homer’s consistent ineptitude at seeing the severity of Bart’s crisis, and Kelsey Grammer’s delightful singing voice. At the time this episode came out I had a friend who was actually frightened by it, and I must say that the idea of a grown man trying to murder a ten year old boy could potentially be pretty freaky. Thankfully, great writing and a street full of rakes transforms the idea into something hilarious.
2. Lisa's Wedding
Originally Aired: March 19, 1995
Written by Greg Daniels
Homer: I just want you to know I’ve always been proud of you. You’re my greatest accomplishment and you did it all yourself. You’ve helped me understand my own wife better and taught me to be a better person. But you’re also my daughter, and I don’t think anybody could have had a better daughter than…Lisa: Dad you’re babbling.
Homer: See? You’re still helping me.
Growing up with the show, Lisa was always the character I related to the most. I wasn’t a troublemaker like Bart and thought too much to be like Homer; like me at that age, Lisa was thoughtful, good at school, and something of a loner. Many fans I've spoken with share my affinity for Lisa, and I get the feeling many of the shows writers do as well. This episode has great gags: the propensity of future robots (from the year 2010!) to malfunction and the absolutely incompetent take on history at the Springfield Renaissance Faire; it’s also great to see the future fates of some of our favorite Springfield residents, especially Milhouse. All of the jokes aside, however, it's Lisa's commitment to her family that makes this episode memorable.
Throughout the series, Lisa’s intellectualism has sometimes made it difficult for her to relate to her father. Here, Lisa gives up her fiance for Homer's sake, and despite how ridiculous these characters sometimes act, their humanity shines through during the last five minutes of this show. (This is the exact same sort of sensibility Greg Daniels would later bring to The Office.) I've seen this episode a hundred times, and it’s still hard to keep my eyes dry when I watch eight year old Lisa’s face light up with excitement at learning just how much she loves her dad.
1. Marge vs. The Monorail
Originally Aired: January 14, 1993
Written by Conan O'Brien
Marge: Homer, there's a man here who thinks he can help you.
Homer: Batman??
Marge: No, he's a scientist.
Homer: Batman's a scientist.
Marge: It's not Batman!
This was an easy call. There’s not much to say about this one that hasn’t already been said. If you haven't seen it, all I can feel for you is pity. From the moment Homer crashes through his car window until the last person falls to their death off the Escalator to Nowhere, there’s not a second in this episode that isn’t hilarious. Every single line is quotable. Almost sixteen years later, this is still the funniest thing I have ever seen on TV. No joke.
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