The Simpsons Wasted My Youth: Top 15 Episodes, Pt. 1 (15-6)

The Simpsons Wasted My Youth: Top 15 Episodes, Pt. 1 (15-6)

A while back, I was inspired by something that Evan Altman wrote called The Soundtrack to my Life. If you have some time and like Eminem, it's a great read. The part that spoke to me the most was his opening sentence: “When it comes to music, I'm not very well-versed.” This sums up how I feel about music. My personal list is probably a mismatch of different types of music; also a lot of Eminem, then more metal as I got older, then classic rock in my early 20's, and currently an odd mixture of Pink Floyd, Nelly, and Journey.


But that really isn't “The Soundtrack to my Life.” I like music, like any other human being; but it doesn't grab me. I don't feel motivated by music. I don't get inspiration directly from music. Music is just something that drowns out the rest of the noise to me. No, “The Soundtrack to my Life” is most definitely a combination of episodes of The Simpsons.

For this story, I originally started out trying to create a Top 10 Greatest Episodes list. After narrowing down to what was probably around 35 “surefire Top 10” episodes, I realized I needed to expand this a bit. With the help of trusted fellow Simpsons nerd @LarryByScott, I've compiled a Top 15 with an honorable mention list as well. So here is the first in a two-part series of best..Simpsons..episodes..everrr.

Honorable Mention

A Fish Called Selma (Season 7) - Selma marries Troy McClure, voiced by Phil Hartman, despite his fishy motives.

Hurricane Neddy (Season 8) - A hurricane destroys Ned Flanders' home and he ends up in the nut-house.

Last Temptation of Homer (Season 5) - Guest star Michelle Pfeiffer as Mindy, with whom Homer is smitten.

Homer the Smithers (Season 7) - Smithers goes on vacation, leaving Homer to care for Mr. Burns, who we learn has a living mother who had an affair with President Taft. “Taft, you old dog.”

Radioactive Man (Season 7) - Bart loses a role in the Radioactive Man movie to Milhouse, who hates the attention.

All-Time Greats (15-6)

15. Marge vs. the Monorail (Season 4) - Often regarded as one of the top episodes, but, frankly, is overrated. It has it's moments and features Phil Hartman as Lyle Lanley, the snake oil salesman pushing the monorail on the town of Springfield. Also has a short appearance by Leonard Nimoy as himself. The best moment is the iconic “Monorail” song (and Homer's screw-up at the end).

14. Treehouse of Horror V (Season 6) - Part of the yearly tradition of a trilogy of shorts parodying Halloween-esque stories, this episode is the best of the bunch. The skits include a Shining parody, Homer creating a time traveling toaster and messing with the past, and Principal Skinner and the teachers cooking and eating the children at school. There is a quick appearance by James Earl Jones voicing Maggie, and the best moment is Homer's “no tv and no beer make Homer...something something” rant.


13. E-I-E-I-Do'h! (Season 11) - Quite probably the last truly great episode of the series, this episode starts with Homer seeing a Zorro movie, using ketchup to make an “H” on Marge's dress, and eventually ending up back at the farm where he grew up. Using plutonium, he ends up mutating his crops and creating Tomacco, a crossbreed of tobacco and tomatoes. The best moment is a line from Ralph Wiggum, who after biting into the Tomacco, proclaims that “it tastes like grandma”.

12. Bart After Dark (Season 8) - The beginning of a run on Season 8 episodes appearing in this list, this one features Bart working after school at the local bordello to repay damages that he inflicted on the house. The existence of the house is brought to light and the townspeople turn on the lady that runs it, because of course they do. The whole thing ends in another classic Simpsons song (we put the SPRING in Springfield!). The best moment is Homer and Bart making “garbage angels” on the living room floor.

11. The Itchy and Scratchy and Poochie Show (Season 8) - Homer gets cast as the voice of Poochie, the new character added to the Itchy and Scratchy cartoon to create new interest in the show. Poochie is poorly visualized, and the character is a massive flop, much to the Homer's. The episode features Alex Rocco as Roger Meyers Jr. The best moment is the final appearance of Poochie, when he explains that he has to leave because his planet needs him (apparently he dies on his journey).

10. Homer's Enemy (Season 8) - Generally regarded as a classic, this episode is based around a new employee at the nuclear plant named Frank Grimes. Homer attempts to make friends with him, even nicknaming him "Grimey," but only annoys and infuriates Grimes. The tension simmers to a boil when Grimes attempts to set Homer up and expose his idiocy to the masses. It blows up in his face, and in a moment of temporary insanity, he electrocutes himself while grabbing high-voltage wires. The best moment comes at the end, when Reverend Lovejoy starts his eulogy “Frank Grimes, or 'Grimey', as he liked to be called.”

9. Homer at the Bat (Season 3) - This episode is great for several reasons, most notably the list of guest stars. Mr. Burns compiles a baseball team full of ringers, including Don Mattingly, Ken Griffey Jr., Daryl Strawberry, Ozzie Smith, and Roger Clemens, with the intention of winning a bet. The original players are moved to the bench, including Homer, the team's star. Things go awry for the team, as Griffey gets gigantism from a nerve tonic, Mattingly quits over an issue with his “sideburns,” and the only player they have left is Strawberry, who takes Homer's spot in right field. The best moment is Bart and Lisa heckling Strawberry, yelling “Darrrrrrrryl! Darrrrrrrryl!”, and the followup shot of a tear rolling down his cheek.


8. Last Exit to Springfield (Season 4) - When Mr. Burns wants to take away the dental plan at the power plant, Homer ends up the new union president and in negotiations with Burns. Under the impression that Homer is some kind of negotiating genius, Burns eventually folds to allowing the dental plan. Several great moments in this episode, including Homer's long thought process about Lisa needing braces, the “Big Book of British Smiles,” and the homage to Jack Nicholson as the Joker with Lisa in the dentist's chair.

7. Homer the Great (Season 6) - Feeling excluded from a secret society, Homer pushes his way into the Stonecutters only to find that he has a birthmark labeling him as the chosen leader. He quickly finds that it's less exciting being part of the group when everyone always allows him to win at cards, pool, and bowling. The end result is the forming of the ancient mystic society of...No Homers. The best moment is the Stonecutters' singing of “We Do” (which you can listen to here), and Homer's dragging of the Stone of Triumph. Amazing guest appearance by Patrick Stewart as the head Stonecutter.

6. A Star is Burns (Season 6) - The city of Springfield holds a film festival and Marge, who had the idea, invites Jay Sherman (of '90's super underrated cartoon comedy “The Critic”) to help judge the event. Sherman (voiced by Jon Lovitz) takes somewhat of a backseat after the first few minutes, considering the cartoon crossover. The plot is that Homer feels that Marge doesn't respect his intelligence, and wants to prove himself by voting on the film jury. Multiple classic Simpsons moments include the McBain action/comedy movie (“That was the joke”), Hans Moleman getting hit in the groin with the football, and people booing Mr. Burns (or maybe yelling Boo-urns?)

Check back again for the second part when I will unveil my top 5, with pictures, jokes, blurbs, and more Simpsons fun.


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  • Shari Bobbins has to be one of the all time tops, especially with "Half Assed Job, that's the American Way." Also included the Krusty Komedy Klassic at the Apollo Theater (KKK--that's not good).

    I still think the best Treehouse of Horrors was IX, where, besides the nuclear powered remote gets Bart and Lisa into the TV and they fall into Regis & Kathy Lee's soup, Kang impregnates Marge, and they all end up on Jerry Springer, where Homer and the Alien strangle Jerry. If that could only happen in real life.

    Besides the 3 or so reruns of the Super Bowl edition, where it was Buffalo vs NY, then voiced over Washington, etc. the only overtly censored one was the reruns of the "The Itchy and Scratchy and Poochie Show." While the Simpsons book documents that it included the line "and you'll never see him again," that was never in the reruns. Simpsons Wiki has 9 subsequent appearances, the most memorable being in the aforesaid Treehouse IX.

    I'll also put on my list "A Test Before Trying" (Season 25), which seemed an accurate portrayal of the Chicago School system. At the end, they said that Wilson school was supposed to be demolished instead of Springfield Elementary. I went to Wilson school, and it was demolished (in favor of O'Bannon school).

    Finally after my girlfriend said that her couple of removed twin cousins were Sheri and Teri, I asked if they were on The Simpsons.

  • In reply to jack:

    Hope you enjoyed part one. The Sherry Bobbins episode is one of my favorites and has my all time favorite moment (when she gets sucked into the air plane jet), but I just couldn't place it ahead of any of these. As I mentioned, when compiling my "top 10", I came up with about 35 that I felt were sure "top 10" episodes. It's a testament to what a great run the show had.

  • When I saw the end of "The Sopranos", I thought I wasted my time on following that show............I should have ended the show when Paulie and Christopher shot the Russian and got lost in the NJ woods and ending up eating packages of relish in an abandon van for the night.

  • In reply to CubsTalk:

    To quote comic book guy "....I've wasted my life."

  • In reply to CubsTalk:

    I thought you were going to get into the Fat Tony/Fit Tony/Fat Tony episode.

  • You almost lost me from the start with "inspired by something that Evan Altman wrote"...but a solid list so far. Hard to fully judge without seeing the rest. You also overlooked the historical education side of "Home At the Bat" in that it doubled the number of British Prime Minister's I could name.

  • In reply to North Side Irish:

    There's just too much to get it all! I also could've mentioned Mr. Burns' original starting 9, all of which were dead. Many for over 100 years. The final 5 are all deserving of top consideration, at least in my opinion.

  • fb_avatar
    In reply to North Side Irish:

    Grrrr...*shakes fist*

  • In reply to North Side Irish:

    On that one, it was somewhat ironic that Ken Griffey Jr. drank the stuff and got gigantism of the head, instead of Jose Canseco.

    That was also the second time Wade Boggs got pantsed at a bar, the other being Cheers.

  • In reply to jack:

    On the commentary for that episode, they mention that they had a whole different story for Canseco. However, when he came in with his wife to do his voice recording, she nixed the whole thing and insisted on approving any story involving him. That's why his story is that he's running into a burning building like some sort of hero.

  • In reply to Ryan Davis:

    Unless the story was that his squirrel had small nuts, it is hard to see what the problem would have been with her.

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