The Simpsons Bracket: Day 1 – Welcome to Insanity


By: Connor Lenahan

It goes without saying that The Simpsons is my favorite television show of all time. I have seen every single episode an absurd amount of times. I haven’t quite checked the math, but I believe that during my 20 year existence on this Earth I have spent somewhere around half a full calendar year just watching The Simpsons.

Now FXX is joining me in the obsessive watching. As you are reading this there is a marathon of every single Simpsons episode airing on FXX. That’s right, all 552, and the movie, in a row. For twelve days. It’s Christmas in August.

To coincide with this beautiful marathon, I have devised a marathon of my own. For the next nine days I will be putting up The Simpsons Bracket, a tournament to determine the best episode in series history. 512 enter, one leaves.

Now, obviously there are more than 512 episodes that have aired. Specifically there are 40 more. I made the executive decision that only the first 513 to air would count for the purposes of our bracket below. I was not interested in trying to fight between episodes in seasons 23-25 only to have them lose to “Last Exit To Springfield” in the first round.

I also did not make a typo above. The first 513 made the bracket. This is because I also decided to count “Who Shot Mr. Burns” as one hour-long episode as it follows one storyline. Outside of that it’s everything from seasons 1-23 and the beginning of season 24.

The bracket was randomly separated into eight regions for the sake of construction. This made for easier organization. Also, easier brackets to read. The eight regions are as follows:

Moe’s Tavern – 8/21

Springfield Nuclear Plant – 8/22

Springfield Elementary – 8/23

Lard Lad Donuts – 8/24

Krusty Burger – 8/25

Kwik-E-Mart – 8/26

Springfield Tire Fire – 8/27

And, The Leftorium. – 8/28

With The Finals coming on 8/29.

The winners from each of the eight brackets made it to the elite eight round of the tournament to determine a winner. I fully admit this is the least objective bracket in history. There’s a great chance that I eliminated your favorite episode/moment before it’s time. But therein lies the fun. The arguments this raised in my house caused so much laughter that it was deafening. It’s all an excuse to spend more time thinking about the greatest television show in history. Who says no to that?

One last thing to mention before we start: Seeding does not matter. At all. It was all a random number generator and an Excel sheet. Also, for many matchups I am just going to outright declare a winner when appropriate. I do not need to explain why “Marge vs. The Monorail” deserves to beat “Children of a Lesser Clod.” It’s just a better episode. No need to waste your time, or my time.

Without further ado, on today, the beginning to the Simpsons Marathon, I present The Simpsons Bracket.


Moe’s Tavern Region

 Round 1:

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Outright Victories:

“The War of the Simpsons” over “Today I Am a Clown,” “Bart Star” over “Homer and Lisa Exchange Cross Words,” “I Am Furious (Yellow)” over “Homer Scissorhands,” “Grade School Confidential” over “Lisa Goes Gaga,” ”Rosebud” over “New Kids on the Blecch,” “Marge Be Not Proud” over “The Wandering Juvie,” “Treehouse of Horror 5” over “Dumbbell Indemnity,” “Home Sweet Homediddly-Dum-Doodily” over “Smoke on the Daughter,” “Burns’ Heir” over “The Day of the Jackanapes,” “Angry Dad: The Movie” over “MyPods and Broomsticks,” “Lost Our Lisa” over “The President Wore Pearls,” “Old Money” over “She Used to Be My Girl,” “El Viaje Misterioso” over “Take My Life, Please,” “Mom & Pop Art” over “Simpson Tall Tales.”


Coin Flips:

“Goo Goo Gai Pan” over “The Fool Monty,” “Treehouse of Horror 10” over “Adventures in Baby-Getting,” “Beware My Cheating Bart” over “The Principal and the Pauper,” “Postcards from the Wedge” over “Bart Has Two Mommies,” “The Last of the Red Hat Mamas” over “The Blue and The Gray,” “Helter Shelter” over “The Monkey Suit.”



“Bart Gets Famous” over “Bart’s Friend Falls in Love” – I’m pretty sure I have used the line “You’ll have to speak up, I’m wearing a towel” at least once a week for the last seven years. Even weirder, I have also screamed “My boy’s a box, damn you, a box!” at the top of my lungs. That episode changed me man.

“Hellfish” over “Homie The Clown” – Before I get death threats, I think “Homie the Clown” is one of the funniest half hours of television I have ever watched. It’s incredible. That said, if you told me that they were going to make a feature length version of the “Hellfish” story I would get in line now. It’s one of the best stories the show has ever come up with.

“Colonel Homer” over “Lisa the Tree Hugger” – You know, if Homer doesn’t want to bunk with Lurleen then I’m totally game.

“The Secret War of Lisa Simpson” over “Alone Again, Natura-diddly” – Since I was a little kid I have wanted to pull off the same prank Bart does with the megaphones and only now am I approaching the financial ability to do it along with the insanity.

“Scenes from the Class Struggle in Springfield” over “Homer Loves Flanders” – “Just once in my life I’d like someone to call me sir without adding ‘you’re making a scene.’” Makes me die laughing every single time.

“You Only Move Twice” over “Homer at the Bat.” – This hurt. Really bad. I love both of these episodes dearly. In fact, on a test bracket a while ago I believe I had both in the final eight of the tournament. To have them in the first round is a severe betrayal on the behalf of the random number generator that helped seed these episodes. I chose “You Only Move Twice” in a razor thin victory because Hank Scorpio is the single greatest one time character the show has ever had. If he was the villain in the next real Bond movie then it would win 15 Oscars. I need a shower, this is evil.

“Brother from the Same Planet” over “Bart Carny” – I forgot how damn funny “Brother from the Same Planet” was until recently. I stand by Homer mistakenly calling Pepi “Pepsi” as one of the most genius moment the show has ever had.

“Homer’s Night Out” over “The Bob Next Door” – While I will openly admit that Sideshow Bob is my second favorite character behind Homer on the entire show, I can never watch “The Bob Next Door” without thinking it’s a bit too cartoonish by Simpsons standards. He cuts off his own face. Enough said.

“Lisa’s Rival” over “Homer vs Lisa and the 8th Commandment” – Yes, I have it wrong above. That’s because after I finished making this section of the bracket I remembered that I totally forgot about the subplot of Homer stealing the sugar, one of the finest points of comedy in history, and forgot to switch it. It’s incredible.

“Homer Badman” over “Homer Simpson in: ‘Kidney Trouble’” – I think it’s Homer’s anger that Marge won’t sit in a “hollowed out wheelchair” to store candy in that inspired me to wear a backpack on my own wheelchair entirely for the purpose of carrying copious amounts of candy.

“I Married Marge” over “Homer the Smithers” – As much as I love Homer decking Mr. Burns it’s hard to pick against the heartwarming story of Homer becoming a responsible husband and eventually father. It’s touching.

“Itchy & Scratchy Land” over “Bart vs. Australia” – By the time Homer begins chucking everything on his person at the robots in an effort to stop them – a banana, underwear, a camera (successfully) – I am in tears. Nothing about this could possiblay go wrong.


Round 2:

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Outright Victories:

“Bart Gets Famous” over “Goo Goo Gai Pan,” “Hellfish” over “The War of The Simpsons,” “Grade School Confidential” over “I Am Furious (Yellow),” “Marge Be Not Proud” over “Treehouse of Horror 10,” “Brother from the Same Planet” over “Homer’s Night Out,” “Burns’ Heir” over “The Last of the Red Hat Mamas,” “Lost Our Lisa” over “Angry Dad: The Movie,” “Old Money” over “Helter Shelter,” “Itchy & Scratchy Land” over “Mom & Pop Art.”


Coin Flips:

“Beware My Cheating Bart” over “Postcards from the Wedge.”



“The Secret War of Lisa Simpson” over “Colonel Homer” – Lisa’s longing for home is relatable to dizzying degrees. The ways she goes about fighting homesickness range from hilarious, calling Grandpa so he can ramble on, to heartbreaking – Marge singing “you are my sunshine.” Square in the feels.

“Scenes from the Class Struggle in Springfield” over “Bart Star” – There is an extremely decent chance that Marge is the greatest seamstress in the world. I realize how weird this is, but it’s otherworldly impressive she took one suit and changed it so many times successfully. I am aware this is a cartoon, but still.

“You Only Move Twice” over “Rosebud” – “Do you expect me to talk?” “I don’t expect anything from you, except to die and be a very cheap funeral.” Scorpio is the best.

“Treehouse of Horror 5” over “Home Sweet Homediddly-Dum-Doodily” – When I did a test run of this bracket months ago I actually had “Treehouse 5” in the final. This was almost entirely on the strength of the “Dad! Your hand is in the toaster!” scene. I love “Home Sweet Homediddly” but “Treehouse 5” is impossibly good.

“Homer Badman” over “Lisa’s Rival” – “Homer Badman” pulls off the greatest misdirection in the history of the show by beginning at candy expo and transforming into mistaken sexual harassment claim. Impressive is a gross understatement. Add in the fact it’s laugh out loud hilarious and you have a classic on your hands.

“El Viaje Misterioso” over “I Married Marge” – The matchup takes a beautiful tale of Homer and Marge’s marriage now and pits it against the beginning of their marriage. This goes far beyond my training as a furniture salesman. The decision falls to the Guatemalan Insanity Pepper because it takes the weirdest path of any episode to prove that Homer and Marge really are soul mates.


Round 3:

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Outright Victories:

“Marge Be Not Proud” over “Beware my Cheating Bart,” “Homer Badman” over “Old Money.”


“Hellfish” over “Bart Gets Famous” – “Hellfish” might be my favorite WWII movie of all time. It’s dark, hilarious, sweet, and just incredible. Plus it inspired the line that my brother Chase drops every time someone wakes him up from a nap: “…Santa?” I can’t knock it.

“The Secret War of Lisa Simpson” over “Scenes from the Class Struggle in Springfield” – I have a great respect for strength. Lisa fights through hazing and homesickness, just to name two obstacles, to make it through and complete her year at military school. It’s really Lisa at her strongest, and that’s a great thing.

“You Only Move Twice” over “Grade School Confidential” – Realistically you could justify putting “You Only Move Twice” deep in the tournament without once mentioning any scene that doesn’t feature Hank Scorpio or Homer. But everything in this is just perfect. It’s a machine.

“Treehouse 5” over “Brother from the Same Planet” – Here’s how good “Treehouse 5” is. It’s this deep in the tournament and I haven’t even mentioned “The Shinning” yet. It’s too good.

“Burns’ Heir” over “Lost Our Lisa” – Homer may not have a better moment as a father than when he drops the following knowledge on his kids: “Kids, you tried your best and you failed miserably. The lesson is never try.”

“El Viaje Misterioso” over “Itchy & Scratchy Land” – It is me, or is Johnny Cash a little too good as the Space Coyote? Plus Homer’s Chili hallucination is artistically gorgeous. As is the fact it happened on a “Chili Trip.”


Round 4:

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“Hellfish” over “The Secret War of Lisa Simpson” – Has anyone ever been happier about someone’s death than Grandpa about Asa Phelps? Also, the assassination attempt that is “as intricate and precise as a well-played game of chess” is amazing. Seriously, give me this as a movie.

“You Only Move Twice” over “Marge Be Not Proud” – “Marge Be Not Proud” is one of the most realistic stories I’ve ever seen. It actually makes me uncomfortable to watch as Marge’s anger is incredibly genuine. As powerful as it is, The Simpsons is rarely funnier than “You Only Move Twice” ever. When I watch The Simpsons I want comedy, so I’m going with Hank Scorpio.

“Treehouse 5” over “Burns’ Heir” – To knock it out of the park of a whole episode while telling three separate stories is no small feat. Obviously there have been plenty of Treehouses over the years, 23 make this bracket, but “Treehouse 5” is so clearly the best it’s unreal. It’s one of the funniest half hours of television ever, not just for The Simpsons.

“Homer Badman” over “El Viaje Misterioso” – Open offer: If anyone reading this can get me a Gummi Venus de Milo I will buy you a steak dinner. This is 100% legitimate. This episode is flawless.


Round 5:

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“You Only Move Twice” over “Hellfish” – Two of the most cinematic episodes ever made, yet it’s clear as the summer sky that “You Only Move Twice” moves on. Casual moments like Homer dejectedly kicking away a live grenade after quitting his job during an attack on Scorpio’s lair are too perfect for words.

“Treehouse 5” over “Homer Badman” – Two of the absolute best episodes of all time without question. I’m taking the side of “Treehouse 5” in a very close decision because a few of the lines/bits from the episode – Willie getting axed in the spine thrice, the toaster on the hand, “no TV and no beer make Homer something, something” – remain some of the funniest things I have ever heard just enough to bounce out the flawless “Homer Badman.”



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“You Only Move Twice” over “Treehouse 5” – Here’s the thing with Treehouse 5, it gives two A++ segments to open up the show, but the third act, “Nightmare Cafeteria” just isn’t as perfect as the first two. Amazing? Absolutely. But it dips just enough that “You Only Move Twice” can clip it. That episode is top to bottom flawless. Albert Brooks gives energy to the show whenever he appears that is impossible to match. Never does he fall into a character better than when he is Hank Scorpio. He isn’t on screen all that much, but when he is, he steals every microsecond. It reaches the final eight.

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Coming tomorrow, the Springfield Nuclear Power Plant region.