You know that feeling when you're about to do something moderately risky—maybe trying to fix a leaky faucet without calling a plumber or "investing" in a weird crypto coin—and that specific, high-pitched voice pops into your head? "What could possibly go wrong?" It’s the ultimate jinx. In the world of The Simpsons, that phrase isn't just a line of dialogue; it’s a death knell. It’s the verbal equivalent of a "Kick Me" sign pinned to the back of fate.
Honestly, it’s kind of wild how much mileage the show has gotten out of five simple words.
Most people associate the phrase with Sideshow Bob, the erudite, palm-tree-haired villain who just wanted to be a high-brow entertainer but ended up being a serial attempted murderer. When Bob says it, you know a crate of rakes is about to hit him in the face. But the phrase has a weird, sprawling history in Springfield that goes beyond just one character. It’s the unofficial motto of a town built on a tire fire.
The Origins of a Springfield Curse
If you look back at the golden era—roughly seasons 3 through 9—the writers were obsessed with the hubris of the average American. The Simpsons what could possibly go wrong became the shorthand for that specific brand of overconfidence. Take the classic episode "Itchy & Scratchy Land" from Season 6.
The family is headed to a high-tech theme park filled with animatronic robots. What’s the worst that could happen? Everything. The moment the phrase is uttered, or even implied by the park’s existence, the robots inevitably turn into killing machines. It’s a direct parody of Westworld (the original movie, long before the HBO show), but it works because Homer Simpson is the personification of the "what could possibly go wrong" mindset. He is a man who once ate a giant sub sandwich that was literally turning gray and grew a beard of bees just because he could.
✨ Don't miss: Cast of Absolutely Fabulous TV Show: Where They Are in 2026
But wait. There’s a specific character who basically owns this line.
Bubsy the Bobcat, the video game mascot, is often blamed for the phrase, but in the context of The Simpsons, it’s almost always a setup for a slapstick tragedy. In the episode "Cape Feare," often cited as one of the greatest half-hours of television ever produced, the tension between Bob’s sophisticated persona and the sheer entropy of the universe is the joke. He thinks he’s in a refined thriller; he’s actually in a cartoon where he’s going to step on nine rakes in a row.
Why This Specific Phrase Stuck
Why does it resonate? Why is it still a meme in 2026?
Because it’s relatable. We’ve all been there. You start a project with total confidence, ignore the warning signs, and then the metaphorical rake hits you in the bridge of the nose. The Simpsons didn't invent the phrase, but they perfected the timing of the fallout.
In the episode "The Itchy & Scratchy & Poochie Show," the writers poked fun at the "cool" new character trope. Poochie was meant to be the answer to declining ratings—a radical, surfing, rapping dog. He was the corporate version of "what could possibly go wrong." The answer, of course, was a total creative meltdown and a fan revolt. The show has always used this phrase to mock the idea that you can control chaos with a positive attitude or a marketing budget.
It’s also about the subversion of expectations.
Most sitcoms of the 80s and 90s were built on things working out in the end. The Simpsons flipped that. If someone says things will be fine, they absolutely won't be. The phrase acts as a trigger for the audience. It’s a "look out behind you" for people who like satire.
The Sideshow Bob Factor
We have to talk about Kelsey Grammer’s voice. The way he delivers the line—with a mix of condescension and misplaced intellectual superiority—is what makes it iconic. Bob represents the person who thinks they are too smart for failure.
- He plans a political takeover ("Sideshow Bob Roberts").
- He tries to frame Krusty the Clown.
- He attempts to blow up a television station.
In every instance, his own ego is the trap. The phrase the Simpsons what could possibly go wrong is basically the theme song for Bob’s life. He isn't just unlucky; he is cosmically punished for his arrogance.
✨ Don't miss: Why the Charlie and the Chocolate Factory book cover keeps changing (and which ones actually matter)
Beyond the Screen: The Meme Culture of Failure
Today, you see the phrase used in Reddit threads about failed DIY projects or on TikToks of people trying to do backflips off of moving vehicles. It has transitioned from a scripted line to a universal internet shorthand for "I am about to make a huge mistake."
The show’s "predictive" power often gets brought up here too. While people love to claim The Simpsons predicted everything from the presidency to the Super Bowl, the real "prediction" is the constant cycle of human error. We keep saying "what could possibly go wrong" because, as a species, we are remarkably bad at gauging risk.
Springfield is just a mirror of our own poorly planned decisions.
Whether it's Mr. Burns trying to block out the sun or Marge trying to "fix" the town by banning sugar, the result is always the same. The universe has a sense of humor, and it usually involves a giant boulder or a swarm of angry bees.
The Subtle Art of the Slapstick Setup
Comedy writers call this "the rule of three," but The Simpsons often pushed it to the rule of ten. The rake scene in "Cape Feare" wasn't supposed to be that long. Originally, it was a short gag. But the writers found that the longer it went on, the funnier it became. It moved past funny, into annoying, and then back into hilarious.
That’s the essence of the "what could possibly go wrong" energy. It’s the persistence of the failure. It’s not just that one thing goes wrong; it’s that the entire foundation of the plan was flawed from the start.
📖 Related: Why Do Jeremiah and Belly Break Up? The Messy Reality of That Motel Scene
Real-World Examples of the Springfield Curse
- The Monorail: A town gets a windfall of money and, instead of fixing the main street, they buy a literal "lemon" of a transit system because a guy in a fancy suit sang a song.
- The Canyonero: Buying a massive SUV that is "unexplained fires" waiting to happen just because it feels powerful.
- Homer’s Odyssey: Every time Homer takes a new job—NASA astronaut, pin monkey, beer smuggler—he enters with the same blind optimism.
The brilliance of the writing lies in the fact that we don't hate the characters for their stupidity. We recognize it. We’ve all bought the "Canyonero" in some form or another.
How to Avoid Your Own "Simpsons" Moment
If you want to avoid living out a "what could possibly go wrong" scenario in your own life, there are a few Springfield-inspired lessons you can actually use.
First, ignore the "Sunk Cost Fallacy." If you’re stepping on rakes, stop walking in that direction. Sideshow Bob’s biggest mistake was never the first rake; it was the eight that followed. In business and in life, we often double down on a bad idea because we’ve already invested time in it. Don't be Bob.
Second, listen to the Lisa in your life. Every "what could possibly go wrong" moment usually has a voice of reason (usually Lisa Simpson) pointing out exactly what will go wrong. We ignore those voices because they’re "boring" or "killjoys." But Lisa is usually right. If someone is telling you that building a house out of crackers is a bad idea, they aren't being a hater; they’re being a structural engineer.
Lastly, realize that "what could possibly go wrong" is a question, not a challenge. When you ask it, actually try to answer it. List the risks.
Moving Forward Without the Rakes
The legacy of the Simpsons what could possibly go wrong is really a lesson in humility. It reminds us that no matter how smart we think we are, or how well-planned our "Monorail" is, things can and will go sideways.
To apply this to your own life:
- Audit your optimism: Before starting a big project, do a "pre-mortem." Imagine it has already failed and ask why. This kills the "what could possibly go wrong" jinx before it starts.
- Value the skeptics: Surround yourself with people who aren't afraid to tell you your "Poochie" idea is terrible.
- Embrace the pivot: If the robots at your personal theme park start acting up, don't wait for them to turn into terminators. Shut it down and move on.
The show might be over thirty years old, but its grasp on human fallibility is timeless. We're all just one bad decision away from a rake to the face. The goal is to make sure that when it happens, at least the audience finds it funny.
Check your current projects for any "Springfield-style" red flags—overly complicated plans, ignoring the experts, or blatant overconfidence. If you find one, fix it now before the "what could possibly go wrong" becomes your reality.