Last updated on October 31st, 2019
I’ve been a fan of The Simpsons from the absolute beginning when they started out as a cartoon short during the Tracey Ullman Show.
The characters have changed quite a bit over the years and none more so than Homer Simpson.
In early episodes, Homer was a hard-working father with good intentions who just never seemed to catch a break.
These days he’s little more than a buffoon bouncing from one comic adventure to the next.
But there is one character trait that Homer has managed to maintain through it all and that is his entrepreneurial side.
Time and time again Homer has started a side hustle to help support his family and get rich. Sure, Homer’s side hustle ideas pretty much always fail miserably (and are sometimes blatantly illegal), but at least he’s trying!
Here are my ten favorite Homer Simpson side hustle ideas:
After wrecking both his cars in a snow and alcohol induced accident, Homer ends up buying a truck with a plow attached.
Homer then starts his own snow plow business called Mr. Plow and even goes on public television with a homemade commercial and catchy jingle.
Call Mr. Plow, that’s my name. That name again is Mr. Plow.
His business is booming until best friend Barney decides he wants a piece of the action by starting his own business called Plow King.
A bitter competition drives them apart until Barney is trapped in an avalanche. Homer bravely saves him and the two promise to reconcile their differences and work together, with Homer saying, “When two best friends work together not even god himself can stop them!”
An angered God sarcastically says, “Oh no?” and promptly causes a heat wave that melts all the snow and effectively puts them both out of business.
Homer’s First Website
When Homer discovers his neighbor Ned Flanders has his own home-based internet business, he decides he wants a piece of the action too.
He launches his own internet company called Compu-Global-Hyper-Mega-Net. Before long Bill Gates shows up with a few of his goons, and despite the fact that he can’t even figure out what Homer’s business does, he decides to buy Homer out.
Unfortunately for Homer, Gates’ idea of “buying out” is having his goons destroy Homer’s office and snap his pencils, stating “I didn’t get rich writing a bunch of checks.”
Traveling Snake Oil Salesman
When Homer’s dad invents a tonic that promises to put the spark back in your sex life, the two of them go from town to town selling Simpson and Son’s Revitalizing Tonic.
All goes well at first but their success quickly fades and the tonic business comes to an abrupt end as they get into a big argument and Grampa tells Homer he was an accident.
When Homer finds an auto-dialer in a trash dumpster he uses it to annoy the population of Springfield with his Happy Dude telemarketing scam.
His scam, which offers the true meaning of happiness to anyone who will send him money, ends suddenly when Chief Wiggum kicks down his door and repeatedly shoots the auto-dialer that has been driving the entire town nuts.
Bart wins a radio contest and the prize is a real, live elephant. Of course elephants have quite an appetite and the Simpsons soon find themselves going broke trying to keep him fed.
In an attempt to raise money, Homer starts selling rides on the elephant but his outlandish prices ensure that this business venture is destined to fail.
Country Music Agent
After fighting with his wife, Homer wanders into a random bar and meets a waitress named Lurleen Lumpkin who sings a song on stage.
Homer connects with the song and before you know it he’s taking her to a recording studio to record a CD.
Her song is an instant hit and he becomes a country music star manager, Colonel Homer. Once he lands her a gig on a country western television series it seems like they’re poised to achieve greatness together.
But when Homer realizes that Lurleen wants to be more than just business partners, he is forced to end the relationship to protect his marriage.
Homer the Clown
Homer enrolls in a clown college and after graduating he begins impersonating Krusty the Klown at various events.
At first he loves the praise and freebies he receives but things take a bad turn when he is kidnapped by the Springfield Mafia, who mistake him for the real Krusty.
Eventually the real Krusty arrives and they both narrowly escape with their lives after performing a complex loop-de-loop trick on a tiny bicycle.
The Beer Baron
When a prohibition movement takes hold in Springfield the sale of alcohol is outlawed. But when Homer stumbles onto all the barrels of beer discarded by authorities, he sees an opportunity.
As the bootlegging Beer Baron, Homer secretly supplies beer to Moe’s Tavern (now disguised as a pet store).
When he runs out of beer he starts using stills to create his own brews and delivers them to Moe’s inside a bowling ball. Eventually the town decides it has had enough of prohibition and lifts the ban on alcohol, putting an end to Homer’s bootlegging venture.
After learning from Apu that he can sell grease for a profit, Homer begins frying up bacon at home so he can sell the leftover grease.
Realizing he’ll need much larger amounts of grease if he wants to earn enough to quit his job, he recruits Bart and the pair drive to Krusty Burger to try and steal the grease from the fryers.
Unfortunately, their big score is promptly stolen by a pair of goons from the Acne Grease and Shovel Company, who claim they control the grease business in Springfield.
Undeterred, they go for the mother-load…the fryers at Springfield Elementary. This time they are foiled by Groundskeeper Willie, who is relying on that grease to be his retirement plan.
Just check out the professional car wrapping he has done…
Selling Sugar Door to Door
Homer comes across a sugar truck that has crashed and spilled its load all over the road. He quickly hauls the sugar home to his backyard and decides he can get rich selling sugar door to door.
When Marge tries to discourage him by telling him the supermarket already sells bags of sugar for much less than he is charging and that their sugar isn’t full of rocks and glass, Homer argues “Those are minerals!” and continues his plan.
But he soon becomes obsessed with protecting his precious sugar from thieves. While he guards his supply, the sugar attracts bees from a local apiary.
The beekeepers offer Homer $2,000 to buy back their bees, but a sudden rainstorm washes it all away before the transaction can be completed.
Homer is left with no money and no sugar.
Mike Collins has been working in the financial industry since 2002 and is a self-proclaimed money nerd. He’s written for numerous personal finance websites and been featured on sites such as MarketWatch, Fortune, and Business Insider. Mike created Wealthy Turtle to give readers the tools and knowledge to manage their money like a rock star.