Homer’s 15 Funniest Side Hustles on ‘The Simpsons’

Homer’s 15 Funniest Side Hustles on ‘The Simpsons’

Homer Simpson has had more life experience than almost any other being, living or dead, animated or real. Aside from working at the Springfield Nuclear Power Plant in Sector 7G, he’s had hundreds of part-time jobs, side hustles and get-rich-quick-gigs on The Simpsons, to varying success. The unifying factor — whether they thrived or failed miserably — has been that they were all hilarious. Here are 15 of the funniest…

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Mr. Plow

To score some extra cash during the harsh Springfield winter, Homer got a snowplow truck to shovel and move snow out of driveways and clear the roads. He even got a TV commercial out of it.

Grease Salesman

After he learns that he can sell grease for a profit, Homer recruits Bart to help him. Too bad that ACNE runs the grease and shovel racket.

Voice Actor

Due to his unique voice, Homer got the gig as Poochie, the new character for the Itchy & Scratchy cartoon. Ultimately, the character died on the way to his home planet, but not until after Homer got EXTREME!


Homer trains to be a bodyguard and ends up working for Mayor Quimby. It may not have been glamorous, but learning a knockout nerve pinch might have made it all worth it.

Food Critic

Homer gets a gig writing for the Springfield Shopper as a food critic with Lisa’s help. Sadly, his newfound authority on the town’s culinary scene is threatened when he can’t write a review on his own to save his life.

Prank Monkey

To experience his joy of pranking others while simultaneously humiliating an employee, Mr. Burns hires Homer to be his “prank monkey.” The money has to be good if Homer is willing to beg strangers for a diaper change.

Baseball Mascot

After entertaining the crowd as the new mascot for the Springfield Isotopes, “Dancing Homer,” Homer gets promoted to the big leagues as the new mascot for Capital City. Sadly, it doesn’t go over as well as in his hometown.

Fortune Cookie Writer

After claiming that a Springfield Chinese restaurant had mundane and uninspired fortunes in their fortune cookies, Homer gets a job writing those fortunes.


Thanks to possessing a thick cushioning fluid around his brain, Homer pursues a boxing career by absorbing blows and tiring out any Boxcar-level opponent for an easy knockout.

Personal Assistant to Alec Baldwin and Kim Basinger

After accidentally crashing into their private home, Homer becomes friends and personal assistant to then-couple Alec Baldwin and Kim Basinger, provided that he can keep their location a secret. Homer, being Homer, couldn’t keep his mouth shut, much to their and Ron Howard’s chagrin.


While the carnival is in town, Homer and Bart become carnies for some extra scratch.


In an effort to boost the TV ratings for space-shuttle launches, NASA hires Homer as an astronaut to get that everyman appeal. However, they weren’t prepared for a ruffled threat to be brought on board.

Door-to-Door Sugar Man

After stealing and shoveling 500 pounds of sugar into his car, Homer decides to make a quick buck as the neighborhood sugar salesman. It doesn’t add up to much cash, but he does get Principal Skinner grounded by his mother.

Sanitation Commissioner

After getting into a feud with his garbage men, Homer runs for sanitation commissioner and wins. It’s a short-lived victory as fulfilling all his insane campaign promises blows his entire annual budget within a month. Still, he got a catchy song (complete with U2 buttcracks) out of the ordeal.


After Springfield reinstates prohibition (since alcohol is the cause of and solution to all of life’s problems), Homer smuggles beer into the city as a bootlegger and “Beer Baron” for all the alcohol-enjoying citizens of Springfield. This causes Detective Rex Banner to come to Springfield, vowing to find and arrest this “Beer Baron.”

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