Homer Simpson's 16 Greatest Side Jobs

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Homer Simpson has been working at the Springfield Nuclear Power Plant for pretty much the entire run of The Simpsons. Sure, maybe he’s quit, or been fired every now and again. But in the end, the Power Plant is always there when the show needs it to be, which has become increasingly sparingly. However, Homer has always dreamt much bigger dreams, beyond simply being a cog in the world of nuclear power, and along the way he has taken on a job or two… or 50. Some have been more interesting, and more amusing, than others. Here are the 16 best side jobs Homer has ever taken up on The Simpsons.

1. Astronaut (“Deep Space Homer”)

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Homer is dangerously unqualified to be a nuclear safety inspector, but he was even more unqualified to be an astronaut. Of course, that was sort of the point, as NASA wanted an everyman to send into space—the kind of guy who yells at the President about Tang, and flushes toilets for fun. Homer’s adventures in space were high-stakes hilarious, with insect overlords, and ruffled potato chips. But in the end, a hero emerged: an inanimate carbon rod. In Rod We Trust.

2. Barbershop Quartet Singer (“Homer’s Barbershop Quartet”)

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Granted, Homer had this job before the events of The Simpsons began, but it still got its own flashback episode, where The Be Sharps reunited atop Moe’s for one last concert. Nobody in the group ever showed musical acumen again (aside from Barney), but for a little while, The Be Sharps were bigger than Jesus—and they have the album to show it.

3. Baseball Mascot (“Dancin’ Homer”)

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This was Homer’s first real venture into a job outside the nuclear plant, and also represented one of the Simpson family’s first ventures outside of Springfield. Homer becomes so beloved as a baseball mascot—a job he actually had acumen for and for which he also got some respect—that he is given the chance to do his schtick in the big leagues of Capital City. Alas, his down-home brand of mascot-ery doesn’t go over well with the big wigs in the big city. Homer also stops being a mascot pretty much right away because this is a sitcom, but he will always be able to look back fondly at his time standing atop the Springfield Isotopes dugout, dancing all the way.

4. Beer Baron (“Homer vs. the Eighteenth Amendment”)

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I know what you’re thinking. “Beer baron isn’t a job!” But the job is really that of a “bootlegger.” However, since he bootlegged beer, he became a baron during Springfield’s prohibition period. It is one of his most successful get-rich-quick schemes, and also one of his most illegal. It was a fun ride while it lasted, for the viewer, and for Homer.

5. Bodyguard (“Mayored to the Mob”)

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So enthused was Homer about smashing some nerds who were harassing Mark Hamill and Mayor Quimby, he ended up getting a bodyguard job. As is often the case with Homer’s newfound jobs, he got really into it, went too far, and then ended up losing interest just in time for the episode to end—which really worked out nicely for the show. Plus, Homer got to eat a watermelon version of Ann Landers.

6. Boxer (“The Homer They Fall”)

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Homer Simpson is far from athletic, but he managed to find some success as a boxer due to some extra fluid around his brain. Of course, “success” means he beat a bunch of hobos, and then Drederick Tatum almost killed him in the ring—and would have, if Moe hadn’t saved him. This was, perhaps, not Homer’s most successful job, although few people get the chance to headline a pay-per-view.

7. Carny (“Bart Carny”)

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We’ve all dreamed of a game where people throw ducks at balloons, and nothing is what it seems, right? Homer is no different. When Bart was forced into working as a carny, Homer insisted on tagging along. The job did not start off well for either of them, but they eventually got to briefly run the ring toss game for Spud and Cooder, the latter of whom was voiced by the late Jim Varney. Then, the two carnies ended up squatting in the Simpsons’ home, while the carnival was left in the distance. It remains one of Homer’s more notable jobs.

8. Food Critic (“Guess Who’s Coming to Criticize Dinner?”)

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On the surface, Homer as a food critic doesn’t seem to make sense, what with his general lack of education or writing skills. But Lisa provided the brains, and Homer brought the enthusiasm for food. When Homer did his own writing, it was all threatening references to the U.N., and “Screw Flanders.” It was Homer’s enthusiasm for pretty much everything he ate that made the gig especially memorable. Anytime somebody seems to be laying on the hyperbole, you can always trot out, “Nine thumbs up? What the hell is that!?”

9. Knock Off Krusty (“Homie the Clown”)

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While Homer got a lot out of being a fake Krusty, doing the things regular Krusty didn’t want to do, he was arguably worse at this job than anything else he’s done. In what other job, for example, did he almost beat a small immigrant man posing as a hamburger burglar to death, due to a misunderstanding? At least he learned the bike trick just in the nick of time. Homer may have failed, but he did so in one of the best episodes in the show’s history.

10. Monorail Conductor (“Marge vs. the Monorail”)

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Here’s a rare example of something going awry while Homer is on the clock, but he’s miraculously not responsible. He was just a patsy of the sinister huckster Lyle Langley—an unqualified monorail conductor in a poorly constructed monorail. Fortunately, with the help of a scientist who is not Batman and a donut, he is able to save Leonard Nimoy, and probably some other less important people. A great episode, and a reminder to always run a background check on anybody who tries to sell you a mass transit system.

11. Poochie (“The Itchy & Scratchy & Poochie Show”)

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Homer did everything that was asked of him when voicing the kung fu hippie from Gangster City that is Poochie. He was totally in our face. He was proactive. He sounded like a rockin’ dog. Of course, everybody hated Poochie, but, for once, that wasn’t Homer’s fault. Eventually, Poochie went back to his home planet, and Homer forgot to ask for any money. However, this adventure led to arguably the best episode in The Simpsons history, so it was worthwhile to viewers at least, even if we lost our beloved Roy when the episode ended.

12. Sanitation Commissioner (“Trash of the Titans”)

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For the 200th episode The Simpsons decided that Homer should take on the most exciting, glamorous job there is—sanitation commissioner. Thanks to crazy promises and assertions that Steve Martin’s Ray Patterson led children into his gingerbread house, Homer gets the job, and pretty much destroys the town (and manages to alienate U2). Also notable, this episode ends with the entire town of Springfield having to move down the road due to Homer’s negligence. Hey, at least there was a big musical number.

13. Sideshow Freak (“Homerpalooza”)

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In a way, this was Homer’s easiest job, because he simply had to be shot with cannonballs in the stomach, and hang out with The Smashing Pumpkins. This was a pretty sweet gig in the mid-90’s. Then, the cannonballs started to slowly kill him, and Homer had to decide between the glory of being a small attraction in a music festival’s freak show, or, you know, living. Homer decided on the latter, keeping “Homerpalooza” from being one of the more bizarre series finales in TV history. Because imagine if, say, the Mary Tyler Moore Show had ended with Lou Grant dying from a cannonball in the stomach. It would’ve been weird, right? Anyway, good times.

14. Snow Plow Driver (“Mr. Plow”)

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Who knew you could make a top-notch episode of television with a guy starting a snow plow business? Mr. Plow had a great jacket, a great commercial, and a great rival in the Plow King, aka Barney. Of course, Barney got Linda Ronstadt for his ad, which dwarfed anything Homer could do, but Mr. Plow remained the snow plow brand of the every man. That is, until God got mad and made all the snow disappear. It was kind of weird,

15. Sugar Salesman (“Lisa’s Rival”)

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This was, perhaps, the most circuitous of all of Homer’s jobs, but it also probably led to the best jokes from any of the side occupations Homer had. After finding a bunch of loose sugar on the road, Homer decided to fill his car up with it, and then tried to sell it door-to-door, even though it was not packaged. Of course, the best stuff all takes place in the Simpsons’ backyard. The big pile of sugar, Homer guarding it, the Beemobile, and so on. Genius, even if “unlicensed door-to-door bootlegged sugar salesman” isn’t something you usually see on TV.

16. Teacher (“Secrets of a Successful Marriage”)

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This was arguably Homer’s greatest failure, which, given his track record, is a major… accomplishment probably isn’t the right word, but let’s go with it—accomplishment. Sure, he managed to get the attention of his students in his marriage class, but only after he gave up teaching, and just started talking about Marge. Eventually, Marge was so put off by Homer’s candor, she kicked him out of the house, leaving him a man in tattered rags with a plant for a wife. The marriage was eventually saved, and Homer wisely decided that teaching wasn’t for him. He couldn’t afford to ruin anymore jackets, anyway.

Chris Morgan is an Internet gadabout who writes on a variety of topics and in a variety of mediums. If he had to select one thing to promote, however, it would be his ’90s blog/podcast, Existential Parachute Pants. (You can also follow him on Twitter.)

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