In a wonderful stunt, cable network FXX is airing a marathon run of all 552 episodes of iconic animated sitcom The Simpsons, in order. Since its premiere in 1989, the show has spent the last 25 years poking fun at American lives, families, culture, and, of course, businesses. We decided to take a look at the moguls, capitalists, and entrepreneurs who make Springfield’s economy hum. (Although we’d like to suggest that the businesspeople of Springfield eventually pick up a Fortune.) Presented below are 12 top business leaders from the show, and some of the highlights that make their careers shine.
C. Montgomery Burns
Owner, Springfield Nuclear Plant
Springfield’s oldest man, and its greediest, Burns is a thinly veiled parody of Citizen Kane’s title character Charles Foster Kane (himself a thinly veiled parody of William Randolph Hearst). He once literally tried taking candy from a baby, though that didn’t work out too well for the man whose nuclear plant has created a surplus of three-eyed fish in the town’s river. He also has an “excellent” fur wardrobe.
Creator of Malibu Stacy
Lovell is the genius behind Springfield’s favorite doll, Malibu Stacy, but then got pushed out of her own company after clashing with her fellow execs—oh, and funneling money to the Viet Cong. Lisa Simpson tracks her down so they can challenge female stereotypes with a new doll that channels “the wisdom of Gertrude Stein… and the down-to-earth good looks of Eleanor Roosevelt.” But in the end, the Lisa Lionheart doll is headed off by an aggressive move by the toy company to give Malibu Stacy a new hat.
Krusty the Clown
CEO, Krusty Korporation
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Krusty is more than the local clown and TV star Bart adores; he’s also a savvy marketer whose boundless licensing deals have made him rich. You might call him the Arnold Palmer of Springfield: Krusty has slapped his name and face onto everything from dolls to alarm clocks to lunch boxes to cereal. He does it all through his holding company Krusty Korporation. And the corporate clown is also a burger-slinger, with his fast food business Krusty Burger having been shut down by the health board more than once throughout the series. Like any great TV or film entrepreneur, Krusty also has his demons: he’s a compulsive gambler, repeatedly losing almost all the fortune he’s amassed from his brand.
Marge’s onetime prom date, and a terrible one at that, Ziff’s “busy hands” went on build a software company that turned him into a billionaire. No amount of money can buy Marge’s love, though, so Ziff spends his riches on such extravagant items as solid gold underpants, only to run afoul of the SEC and land in prison for misuse of his investors’ funds.
Owner, Springfield Kwik-E-Mart
Armed with a PhD in Computer Science but forced to man the counter at Kwik-E-Mart to help pay his student loans, Apu runs Springfield’s number one convenience store and Squishee distribution center. While foiling the juvenile exploits of Bart and crew as well as the occasional hold-up from resident bad guy Snake, Apu has applied his polite demeanor, and occasional snark, to providing strong customer service. In a smart policy, his automatic farewell of “Thank you, come again” both shows gratitude towards consumers while also extolling them to revisit the store, effectively setting up a channel for repeat customers.
Former CEO, Powell Motors
Homer’s older, half-brother is the CEO of successful automaker Powell Motors. At least, he is until he loses everything after allowing Homer to design a hideous car that bankrupts his company, forcing him to live as a hobo under a bridge. Still, “Unky Herb” needs only an idea, and a little seed money from Homer, to get rich again by inventing and marketing a machine that translates baby talk.
Owner, Moe’s Tavern
With some occasional exceptions (like zany plotlines involving romantic debacles or suicide attempts), Moe can always be found at Moe’s, where he is the owner, the bartender, and in many ways the comic relief, all in one. He’s the quintessential small-town businessman: he owns his one brick-and-mortar business and, although business is sometimes slow, he gets by. He’s also a businessperson who many in the town desperately rely on: Homer, Barney, Lenny and Carl all would be lost without the comforting, dark environment of Moe’s. As for how much revenue Moe pulls in from the bar each year, it’s hard to tell, but with weeks-old eggs sitting in a jar behind the counter, business can’t be booming.
Owner, The Leftorium
Although he’s better known for his religious fervor, his incessant friendliness, his needling catchphrases, and his dopey sons Rod and Todd, Homer’s neighbor is also the purveyor of the Leftorium, a store that sells all manner of products for lefties. The store is in the Springfield Mall; Flanders, formerly a pharma salesman, invests most of his life savings into the shop. In a 1991 episode gleefully titled “When Flanders Failed,” Homer temporarily puts the Leftorium out of business when he wishes on a wishbone for the shop to fail; after it does, his guilt leads him to spread the word about the store to local lefties (like fellow businesspeople Moe and Burns) and Flanders is able to reopen. Thank god-diddly-od!
Head of Globex Corporation in Cyprus Creek
Hank Scorpio poaches Homer from his job at the nuclear plant and promises great things for him in the Globex Corporation. Initially, he’s a great boss who schedules “fun runs” for his employees while handing out directions to the Hammock District. (Hint: it’s on Third.) Unfortunately, he’s also an evil genius who uses “the Doomsday Device” to blow up the Queensboro Bridge and demands a gold ransom from the United Nations. Homer doesn’t stick around to see how the evil plot turns out, but Scorpio still buys him an NFL team—but it’s the disappointing (to Homer, anyway) Denver Broncos.
Brand ambassador, Duff Beer
Branding matters. Over-the-top personalities can offer the perfect mix of spectacle and in-your-face attitude to get the attention of an unsuspecting consumer. And in the crowded field of alcoholic beverages, the party is even more important. Strapped with beer-laced utility belt, cape, spandex and sunglasses, Duff Man invokes the spirit of Springfield’s number one beverage: uninhibited party. All that Springfield drinkers need to remember is the easy catch phrase: “Oh Yeah!” (see also: the Kool-Aid Man) and accompanying party anthem of the same name by 80s Swiss band Yello. Duff Man may not be a businessman, but he’s a performer, a hustler, and the perfect corporate puppet—er, spokesman—to keep Duff Beer the top brand in Springfield.
CIO, Mapple Inc.
Like most Americans, Springfield residents can’t get enough of their mobile technology, and this is in part thanks to the innovative products from “Chief Imagination Officer” Steve Mobs, of Mapple (clearly a play on Apple visionary Steve Jobs), who sets up shop in the Springfield Mall selling MyPods, MyPhones, and offering help at the Brainiac Bar. But hyper-connectivity has its drawbacks, with Lisa running up a $1,200 MyTunes bill from music downloads and Homer becoming addicted to his MyPad (or as Marge calls it, his “adult Etch-a-Sketch”), resulting in deep depression when he accidentally drops it down a sewer drain.
Comic Book Guy
Owner, The Android’s Dungeon & Baseball Card Shop
“Worst. List. Ever!” That’s what Comic Book Guy would say about this article, we imagine. Then again, he doesn’t seem like the type to be found reading a Fortune.com story, or even any story online; he’s not a techie, but a different kind of geek. The purveyor of Bart and Millhouse’s favorite hang, salty though he may be, has had his fair share of nerd love affairs: Edna Krabappel, Principal Skinner’s mother, and, in a very recent 2014 episode, he finally finds his soulmate, a manga enthusiast named Kumiko. (Stan Lee marries them.) Still, love takes a backseat to Comic Book Guy’s real passion: the business. Brick-and-mortar strivers, take note.