The Simpsons has always had a somber undercurrent to its vision of the American experience. Even beyond the depressing elements of the core cast, the world of the series has a consistently sad air to it. Minor players that began as tragic background players (like Mr. Smithers, Ms. Krabappel, Milhouse, Nelson, Moe, and Selma) have all slowly been fleshed out and given plenty of room to be developed in the thirty-plus years The Simpsons has been on the air.

But in that time, even the minor C-list characters have been developed beyond what one would suspect. In fact, some have even been revealed to be quietly tragic in their own simple ways. It adds depth to the world of Springfield in surprising ways, and paints many of the major characters in new lights. Here are the saddest background characters from The Simpsons.

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SUPERINTENDENT CHALMERS

Superintendent Chalmers is typically held up as a straight man in the bizarre world of The Simpsons. He was introduced as a no-nonsense character for the ever-desperate Principal Skinner to bounce off of whenever Bart caused chaos. His straight man characteristics have waned and ebbed over the years (at times becoming just as silly as the rest of the world around him), but he's always been one of the few figures of authority in Springfield who seems to take their position within the town seriously. He even points out at various points that as Superintendent, he manages multiple schools throughout Springfield but ends up spending most of his time trying to put out metaphorical (and sometimes literal) fires at Springfield Elementary.

It's slowly been revealed in recent years just how sad the man's life has become. In Season 23's "Bart Stops to Smell the Roosevelts," Chalmers takes it upon himself to try and personally educate Bart. While taking him under his wing, Bart (and the audience) find out that Chalmers is a widower. But unlike Ned Flanders (who tried to find happiness again after the death of Maude with Edna Krabappel), Chalmers instead quietly accepted his loneliness. He's a single father to the snarky teenager Shauna, who constantly seems to be rebelling and arguing with her father just for the sake of causing trouble. Chalmers is also seen casually drinking in the early hours of the morning while taking care of children, in a much more somber, realistic portrayal of an alcoholic than the show usually tackles.

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BARNEY GUMBLE

Barney Gumble in The Simpsons smiling.

Almost the reverse of Chalmers, Barney Gumble was introduced early in The Simpsons. He was quickly established as Homer's longtime best friend and drinking buddy. But while Homer's alcoholism has been just one recurring element of the character, Barney was fully defined by his need for alcohol. While the early seasons often painted this as a joke, they also teased that it had destroyed all the potential he'd had as a young man. It's even revealed to be somewhat Homer's fault in a brief moment during season 4's "Mr. Plow," wherein a flashback shows Homer being the one to peer pressure Barney into drinking for the first time. All that makes Barney's decision to go sober in season 11's "Days of Wine and D'oh'ses" all the more potent, reaching his lowest point while at a party at Homer's house. Barney sees just how much of a wreck he's become and gives up drinking, but struggles to avoid temptation while still being with his friends.

It's around this time that Barney was somewhat phased out of the show. Lenny and Carl, as the two friends Homer could still be seen drinking with and also had been rising in prominence as Homer's work friends, replaced Barney in flashbacks and storylines. Whenever Homer needed a friend, it was usually those two while Barney got occasional references. It's almost like his attempts to go sober alienated him from his friends. His attempts to move on from drinking ended up failing as well, as season 14's "I'm Spelling As Fast As I Can" made a gag out of Lisa running past him on the street, drunkenly singing about how he's relapsed. He's been seen throughout the following seasons going back and forth, clearly experiencing a seriously dramatic and tragic story of a man struggling with his vices and gets no support from his best friend because he's too busy on a new adventure every week.

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DUFFMAN

Duffman is the corporate mascot for the Duff Brewing Company. He's a muscular and professional party hound who is never not selling his brand. As with any corporate mascot, there have actually been multiple actors who have been Duffman. But since the Duff Corporation doesn't want to "disillusion" Duffman's fans, they never recognize them as anything but Duffman. This makes it so that whoever is Duffman remains primarily nameless and unknown to the world. (Except in the case where Homer briefly took over the position in season 26's "Waiting For Duffman", which showed that passing the torch to a new Duffman was a more major event.) This makes the various depressing elements about Duffman all the sadder, as these men are left nameless while dealing with major personal strife.

One Duffman is shown to be so committed to the character that he can't separate his relationship with his ad family from a real one. Another mentions he has an estranged daughter that he's trying to reconnect with, who dropped out of college for reasons that are too sad to discuss in season 21's "To Surveil With Love." It's also been revealed that many of the men who have become Duffman have died at their post. It was even confirmed in season 12's "Jaws Wired Shut" when Lenny brought up that Duffman's death by liver disease had been covered by Newsweek. The new Duffman replied that "Duffman can never! Only the actors that play him!" One was shot in season 14's "The Great Louse Detective," and another seemed to die in a blimp accident in season 17's "Marge and Homer Turn a Couple Play." One even seemed to accidentally kill himself in season 22's "500 Keys" under the assumption that "I've heard drowning makes you feel like you're drunk." That last line takes on a new meaning in "Waiting For Duffman," where it's revealed that as Duffman, the actor is forbidden from ever actually drinking - which prevents them from enjoying the situations they are forced into every day of their lives.

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HANS MOLEMAN

Hans Moleman is perpetually one of the most put-upon characters in Springfield, which is really saying something given how poorly things go for pretty much everyone in the series. He's often seen in the most dangerous positions and jobs within the town of Springfield. It's even shown how fatal these jobs can be by having Moleman killed at various points, ranging from the mundane (car crashes) to the outright horrifying (having a drugged Mr. Burns stabbing him in the head with a power drill). But somehow, Moleman always comes back to life. That largely comes from the cartoonish nature of the series, although Moleman - like Kenny from South Park - seems to know on some level that things never go his way.

It's when the show decides to give him some level of realism that it becomes much more depressing. Although Moleman is usually shown to be elderly, season 4's "Duffless" hints that he's actually fairly young but has destroyed his body with substance abuse. Recent seasons have even revealed Moleman once had a more prominent role in the structure of Springfield. He was formerly the Mayor of the town, leading the town into an apparent economic success that defined the Springfield of thirty years earlier. But since then, he's been forgotten by the town in that way and relegated to the background. This is especially sad when one remembers that Moleman was eventually replaced by Mayor Quimby, who has proven comically corrupt and selfish.

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MARY SPUCKLER

Across the course of The Simpsons, Bart has gotten several brief love interests. This has included memorable guest appearances from Anne Hathaway, Sarah Michelle Gellar, Natalie Portman, Sarah Silverman, and Meryl Streep playing these one-off romantic interests. But one of them - Mary Spuckler, as played by Zooey Deschanel - actually has the distinction of getting a full character arc independent of the troublemaking Simpson. Mary appears across three episodes of the series, beginning with season 19's "Apocalypse Cow." Mary is introduced as one of the children of Cletus and Brandine. But unlike the rest of her family, she's portrayed as having charm, intelligence, and the will to be her own person. After she and Bart are almost married in her introduction, the two are revealed to have briefly continued their relationship before she disappeared. Bart follows her to New York in"Season 24's "Moonshine River," where Bart sacrifices his chance to be with her again to help keep her new destination secret from her family.

Mary ends up finding some success in the arts, but eventually returns to Springfield in "Love is a Many-Splintered Thing", also in the 24th season. She and Bart briefly try to rekindle their relationship, but Bart ends up pushing her away and ending up alone by the end of the episode. Mary is portrayed in a similar light to Lisa Simpson, a quietly brilliant and talented girl who lives in a world that doesn't appreciate her. Her own arc about self-discovery mirrors Bart's attempts (and ultimate failure) to live up to that. She's basically going through the same troubles as Lisa but from an even more desperate background. But unlike Lisa, Mary actually seems to succeed in escaping Springfield at the end of the episode, and in the process has to break Bart's heart. To make it even sadder, the coda for her last appearance is a shot from the future, which reveals Mary will end up being a surprisingly young widow.

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