A show like Seinfeld is far too absurd for audiences to get seriously attached to its characters, regardless of how relatable they might be. As such, watching them experience various kinds of miseries, almost all of which are their own fault, is considerably funnier than sad.
That being said, there have been several moments scattered across the series that can, at least in some ways, be interpreted as unfortunate, mournful, dark, or downright pitiful. The episodes that contain these moments aren't and never will be considered through these moments alone, but their emotional impact have remained fresh in viewers' minds for decades now.
10 The Alternate Side (Season 3, Episode 11)
Starting with the theft of Jerry's car, this episode carries over into a hilarious failed attempt at making a reservation for a rental. George also deals with car issues, except his are related to the apparently simple task of switching parked cars across the street.
Then there's Elaine, whose relationship with Owen March has gone from thrilling to dull, but right before she can end it, he experiences a stroke. It's not sad that she wants to dump him, but the fact that Elaine's only concern is her image paints a dismal picture.
9 The Invitations (Season 7, Episode 24)
The season 7 finale has George making rather objectionable choices for his upcoming wedding with Susan Ross. He clearly cannot bear the thought of getting married, so he brings out his cheapskate persona — insisting that their guests won't care about the quality of the wedding invitations.
George is right, but only because the invitations are never sent, having poisoned Susan to death (when she licks the envelope edges for sealing.) She is the most important character ever killed off on Seinfeld, a moment that should have been sad for George, who instead proceeds to call Marisa Tomei the first chance he gets.
8 The Face Painter (Season 6, Episode 23)
Elaine is quite annoyed that her boyfriend, David Puddy, is a maniac when it comes to the New Jersey Devils. Although his painted face doesn't cause too many problems at the game, Puddy pretty much traumatizes an innocent priest by running up to his car and screaming, "We're the Devils! We're the Devils! Hisssssssss."
Elaine obviously has to pick up the pieces, but then the priest reimagines her as the Virgin Mary. George endeavors to convey his declaration of love to Siena, but this backfires when she doesn't react. However, he's excited to discover that her left ear isn't as sharp as her right. George goes for it again, learning too late that she didn't miss the first instance.
7 The Subway (Season 3, Episode 13)
"The Subway" is problematic in a few ways, like when Jerry tells a naked man that he ought to be ashamed of his body. Pessimistic as it sounds, it's not as awful as what Kramer's, Elaine's, and George's storylines reveal — that New York City is a desolate nightmare where everybody is out for themselves.
George is robbed by someone he believes he's going to hook up with, Elaine is trapped in a crowded train without power, and Kramer is nearly mugged/murdered by a man trying to steal his gambling money.
6 The Fire (Season 5, Episode 20)
George is a lot of things, but brave is not of them. It's not like he doesn't know that he's a quitter; he doesn't even deny it most of the time. Except, of course, when he notices a minor kitchen fire in his girlfriend's home and wreaks more havoc than the actual flames.
The problem is not that Robin breaks up with him for his behavior, but that she thinks he's a coward (and only he's allowed to think that). George, somehow, worms his way back into her good graces, but his consequent lapse — screaming about a prop gun in public — lands him a well-deserved and conclusive breakup.
5 The Cheever Letters (Season 4, Episode 8)
When Susan Ross receives a box of items that survive the Ross cabin fire (courtesy of Kramer), she discovers a letter written by John Cheever, the famous American novelist known as the "Chekhov of the Suburbs." The letter reveals that Cheever and Susan's father were once in love and having an affair.
While the revelation was shocking to everyone who witnessed it and mentioned some embarrassing information, it was sad that Susan's father had to live a lie and that they couldn't be together and had to hide their love. Susan's father even said, "I loved him deeply, in a way you could never understand," showing just how serious the affair was.
4 The Handicap Spot (Season 4, Episode 22)
It's not possible to park in a handicap spot and expect no consequences if caught, as the fab four discover when Kramer (as usual) coaxes George into doing so. This seemingly simple act leads to a woman in a wheelchair getting injured, so the people in the area naturally take their fury out on George's (father's) car.
This isn't the dark part: that happens when Kramer decides that skimping on a new wheelchair is an acceptable idea, which turns out to be quite horrible when Lola is hurt again, and a lot more the second time.
3 The Gymnast (Season 6, Episode 6)
George is supposedly great with his partner's mothers, compared to his love interests themselves, but this talent takes a serious hit when he intentionally eats a chocolate éclair after it was tossed in the garbage, claiming that it was untouched by the rubbish surrounding it.
George's situation with Lindsay and her mother deteriorates further when she observes him cleaning a random man's car, and ultimately combusts when he exits their bathroom shirtless.
2 The Frogger (Season 9, Episode 18)
It's not really odd that a lot of the sadder moments in Seinfeld revolve around George Costanza — the man's neuroticism lends itself to an eternity of existential torment. He's terrified of everything: of success, of failure, of a happy life, of dying alone, but the thing that he's most proud of is the record high score he had on the arcade game, Frogger, in high school.
Having learned that nobody has beaten his score in nearly 20 years, George decides to purchase the machine. Everything seems like it's going well for him, but fate plays its hand against him once again: both Frogger and the last remaining shreds of his self-esteem are destroyed by a truck.
1 The Beard (Season 6, Episode 16)
Elaine's attempts at seducing a gay man into changing his "team" explode in her face, and justifiably so. Still, it's very uncomfortable that she thinks nothing wrong with the notion of forcing someone out of their established sexual orientation.
Elaine also goes a bit too far in this episode when she physically tears George's new toupee off his head and flings it out the window. It's not sad as much as it is deplorable behavior towards someone she calls her friend. Elaine's excuse is that the wig "made him look like an idiot" and "act like a jerk." Very sad behavior, indeed.
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