15 Seinfeld Episodes That Have Aged Terribly

It's rare for a sitcom to remain relevant decades past its airing, but then again, it's also rare for a sitcom to be as great as "Seinfeld." The NBC series ran from 1989 to 1998, making television icons out of its four unlikable leads: stand-up comedian Jerry Seinfeld (with the real Jerry Seinfeld playing a fictionalized version of himself), neurotic George Costanza (Jason Alexander, playing a fictionalized version of series co-creator Larry David), shallow Elaine Benes (Julia Louis-Dreyfus), and wacky Cosmo Kramer (Michael Richards).

Despite the show's longevity and popularity, "Seinfeld" suffers from the same pitfall as a lot of '90s television: aging badly. Because the main cast are frequently sociopathic and callous, "Seinfeld" has quite a few episodes that are a lot more cringeworthy in 2025 than they were even in the 1990s. Even some of the best episodes of "Seinfeld" would never fly on modern-day TV, in spite of shows like "It's Always Sunny in Philadelphia" and David's own "Curb Your Enthusiasm" going much further in covering edgy material than their NBC predecessor. 

Read on to see our full list of the "Seinfeld" episodes that didn't age very well.

One of the most memorable supporting characters in "Seinfeld" is Wayne Knight's character Newman, Jerry's neighbor and arch-nemesis. Newman first appeared on-screen in the Season 3 episode "The Suicide," though the character ironically predated this appearance off-screen in an earlier episode, "The Revenge," which also touches on the topic of suicide. In the episode, Kramer attempts to dissuade Newman (originally voiced by Larry David, and later re-voiced by Knight in syndicated airings of the episode) from jumping off their shared apartment building. 

Though the episode is praised as one of the NBC show's earliest classic episodes, and even in retrospect is still favored by the cast, its blasé attitude towards Newman's attempted suicide (in spite of his surviving an initial fall) rivals the type of disdain Jerry would later show for the character in Season 3 and beyond. 

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Though Jerry and Elaine's romance didn't evolve past the show's early days, the third season of "Seinfeld" continued to play with the sexual dynamics of this heterosexual friend group with three men and one woman with "The Tape." The episode involves Elaine leaving a sexually suggestive voicemail on Jerry's answering machine as a prank, only for George to stumble upon it and develop an attraction to Elaine as a result. While it's a strong episode for future comedy legend Julia Louis-Dreyfus, it results in some pretty ugly behavior from its three male leads.

Particularly, this episode ages poorly given how, at the end of the episode, Jerry, George, and Kramer are all turned on by Elaine's voicemail, to her disgust. Additionally, the episode doesn't exactly translate to the modern day, given its focus on the physical answering machine, which is basically obsolete thanks to smartphones. Overall, "The Tape" somehow manages to be both misogynistic and dated at the same time. 

Whether you've seen "Seinfeld" or not, odds are you've likely heard the catchphrase, "These pretzels are making me thirsty." Originating in the Season 3 episode "The Alternate Side," many fans of the series probably don't remember that its context is in reference to one disgraced actor/filmmaker: Woody Allen. In the episode, Kramer snags a role in one of Allen's movies with one line of dialogue, and in the famous scene from the episode, he workshops how it should be delivered with Jerry, Elaine, and George.

While the mere mention of a true crime doc subject like Allen makes this episode incredibly dated, it also isn't even well-liked by the show's titular star. Jerry Seinfeld himself named it as his least favorite episode of the show, not for the "pretzels" line, but for one of the episode's subplots, in which Elaine wants to break up with her 66-year-old boyfriend until he has a stroke, making Elaine fear she can't leave him or she'll look heartless. 

"The Contest" did a lot for "Seinfeld"; in addition to being one of the most famous and acclaimed episodes of the series, it won Larry David an Emmy for writing, spiked the series' ratings, and coined the phrase "master of my domain." In the episode, Jerry, Elaine, George, and Kramer enter into a contest with one another regarding who can go the longest without pleasuring themselves. Its raciness was a remarkable feat for network television, but a huge plot point of the episode involves some pretty heinous behavior, even for the "Seinfeld" cast.

Namely, a huge wrench in this non-self-love-contest is the discovery of a naked woman through a window in the apartment across the street from Jerry's window. The four not only peep on this woman, but Kramer willingly loses the bet to the thought of her, and even goes out of his way to join in on her nudist ways while the other three watch. "Seinfeld" might've worked around network concerns by not saying the M-word in "The Contest," but they didn't get away with being horribly gross, even by 1992's standards.

Obviously, the main cast of characters in "Seinfeld" are all bad people, but in Season 4's "The Shoes," they stoop to the lowest of lows. During the meta plotline of Jerry and George working on a pilot for NBC, their deal is destroyed when NBC president Russell Dalrymple (played by guest star Bob Balaban) catches George ogling his 15-year-old daughter's cleavage. Rightfully so, because who wants to work with an actual pedophile? 

Unfortunately, as is often the case with "Seinfeld," Jerry and George come up with a scheme to get their way, and that scheme involves prostituting their friend. To prove that the sight of cleavage is unavoidable for men, they recruit Elaine to wear a dress showcasing her own cleavage. Dalrymple is then successfully seduced, and he gives Jerry and George their pilot deal back. It's quite a tactic to excuse pedophilia with blatant sexism, but at the very least, Elaine uses the situation to leverage Jerry and George for a role in their pilot. 

In some regards, "The Outing" was quite a revolutionary episode for TV in the '90s, depending on who you ask. Premiering during Season 4, the episode centers on Jerry doing an interview with an NYU journalism student (played by Paula Marshall) and mistakenly being labeled as gay due to his close friendship with George. Jerry and George subsequently try to correct the record, insisting that they're not gay — "not that there's anything wrong with that." 

Obviously, queer TV shows and LGBTQ+ representation have come a long way since this episode aired in 1993, but the fact that Jerry and George being labeled as gay creates panic among their friends and family is an incredibly outdated (albeit, sadly realistic for 1993) plotline. Additionally, the episode's other storylines aren't so politically correct either, as George also struggles to break up with a girlfriend out of fear of her becoming suicidal. 

Don't be fooled by the title of this "Seinfeld" episode from Season 5, because the reason why "The Masseuse" has aged poorly has nothing to do with its main storyline, in which Jerry persuades his girlfriend Jodi (played by guest star Jennifer Coolidge), a professional masseuse, to give him a massage. Instead, the trouble lies in the subplot involving Elaine. In the episode, Elaine is dating a new guy, Joel Rifkin (Anthony Cistaro), who happens to share a first and last name with a notorious early '90s serial killer.

One moment in the episode, which has aged like milk, sees Elaine suggesting new names for her boyfriend to go by instead of Joel Rifkin. One of the names she suggests is "O.J.," after O.J. Simpson. In case you're confused about the timeline, "The Masseuse" aired in November 1993, less than a year before Simpson was accused of murdering his ex-wife, Nicole Brown Simpson, and her friend Ron Goldman. So Elaine's Joel wouldn't have gotten much mileage out of changing his name to O.J., to say the least.

The respect that Native Americans get even today is still far below what they deserve, so it's not entirely surprising that during the fifth season of "Seinfeld" in 1993, there was a very insensitive plotline regarding Jerry Seinfeld's attempts to seduce a Native American woman. "The Cigar Store Indian" guest-stars Choctaw actress Kimberly Norris as Elaine's friend Winona. In the episode, Jerry presents Elaine with a titular wooden statue of a Native American as a gift in order to prove to Winona that he's generous, not knowing Winona's heritage. 

What's even worse about this inappropriate TV storyline that wouldn't fly today is that it was intentionally included by Seinfeld and Larry David in order to be politically incorrect, as the original script written by Tom Gammill and Max Pross, titled "The Moose Head," saw Jerry alternately offending an animal rights activist with a stuffed moose. Jerry's subsequent attempts to woo Winona see him making many more insensitive comments about her race, and yes, it's as cringe-worthy to rewatch as it sounds. 

If "The Cigar Store Indian" rubbed you the wrong way, wait until you hear about a Season 6 episode called "The Chinese Woman." The episode gets its title from its main plotline, in which Jerry mistakenly calls a woman named Donna Chang and asks her out on a date. Normally, this wouldn't be an issue, had Jerry not explained the reason why he asked her on the date: because he "loves Chinese women." Elaine appropriately calls him a racist for this, but Jerry defends himself by insisting that it can't be racist if he likes the race.

Beyond the fact that this is an elementary understanding of racial prejudice, Jerry is inevitably disappointed by Donna Chang after discovering she's not Asian and is, in fact, Caucasian, her name having been shortened from "Changstein." As if this isn't awkward enough, Jerry accuses her of manipulating him into thinking she was Chinese because she teaches acupuncture and enjoys Chinese food. Just... yikes.

If, and only if, you could argue that "The Outing" was not insensitive to the queer community, you at least would have to acknowledge that the Season 6 "Seinfeld" episode "The Beard" very much is. The episode guest-stars Robert Mailhouse as Robert, a friend of Elaine's who is a closeted gay man. After she agrees to see "Swan Lake" as his "beard" (meaning she's masquerading as his partner to avoid speculation on his sexuality), Elaine begins to fall for him unexpectedly and wonders if she can turn him straight.

Despite Jerry trying to warn Elaine that you can't "change teams," Elaine not only tries but succeeds in taking Robert to bed, only for him to come out of the experience still gay. Maybe this was a very funny concept for television audiences in 1995, but if this were to air on TV nowadays, it'd face a lot of criticism for having a very misguided view of how sexuality works. At the very least, we have lots of influential LGBTQ+ characters on TV to thank for that modern sensibility. 

No, we're not dinging this one because of Elaine's burning hatred for the titular 1997 Oscar winner starring Ralph Fiennes. (We kind of think she was right about that?) Instead, we can't help but cringe when we think back to Kramer's ill-fated attempt to acquire some "Cubans." 

When Kramer asks Jerry to bring him home some Cubans from Florida, Jerry naturally thinks he's referring to Cuban cigars. But he's shocked when three Cuban men show up at his parents' door. Kramer had the bright idea to bring them back to New York so they could roll Cuban-style cigars for him legally. (Because indentured servitude is a comedy gold mine, you see.) But Kramer is annoyed to discover the men are actually Dominicans, who lack the, um, "intoxicating aroma" that Cubans have. (Those are Kramer's words, to be clear, not ours.) The Dominicans end up rolling crepes at a restaurant before plotting a Communist revolution and (yeesh) hijacking Elaine's plane at gunpoint. "Seinfeld" was never a beacon of cultural sensitivity, but this is a real low point.  

The reason why this Season 9 episode, titled "The Merv Griffin Show," has aged poorly isn't because it makes heavy reference to the Emmy-winning late night talk show of the same name, but because of its subplot in which Jerry discovers that his new girlfriend, Celia (Julia Pennington), has a collection of vintage children's toys. After she refuses to let Jerry play with or even touch them, he does the obvious: He drugs her with pain relievers. 

This isn't an isolated incident for Jerry, either. After George and Elaine become interested in his scheme, they help him drug Celia with tryptophan and wine so they can spend longer and longer periods of time playing with Celia's toys like children. Elaine even goes far enough to steal gumballs from Celia's vintage Mickey Mouse gumball machine for her co-worker. It's one of the darkest things to happen in a "Seinfeld" episode... and that's saying a lot. 

By now, it seems obvious that whenever "Seinfeld" delves into race, the episode tends to age more poorly than others. This is true for one episode in the final season, "The Wizard," in which Elaine is convinced by Jerry that her boyfriend Darryl (Samuel Bliss Cooper) is Black. Normally, this would be an easy thing to tell, but Elaine's awkwardness around broaching the subject has her questioning if Darryl is, in fact, non-white, especially once he describes them as an interracial couple.

As it turns out, Darryl's not only white, but he believes they were an interracial couple because he had mistaken Elaine for a Hispanic woman. Although some could argue that the episode actually did a great job showcasing how uncomfortable white people can be when talking about race, it's a bit of a strange episode to watch in hindsight, given how poor the diversity on "Seinfeld" was, especially when it came to African Americans.

For the most part, "The Bookstore" is a decent episode of "Seinfeld" in which George is forced to buy a book after taking it to a bookstore bathroom, forcing him to shoplift the same book in order to return it "unmarked." However, the subplot involving Kramer is... pretty disgusting. In the episode, Kramer and Newman scheme to start a rickshaw business, but their wonderfully offensive idea is to get unhoused individuals to pull the rickshaws for them, because, as Kramer argues, "they're always walking around the city. Why not just strap something to them?"

It goes without saying that Kramer and Newman's scheme has incredible disrespect for unhoused people's own humanity; at the very least, it comes back to bite them in the end. After some hired unhoused people run off with Kramer's rickshaw, Kramer is forced to pull Newman up a hill to retrieve it. It's a rare moment where a "Seinfeld" character gets exactly the kind of punishment they deserve for their social transgressions. 

"Seinfeld" infamously had one of TV's worst series finales of all time, but at the very least, it's remembered more fondly than the penultimate episode, "The Puerto Rican Day." In a first for the series, "The Puerto Rican Day" was a joint effort from the entire Season 9 writing staff, and production-wise, it's unique for being an episode that takes place entirely in real-time, following Jerry, George, Elaine, and Kramer driving into Manhattan while navigating a Puerto Rican Day Parade that's created traffic across Manhattan.

The episode resulted in one of the most controversial moments in the entire run of "Seinfeld," where a flustered Kramer accidentally burns the flag of Puerto Rico and stomps on it to put the fire out. NBC issued an apology and subsequently pulled the episode from reruns until 2002, when it reinstated the episode into syndication with the flag-burning scene intact. Publications like Vulture still regard it as the worst episode of "Seinfeld"... and we don't disagree.