With critics and audiences hailing the series as Fielder’s most brilliant and demented experiment yet after only two episodes, this writer was inspired to go back and revisit the comedian’s previous escapades on Nathan For You, which is currently streaming in its entirety alongside The Rehearsal on HBO Max. In order to maximize the amount of discomfort I can pay forward to others, I put together a plan of my own: to assemble 19 of Nathan for You‘s most cringeworthy episodes and rank them in terms of pure, unadulterated cringe factor. 

Cringiest moment: Nathan attempts to negotiate with someone’s mother for the amount of her body parts that he is allowed to burn into ash.

In one of the highlights of Nathan for You‘s fourth and final season, Nathan sets his sights on the repetitive nature of the talk show circuit by attempting to orchestrate “the perfect anecdote,” but in his decision to ensure every aspect of the story was truthful, the performer mines some prime cringe content, though the meta undertones of the episode prevent it from reaching its true cringe potential.

Cringiest moment: Nathan reveals his duties as the “human resources” department of Dumb Starbucks.

In the most infamous episode of Nathan for You, Nathan attempts to help a struggling coffee shop by utilizing parody law to rebrand itself as “Dumb Starbucks.” The episode, which garnered the attention of national news organizations, opens the floodgates for myriad cringe moments, from Nathan getting into a scuffle with a lawyer to his performances of sophomoric parody songs, though these moments are ultimately tame compared to the more egregious cringe elsewhere in the series.

Cringiest moment: Nathan attempts to woo the significant other of one of his “doubles.”

Private investigator Brian Wolfe has been a constant source of cringe moments throughout Nathan for You‘s 30+ episodes, and his debut appearance on the show definitely does not disappoint on that front, especially as Nathan decides to antagonize both Wolfe and the men he hired to portray him to mislead Wolfe. Unfortunately, Wolfe’s cringiest moments would have to wait for later in the series when his pornographic past comes to light, and ultimately, the disappointing second half of this episode definitely costs it some valuable cringe cred.

Cringiest moment: Nathan attempts to learn more about a prospective suitor by not-so-subtly asking him about his views on women.

Nathan for You has a great track record when it comes to cringe, but one that really takes the cake would be the “Dating Website” segment from this episode. While “Party Planner” is certainly uncomfortable at points, particularly when the Bill Gates impersonator takes the spotlight, “Dating Website” is among the series’ most unbearably cringey segments, from Nathan’s awkward “rescue phrase” to witnessing his unbelievable plan in action, noble intentions be damned.

Cringiest moment: Nathan attempts to charm an unwitting Best Buy employee on another fake dating show while posing as a Hot Topic employee.

“Electronics Store” might be, second-for-second, the funniest episode of Nathan for You, from Nathan’s improbable plan to the many speed bumps he encounters to the scene with the psychologist, which may just be the single biggest moment of gut-busting hilarity the show had to offer. But this bad boy ranks so high on the cringe list thanks to Nathan’s desperate attempt to source former Best Buy employees for a class action lawsuit, especially when he turns back to old (and supremely cringey) tricks, both literally and figuratively.

Cringiest moment: The parents decide to watch the carnal acts in progress during Nathan’s genuinely upsetting experiment.

One legitimately jaw-dropping episode of Nathan for You also includes a seismic level of cringe in its opening segment, in which Nathan devises a plan to make hotels safer for parents to engage in sexual acts while providing a sensory deprivation chamber for their children in the same room. While the experiment shockingly works, despite the best and loudest efforts of multiple porn stars, the scene acts as cringe run wild. The cringe level only rises from there when Nathan attempts to help a travel agency provide their elderly customers with affordable end-of-life services, including a side-splitting attempt to cremate an anatomically correct human body (made out of pizza dough) in a pizza oven.

Cringiest moment: Nathan gets a preview of a caricature artist’s “edgy” new illustrations.

“Gas Station” remains one of Nathan for You‘s most notorious segments, and its cringe level is notable especially as the extent of the rebate requirements are revealed and participants reveal strange and awful secrets on-camera, but the reason this episode is so undeniably high on this list is all thanks to “Caricature Artist,” in which Nathan guides a caricature artist to a surprisingly amount of success by rebranding him as the “king of sting” and encouraging him to offend every customer possible.

Cringiest moment: Bill makes an incredibly uncomfortable phone call.

In the only feature-length episode of Nathan for You, Nathan goes into full-on documentary mode to help the series’ resident Bill Gates impersonator with finding his long-lost love while simultaneously reckoning with his own “Lonely Nathan” subplot once and for all. Yet, when it becomes apparent that the impersonator at the center of the episode may not have been entirely forthright about his love story, the cringe comes in like a rising tide, threatening to sweep us all into its gut-punching current.

Cringiest moment: Nathan makes an agonizingly inappropriate request from his stunt driver.

Not all Nathan for You episodes are cringey from start-to-finish, but occasionally, small moments pack a wallop, as seen in the “Nail Salon” segment, in which Nathan interviews a professional stunt driver of whom he decides to make a request, which turns around on him very quickly; in fact, the delivery of Nathan’s reaction may be, arguably, the show’s most gasp-inducing moment.

Cringiest moment: Nathan goes on a date while in full makeup as his test subject.

“The Hero” is among the cringiest half-hours of television ever produced, with Nathan going above-and-beyond the call of duty to help a hapless stranger improve their life as a tight-rope walking “hero.” The maniacal extent to which Nathan goes to pull this off, from having his subject unwittingly undergo a face-scan to donning a mask of him to a date to interacting with the subject’s grandparents from a distance utilizing pre-recorded audio files, is guaranteed to make your bones want to bust out of your skin and run out of your living room.

Cringiest moment: Nathan attempts to bond with a customer’s boyfriend over a discussion about preferred sexual positions.

Nathan for You delivers a one-two punch of cringe with this phenomenal episode, which comes out of the gate with a bizarre and hilariously complicated scheme to make horseback riding safe for the morbidly obese. Just when you think the episode hits its nadir of cringe, the second segment, “Man Zone,” just shatters your expectations and guarantees all viewers will at least try to find a way to sink deeper into their seats. But even with all of the cringe you’ve already consumed, nothing can really prepare you for the all-encompassing cringe of the secret third segment of this episode, in which Nathan decides to start his own clothing company with a shocking motivation that is simply wrong to spoil.

Cringiest moment: Nathan pursues a line of questioning with guest host Anthony Napoli regarding the Holocaust.

Nathan for You cooked up an extra special recipe for cringe with “Nathan for You: A Celebration,” an extended episode that follows up on the majority of businesses and figures from throughout the first three seasons of the show, including Brian Wolfe, “The Ghost Realtor” Sue Stanford, and Corey Calderwood. The episode is chalk full of cringe, and while some get awfully close at taking the cake, including a hair-raising conversation in which Nathan asks a psychic medium about who really killed Nicole Brown Simpson, a volcano of cringe erupts upon the audience immediately after Nathan’s post-script on his Summit Ice clothing line.

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