History YMMV / DarkSideOfTheRing

** The Road Warriors episode (mostly centered on Hawk's personal issues) would mark Animal's final appearance, as he would pass away four months later. The episode is already sad itself but also doubles HeartwarmingInHindsight (depending on one's beliefs) now that the two wrestling legends are now TogetherInDeath.

* UnexpectedCharacter: There were actually quite a few people surprised to see Luna Vachon's son show up, especially since her son is [[Series/HellsKitchen Hell's Kitchen]] fan-favorite, Van Hurd.

** The 1994 steroids trial against Wrestling/VinceMcMahon was the first known time the Wrestling/{{WWE}} chairman would be embroiled under public scrutiny. A year after the episode about the steroid trial aired, Vince and Wrestling/JohnLaurinaitis would find themselves under investigation over allegations of hush-money agreements and sexual harassment in the workplace, ultimately leading to Vince retiring from the company in disgrace. While Vince would return as an executive chairman in January 2023 in preparation for the company being sold to Endeavor (merging with the UFC in the process), it would be later reported that Endeavor CEO Ari Emanuel forbade Vince from having any creative say in the company, all but ensuring that [[OvershadowedByControversy his legacy remains forever tainted]] by the aforementioned hush money scandal.
*** In 2024, McMahon would be once again embroiled in another allegation of sexual misconduct, forcing him to resign his position as CEO of WWE and TKO.

** The 1994 steroids trial against Wrestling/VinceMcMahon was the first known time the Wrestling/{{WWE}} chairman would be embroiled under public scrutiny. A year after the episode about the steroid trial aired, Vince and Wrestling/JohnLaurinaitis would find themselves under investigation over allegations of hush-money agreements and sexual harassment in the workplace, ultimately leading to Vince retiring from the company disgrace. While Vince would return as an executive chairman in January 2023 in preparation for the company being sold to Endeavor (merging with the UFC in the process), it would be later reported that Endeavor CEO Ari Emanuel forbade Vince from having any creative say in the company, all but ensuring that [[OvershadowedByControversy his legacy remains forever tainted]] by the aforementioned hush money scandal.

** The 1994 steroids trial against Wrestling/VinceMcMahon was the first known time the Wrestling/{{WWE}} chairman would be embroiled under public scrutiny. A year after the episode about the steroid trial aired, Vince and Wrestling/JohnLaurinaitis would find themselves under investigation over allegations of hush-money agreements and sexual harrassment in the workplace, ultimately leading to Vince retiring from the company disgrace. While Vince would return as an executive chairman in January 2023 in preparation for the company being sold to Endeavor (merging with the UFC in the process), it would be later reported that Endeavor CEO Ari Emanuel forbade Vince from having any creative say in the company, all but ensuring that [[OvershadowedByControversy his legacy remains forever tainted]] by the aforementioned hush money scandal.

* UnexpectedCharacter: There were actually quite a few people to see Luna Vachon's son show up, especially since her son is [[Series/HellsKitchen Hell's Kitchen]] fan-favorite, Van Hurd.

** Wrestling/JacquesRougeau tricking the Wrestling/DynamiteKid into believing the former had mafia connections that would come after the latter if there was retaliation for the roll of quarters incident was very clever, but not particularly funny considering how much it frightened Kid and his family. Jacques' casual "oh yeah" remembrance of the incident and his glee in recounting how he pulled it off turns it into black comedy gold.

** The Road Warriors episode (mostly centered on Hawk's personal issues) would mark Animal's final appearance, as he would pass away four months later. The episode is already sad itself, but also doubles HeartwarmingInHindsight (depending on one's beliefs) now that the two wrestling legends are now TogetherInDeath.

* VindicatedByHistory: For over a decade, Dr. Martha Hart was one of the most despised people in wrestling due to her refusal to allow her husband Wrestling/OwenHart to be inducted into the Wrestling/WWEHallOfFame. However, after the episode that focused on Owen's death aired, which showed her point of view, many fans sympathized with her, some even agreeing that Owen should and would never be in the WWE Hall of Fame.[[note]]It helps that the episode aired during a time where negative opinion of WWE (or at least Wrestling/VinceMcMahon) was at an all-time high due to questionable decisions such as their business deal with the regime of Saudi Arabia and firing people in the middle of a [[UsefulNotes/COVID19Pandemic global pandemic]] despite setting profit records, and as such, at that point very few people were willing to give them the benefit of the doubt. It also helps that the episode showed that she has no issues with other pro wrestling companies or even pro wrestling in general (an assumption mistakenly held by some beforehand) as a result of Owen's death, she just has issues with the WWE, even giving Wrestling/AllEliteWrestling permission to hold a Owen Hart Cup honoring her late husband.[[/note]]

** '''Meta Example''': The 1994 Steroids Trial against Wrestling/VinceMcMahon was the known first time the Wrestling/{{WWE}} chairman would be embroiled under public scrutiny. A year after the Steroids Trial episode, Vince and Wrestling/JohnLaurinaitis would find themselves under investigation over allegations of hush-money agreements and sexual harrassment in the workplace, ultimately leading to Vince retiring in disgrace. Despite Vince having recently return as an executive chairman in January 2023, [[OvershadowedByControversy his legacy remains forever tainted]] by the aforementioned hush money scandal.

** Owen Hart's deadly fall occurred at an event called Over the Edge.

** The XPW episode has New Jack (filmed in early 2021) discussing his infamous fall off a scaffold and ends with him saying "So, I lived." The episode aired in October of 2021...five months after New Jack's death.
** The Road Warriors episode would mark Animal's final appearance, as he would pass away four months later. The episode is already sad itself, but also doubles HeartwarmingInHindsight now that the two wrestling legends are now TogetherInDeath.

* UnintentionallyUnsympathetic:
** Devon Nicholson does not come off as the victim he tries to portray himself. For one, the idea he was bladed against his will by Wrestling/AbdullahTheButcher is questioned as both men were familiar with each other and had wrestled several times, though his diagnosis of Hepatitis C was genuinely regretful. His attack on referee Lando Deltoro in World Class Pro Wrestling, where he jabbed him several times in the head with an iron spike, leaving several gouges that needed to be closed did him no favors either. His "Shit happens" attitude when discussing it and an arrest for domestic violence is the rotten cherry on top. The show itself deserves credit for not ignoring Nicholson's mistakes but he seems to think the viewers will take his side.
** Abdullah himself to some viewers, as his claims of illiteracy are unconfirmed and even surprise his longtime friends and supporters. The idea that he couldn't have someone read the process notice for the lawsuit and help him respond and avoid the default judgement, especially since he has a caretaker, is a bit hard to swallow. The fact that he didn't get checked for blood borne diseases despite nearly always bleeding in every match is also a very questionable choice.

* CrossesTheLineTwice: Wrestling/NewJack getting heat by thanking Creator/OJSimpson for killing two white people? Despicable. Doing it with a complete straight face without cracking up? Hilarious.

* MagnificentBastard: Wrestling/JacquesRougeau came off as this in the Wrestling/DynamiteKid episode. From getting his revenge on Tom by knocking 4 of his teeth out with a roll of quarters, to avoiding retaliation by ribbing him of all things, by passing Dino Bravo a piece of paper with a fake name to pass to Billington and convince him that TheMafia had a contract on him should he try to get revenge and knew where he lived, which legitimately scared Billington and his family and got him to sell his house and move away. Jacques recalls the events with amusement.

** '''Meta Example''': The 1994 Steroids Trial against Wrestling/VinceMcMahon was the known first time the Wrestling/{{WWE}} chairman would be embroiled under public scrutiny. A year after the Steroids Trial episode, Vince [[spoiler:and Wrestling/JohnLaurinaitis would find themselves under investigation over allegations of hush-money agreements and sexual harrassment in the workplace, ultimately leading to Vince retiring in disgrace]]. Despite Vince having recently return as an executive chairman in January 2023, [[spoiler:[[OvershadowedByControversy his legacy remains forever tainted]] by the aforementioned hush money scandal]].