* AccidentalInnuendo: Spenny giving his goat a bath: "His big ballsack. Let's get it all clean... Yeah! He likes that!"
* {{Anvilicious}}: PlayedForLaughs. In every episode, Spenny tries too hard to teach the audience an important lesson from this scheme. Sometimes it was pretty obnoxious, like in the homeless episode how he commented on how he now realizes what it's like to be truly homeless after..... 15 minutes of sitting on a park bench on a sunny afternoon.
* BigLippedAlligatorMoment: In the middle of "Who's the better jew?" Kenny dons a Hitler costume, dubs himself "Adolf Shitler" and performs a soft love-ballad music video entitled "Where The Butterflies Flow."
* BrokenBase: How much of the show is real and how much is scripted is a major source of debate. Kenny himself has claimed that 100% of it is authentic, but fans have been able to pinpoint inconsistencies in some episodes that contradict his statement, such as Spenny's arms suddenly appearing untied in "First One to Use Their Arms Loses".
* CrazyIsCool: Kenny. He's even referred to by the Drill Sargent in the "Who's A Better Soldier" episode as "crazier than shit".
* CrossesTheLineTwice:
** Kenny's brand of comedy often involves doing things that are deliberately offensive, but so exaggeratedly so that the viewer can't help but be amused by him. The most blatant example is in "Who Can Put On The Best Play", where he writes and performs a one-man show about a Jewish prisoner enjoying the Holocaust. The judge in that episode says Kenny's play was enjoyable despite being the most offensive thing she's ever seen, praises him for not taking himself too seriously, and ultimately awards him the win.
** In ''Who Can Sell The Most Bibles'', Spenny thinks he got the movie deal of his dreams and has sold his script to Robert [=DeNiro=], and making plans to fly to LA immediately. When one of his crew members ask "What about the bibles?" Spenny shrieks "FUCK THE BIBLES!"
* CultClassic: The show was aired on multiple networks and ultimately the plug was pulled on each of them, before the show finally ended after six seasons. Yet Kenny and Spenny maintain a devoted following to this day. The creators and fans alike clamored for a long time to get the show on Creator/{{Netflix}} (who just weren't interested), until Kenny finally gave back to the fans by [[https://www.youtube.com/playlist?list=PLRSR9GR4CP7ivjS-_HzEJzG_yuS83vq3B putting the show's entire run]] on his Website/{{Youtube}} account for free.
* EnsembleDarkhorse:
** Brendan, Kenny's sound guy, is beloved for his sense of humour and gets the most screen time out of any crew member.
** Corporate Sean Francis only appears in one episode, but is regarded as one of the best judges to ever appear on the show, as his over-the-top reactions to Kenny's laziness and Spenny's incompetence led to many humorous scenes.
* SugarWiki/HeartwarmingMoments: In the episode "Who do kids like more." Kenny bribes the kids with candy and toys, while Spenny takes the kids on a city wide scavenger hunt. [[spoiler: Spenny still loses, but the single kid to vote for him over Kenny was pretty touching.]]
* JerkassWoobie: Spenny is considered this by some. His moralizing can be ham-handed and condescending, which reflects badly in some of the more socially-oriented challenges, and he only looks like more of a stick-in-the-mud compared to Kenny. Even then, Spenny gets tortured so much on the show that it's hard not to feel a little sorry for him at times, even if you're a fan that considers him the ChewToy.
* JustHereForGodzilla: "Who Can Stay Tied to a Goat the Longest" is the first episode that several newcomers to the show watch [[VideoGame/GoatSimulator due to another goat getting named Pilgor]] as an explicit ShoutOut to Kenny's.
* MoralEventHorizon: In "Who Is Funnier", Spenny is convinced that he is HIV positive because of a letter Kenny had forged, leading him to feel depressed and perform miserably during the challenge. Kenny then uses this practical joke as his own entry and wins.
* NauseaFuel:
** Their humiliations are often this. Ranging from scraping off the plaque on their tongue and forcing the loser to eat it, to having to eat a pig's head snout-first and drinking it down with milk, to being puked on by the whole crew.
** One humiliation had Spenny unclog a public toilet with his own bare hand.
** The entire meat eating episode is gross, as Kenny and Spenny both eat over a dozen pounds of meat, but it reaches a crescendo when Kenny gets sick and starts puking all of the meat back up.
** Out of all the competitions, "Who Can Keep a Dump in their Pants the Longest" is easily the most stomach-turning. Made even worse when a deleted scene reveals Kenny had tricked Spenny into having dog feces added into his diaper.
--> '''Kenny''': "The fact that you haven't changed the channel yet means that you guys are disgusting."
** The octopus challenge is considered "too gross" even in-universe, but it gets even worse when Spenny starts rolling around on his own feces while high on acid.
** In "Who Is the Better Boxer", Kenny locks Spenny in a room for a full day, forcing him to use a bucket as a toilet. Spenny retaliates by throwing the contents of the bucket directly into Kenny's face as soon as he is freed.
** A deleted scene from "Who Can Blow the Biggest Fart" has Kenny defecate on Spenny's meal. The result is shown up-close, being punctuated by the entire crew gagging afterwards. To make matters worse, Kenny then carries the plate around and tries to get Spenny to eat pieces of food that didn't directly touch his feces.
* OneSceneWonder: Mario Maiato, the fishmonger from the Octopus episode, has less than two minutes of screen time, but attracted a lot of attention due to his eccentric behaviour, namely putting an octopus on Spenny's head while humming the Bridal Chorus.
* RootingForTheEmpire: Kenny is a VillainProtagonist whose pranks often cross the MoralEventHorizon, but his cleverness and the fact that his main target can be a major condescending jerk make it near impossible not to root for him to win.
* {{Squick}}:
** In the "Naked" episode, Kenny says that Spenny's "old man ass" deeply disturbs him. Cue a close-up shot of Spenny's cellulite.
** In "Who Can Have More Fun" and "Who Can Produce More Semen", Kenny pleasures himself with a pack of ground beef.
* TearJerker: In ''Who Can Sell The Most Bibles'', [[spoiler:Spenny plans on leaving for Los Angeles after believing he has been given over 400,000 dollars and a movie deal with Robert [=DeNiro=]. Kenny, knowing that none of this is true, begs Spenny to stay with him, and his family, and their friends, and the show. When that fails he quietly asks if he could come along and maybe Spenny could help him good connections in the movie business. When Spenny says no to this, Kenny meekly says he'll buy a plane ticket anyways so that they wouldn't have to say goodbye forever. Spenny tells him not to, and that he is done with him and the show, and all he wants is the money and fame.]]
* ValuesDissonance:
** Kenny's always been the anti-PC type, and his jokes have always been tasteless, but the way he sometimes treats women on the show wouldn't fly so well nowadays. His RunningGag of goading women into kissing him on the cheek, only to turn around and kiss them on the lips, is more frowned upon nowadays than it was in the mid-2000s, and (especially on the back of the [=#MeToo=] discourse) his advances on Spenny's cousin Bianca are uncomfortable, to say the least.
** The big twist of "Who Can Bone More Women" is that [[spoiler:the person whom Spenny was getting sexual favours from turns out to be a transexual woman. Kenny then asserts that none of Spenny's points count, since his date was "really a guy"]]. For obvious reasons, this comment can be interpreted as transphobic in the New '20s. Kenny has admitted that, were they to do the competition today, he wouldn't use that tactic because by modern standards it would have gotten Spenny the win.
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