- Anvilicious: 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.
- Big Lipped Alligator Moment: In the middle of "Who's the better jew?" Kenny dons a Hitler costume and performs a soft love-ballad music video entitled "where the butterflies flow".
- Crosses the Line Twice: Kenny's life goal is to see how far he can take this trope to the limit.
- 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!"
- Crowning Moment of Awesome: The few times Spenny wins usually involve a last-minute heroic triumph over Kenny.
- Spenny gets one in the "First One To Be Mean Loses" competition. After a series of increasingly mean-spirited pranks by Kenny (who gives Spenny an annoying parrot and lies that he slept with his ex-girlfriend), Spenny consumes a number of tranquilizers to prevent himself from getting angry, before laughing at Kenny and falling asleep. This is accompanied by heroic music.
- In "Who Can Win A Ten Mile Race?", Kenny tricks Spenny into attending a funeral for his (not)dead mother miles away, giving Kenny a head start. After Spenny realizes what happened, he rushes to the racetrack, runs the whole ten miles in formal clothing and dress shoes, and beats Kenny.
- In "Who Can Piss Off The Most People?", it was clear from the outset that Kenny was going to win... but he still gets Awesome points for the sheer audacity of hiring a plane to circle around Toronto for the day, towing a giant banner that says "Jesus SUCKS".
- Kenny being able to lift a basket full of bricks using his penis. While Spenny can only watch in horror. Of course, they're fake bricks, but the point is Spenny believed it.
- The entire "first to laugh" episode, where both guys pull out all the stops to make the other laugh, only for them both to laugh at the exact same time
- Crowning Moment of Heartwarming: Averted in the legendary "who do black people like more" episode. Kenny spends a whole afternoon having a serious and enlightening conversation with a black woman hired to clean the house that day. As he acts like a perfect gentleman to her, he realizes that Spenny having a black maid as a child wasn't a sign of racism, and he promises her that he will apologize to Spenny for claiming it ever was. And then he reveals that he edited the clips of the conversation between the cleaning lady in with clips of Spenny arguing with Kenny to make Spenny look like vicious racist and then shows it to the three black judges for the episode.
- Another one is from 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. Spenny still loses, but the single kid to vote for him over Kenny was pretty touching.
- Dude, Not Funny!: Some of Kenny's schemes are a tad more dangerous for Spenny. Such as his reckless use of radiation on him, or slipping him acid, turning him into an alcoholic, and locking him in a closet for a day. At least for the last one he was genuinely guilty and regretted it.
- He later admitted that he did not actually use the radiation machine on Spenny, but included the footage so that Spenny would think he did.
- Ensemble Darkhorse: While Kenny and (arguably) Spenny are more popular then him, Brendan, Kenny's sound guy, gets the most screen time of any crew member other then Kenny and Spenny.
- Fetish Retardant: For Spenny when directing his own porn film. The excitement was sort of killed for him by the fact that the actress' breath smelled "like cigarettes and testicles" and was amazed that someone had breath worse than Kenny.
- In the whoever-gets-a-boner-first-loses episode, Kenny uses LITERAL fetish reatardant to ensure his win: he gets a local anesthetic shot into his junk to kill any possible boner.
- Foe Yay, to some extent. Kenny himself regularly comments on how much Spenny wants to do obscene things with him. Spenny, of course, denies it. Whether he's being honest or not is up to you.
- Oh come on, we are just waiting for the sex/bdsm tape of the two of them to come out.....
- Ho Yay: Along with the above foeyay, there was the episode where they were competing over who could go the longest without getting an erection. For the final test they hired two strippers to give them lapdances. Kenny hired a male one for Spenny. One striptease and dance from a guy later, and Spenny lost the competition.
- In the episode "Who Do Gay Guys Like More?", Kenny looks at the camera and says that he and Spenny "have been lovers for years." before pulling down his pants and trying to get Spenny to have sex with him right there in the kitchen. It... was an interesting episode.
- Then there was the episode where they competed over who could sodomize themselves with a foot long hotdog the farthest.
- Jerk Sue: Kenny can be seen as one.
- Magnificent Bastard: Kenny. He's underhanded, devious, and often ruthless.... and he rarely gets caught. AND he's the more popular of the two. For example, in the episode "Who can take the most torture" Kenny went out of his way to make sure he lost, because that would mean Spenny ends up being tortured the whole time and all Kenny has to do is one little humiliation.
- Moral Event Horizon: Kenny took an X-ray machine and used it to give Spenny radiation poisoning in his sleep just to lower his sperm count for a competition.
- In later interviews Kenny revealed that while he did acquire the radiation machine, he never actually turned it on. He included the footage so that Spenny would think that he did.
- Nausea Fuel: 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.
- Squick: Countless examples, but the humiliation is usually where they pull out all the stops.
- Some examples are Spenny being puked on by the crew, Spenny rolling around in his own feces while high on acid, Kenny and Spenny in a bath together and of course Spenny's old man ass in the Naked episode.
- Tear Jerker: In Who Can Sell The Most Bibles, Spenny plans on leaving for Los Angeles after believing he has been given over 400,000 dollars and a movie deal with Robert De Niro. 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. Who knew that Kenny was the nice friend?
- They Just Didn't Care: Spenny is deeply frustrated when one of the porn stars he hires for a challenge is not even trying to display any emotion and openly states that he's just here for the money.
- Uncanny Valley: Dear god it is shocking how much KENNY of all creatures was able to be made into such a convincing woman.
- Unfortunate Implications: In the whoever-stops-singing-loses episode, Spenny decides to sing for a community center so as to motivate himself, and sings that he wants to get the community center a piano so they'd stop listening to rap music...