Warning: Unmarked spoilers ahead.
Kenny
Watching Kenny on this show is a masterclass in tactics, or at least Vulgar Humor.
- 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.
- "Who Can Sell The Most Bibles" is one of Kenny's defining moments. He derails the competition by having fake Hollywood agents tell Spenny that a script he wrote of a children's movie was going to be turned into a movie featuring Robert DeNiro (Kenny even hires a DeNiro impersonator). Spenny gets visions of grandeur, buys Bibles off of Kenny just to prove he doesn't even care about the show anymore (giving Kenny the win in the process), and flies to Los Angeles to meet producers that don't exist. It's not often that the crushing of someone's dreams is this entertaining, and one would almost feel sorry for Spenny getting owned this hard if Spenny wasn't so hungry for money and fame.
- "Who Can Stay Naked The Longest." Kenny needles Spenny the whole episode by saying that Spenny wearing a watch means he's not naked (even wearing a gigantic watch around his own waist to prove his point). Spenny finally relents and leaves it on his desk. The next day, the competition ends after 72 hours, and the second it does, Spenny puts his clothes back on... which is when a still-naked Kenny reveals he put Spenny's watch ahead five minutes along with all the other clocks in the house. Oops.
- A rare moment of Awesome during a humiliation: Spenny puts terrible pictures of Kenny on a billboard with the caption "Kenny Hotz is a LOSER" and gets him to stand in the street to be called a loser by the public. Kenny starts dancing in the street, because he's so much of an extrovert, he just loves the attention! (Or as he puts it, "my fucking picture's like 50 feet high!") It's only after a few minutes that Spenny realizes he just wasted $3000 to stroke Kenny's ego.
- Kenny's entire Wounded Gazelle Gambit from "Who Is The Best Figure Skater," which goes off without a hitch from The Reveal until it finally dawns on Spenny he's been played for a sucker.
- The fart Kenny lets out on the stairs in "Who Can Blow The Biggest Fart" is a moment of Awesome in and of itself. That thing was a full ten seconds!
- "Who Can Win A Cockfight." Once they're in the "cocktagon," Kenny scores a Flawless Victory on Spenny by strapping mace, Roman candles and a flamethrower to his dick, and hitting Spenny with everything at once. Kenny had a huge grin on his face the whole time.
- "Who Can Survive On An Island The Longest" is one of Kenny's finest long-cons, where he relaxes at a Cuban resort, which is on an island, leaving a stubborn Spenny to do the competition himself. Eventually, Spenny realizes he's proving nothing to anybody, meets Kenny on the beach and tells him he'll finally relax and have some fun with him. Kenny and Spenny run into the water, but Kenny intentionally lets him hit the water first... which means Kenny wins.
Spenny
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, who can barely walk ten miles much less run them.
- "Who's The Better Rapper" has Spenny show up at the last minute to beat Kenny at the rap competition, with a posse and dancing girls. This after Spenny, in a rare moment of Spotting the Thread, finds out Kenny was faking a threat of gang violence just to scare Spenny away from competing. Spenny earned this particular W.
- "Who Can Stay Awake The Longest." Spenny didn't get the win, but he gets a moment of Awesome just for staying awake for over three days with no caffeine or stimulants of any kind, which is pretty impressive.
Other
- 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.
- "Who's The Best Pro Wrestler" and every single appearance of THE IRON SHEIK.
- Jeff, from "Who Do Disabled People Like More," reveals at the last minute that he's a fan of the show, and knew the entire time that Kenny was impersonating Spenny and intentionally being obnoxious, and then he votes for him anyway just because he loved his strategy.
