The entire Bombchu Bowling minigame from episode 4, where Tyler runs out of Rupees, has to go and grind for them, and by the time he's come back, Josh is still stuck where he was before. It comes down to the wire and Tyler wins!
The intro to the second part of Episode 4. Words cannot do it justice.
Tyler Cinching the victory from Josh at the last second, entirely because of Josh's stupidity note He spent the majority of his massive lead hanging around the runner trying to get him to stop, not knowing he doesn't stop running until night, while the winner knew right away to play the sun's song to get him to rest.
What makes this even better is Josh's earlier claim that the only way Tyler would beat him was if he did something stupid.
Tyler says he wishes he was a skeleton, Josh replies he is a skeleton, just covered up with other stuff. Then later Tyler says he wishes he was a flaming skull, and Josh tries to make the same joke again, even though it no longer works.
The entire recap portion of episode 6, which has Josh talking like a rapper while muffled rap music plays in the background.
Josh: I think you've gotten too far ahead of yourself...
Tyler: Siri, this is the last time I ever listen to you!
How the episode ends: Josh gets the Biggoron's Sword, but hadn't made ANY mention that he was close to getting it for the past several minutes. So once he gets it, he just suddenly starts giving an out-tro, much to Tyler's confusion.
Episode 7 ends similarly, save that it's Tyler giving Josh a taste of his own medicine. Josh being utterly baffled at the very end of the video really makes it a hilarious moment.
Episode 8 has Tyler repeatedly trying and failing miserably to make a Soviet Russia joke.
Tyler: In Soviet Russia...blue fire don't melt ice.
Josh: Quit while you're behind.
The intro to episode 9 consists of Josh narrating the game in a Valley Girl voice. This is made even better by just how reluctant Josh is to do it.
Tyler somehow even convinced him to use the word "ratchet" as slang, despite Josh vehemently expressing his hatred of the word during a Mario 64 video.
During the Water Temple, Tyler makes a mistake and forgets to get a key, which puts him far behind Josh. He spends the rest of the temple bemoaning how that screw-up could cost him the win...which it did.
The end of the Water Temple. Even though Josh wins, Tyler still manages to nearly make him have a heart attack (paraphrased a bit):
Josh: (kills Morpha) Thank you all for watching!
Tyler: (still fighting Morpha) ... Have you gone into the portal yet?
Tyler: (just finishes killing Morpha) Really?! I'm just going into the portal now!
Josh complaining that Tyler always brings up "shitty music" in every single video and they keep having the exact same conversation every time. Ironically, Josh's complaining about it itself then becomes a Running Gag.
Josh and Tyler play the "Silent Game" in Episode 11 part 1. It lasts a good ten seconds before they both burst out laughing.
The intro to Episode 12.
In episode 13 Josh's stupidity strikes again: He makes the wrong choice in a dialogue tree at the beginning, prolonging the conversation, and then he forgets the map and a gold skulltula. The kicker comes when Tyler subtitles Josh's screen with the items crying for him to come back.
Even worse in episode 14 when he completely forgot the Boss Key right as he approached the Boss Door.
Tyler "roleplaying" in the bloopers of Episode 15.
In episode 16, Josh tries to announce his win in the usual way, only for Tyler to completely ignore him and keep on a tangent he was singing about previously, causing the winner to get angry at the loser for not acknowledging him.
The episode summary for the final episode, especially this:
Josh Narration: And then that girl Zelda gave Link the Light Arrows, yeah dawg, roof roof!
Tyler has a couple of Malapropisms involving people's names in the finale, including giving Extreme Home Makeover`s presenter Ty Pennington's name as "Tom Hanks" and, when asked to name a professional tennis player, saying "Michele Bachmann".
Not to mention Tyler finally admitting that he listens to shitty music.
Josh: YOU ADMIT IT!
There was also Josh's reaction to losing his first full versus to Tyler.
Josh: You know what my favorite part of the versus was?
Josh:NOT FUCKING LOSING!!!
And, even though it came nearly a year late, the Loser Challenge delivers in many different ways. Poor Josh has to consume a smoothie/milkshake/hell-blend of Lon-Lon almondmilk, spinach (leaves from the Forest Temple), hot sauce (lava from the resting place of Volvagia), water (from the body of Morpha), coffee beans (lost souls captured in the Shadow Temple) and chucky salsa (from the Spirit Temple?).
The whole thing is a disaster from start to finish. Our unlucky contestant can barely manage to get the concoction into his mouth before gagging and retching violently for several minutes. For bonus points, the moment when Josh attempts to drink the smoothie is accompanied by the "Opening Treasure Chest" jingle from Legend of Zelda, which peters out as he chokes and spits it out.
Made even worse by the fact that Josh had already done the Loser Challenge before that point. The original recording was lost and he had to do it again so people would stop thinking he hadn't followed through on it.