One of the funniest episodes of When Cheese Fails left Jeff and Adam completely and totally confused when a probe starts building pylons and cannons in an empty corner of the map. They tossed up some theories on why he was building stationary combat structures in the middle of nowhere until they go to the player's view to see that he was attempting a cannon rush on a base that wasn't there. As soon as the probe moved into visual range of what should have been the enemy base, the player immediately quit, and thus the introduction of the FAIL stamp. Almost the entire second half of the video is Jeff and Adam laughing uncontrollably while trying to figure out what happened.
In a similar vein, there was one video from a cold cast marathon where a Terran player tried to cheese by landing a Command Center in his opponent's base and converting it into a Planetary Fortress...but forgot to get any gas.
Jeff and Adam's mounting stupefaction at AlbinoFly's 14-Nexus opening build. Yes, that means he opened the game by building 14 bases and a metric ton of probes and nothing else. And it works. Adam eventually just declares both the build and AlbinoFly's victory the dumbest thing he's ever seen.
Also, the entire match ends up hinging on yet another example of what happened in the above episodes: namely, opponent Ogusku finding a wall of pylons and a probe going for a natural expansion, and concluding he'd found AlbinoFly's main base instead of his sixth, resulting in a lot of wasted time. Possibly invoked by AlbinoFly; he doesn't do that wall of pylons at any other bases.
Adam: You know, I haven't seen The Breakfast Club in a long time, I should probably watch it. Jeff: The hell are you talking about, Adam?! What are you talking about, seriously? You haven't seen The Breakfast Club? You know what you haven't seen, a diamond. And I did! In fact, I've seen two of them. Adam:Prove it. (Beat) Jeff: ...Dick move, bro.
Gets an amusing Call-Back at the end of the game when the pair, frustrated with the entire Temple of the Gods series, gets some catharsis by planting TNT around the village and blowing it up. At one point Jeff chases a pig into a hole in an attempt to wall it in with TNT...and Adam walls Jeff in, then lights the fuse. Cue little girl scream from Jeff.