The entire "Rudy the Undead Hound" discussion from the second podcast.
Any time the players engage in the Vitriolic Best Buds act, but perhaps the best example comes up early in season 4, when recapping the previous season's finale.
Mike: I feel like it was a clean job. Scott: Yea, we only lost the redshirt.
The second PAX game was outrageous.
Wil: You guys, I saw a lot of necromancers when I was in Hell.
Scott: When you were in 'Nam?
Jerry: Not Nam, Hell!
Wil: Nam was hell. "Necromancers are dicks, you guys. Necromancers are dicks." Aeofel just stares off, the wings beating beneath him, his silvery hair blowing out behind him, a thousand-square stare in his eyes. He feels nostalgia as a standard action. A single tear falls from his perfectly black, orbular eye, and turns into a diamond as the wind catches it and carries it away.
In the 2014 PAX game, Morgan Webb asking during a male NPC's description of a female NPC "Is she prettier than me?" in a slightly neurotic way. She had Mike, Jerry, and Scott all keeled over laughing. Probably something you never thought you'd hear during a D&D game.