I'm pretty sure the thing that had me laughing the most out of what I've listened to (about 40% of the site content) was Aaron and Tom's interaction in Bryson Springs (starting at about 1:13:30) that culminated in a fistfight and Aaron's professor character knocked out, shoeless, and handcuffed in the back of a police car with a mafia hitman. Caleb's reaction to them had me dying. A highlight reel of all the damage Aaron took in that session (which stands out as my favorite AP yet) would be pretty great, too.
From the Wild Talents campaign, the escalating comedy of errors that led to Aaron's Hobot becoming the feared ROBOT ASSASSIN of New Arcadian headlines would be funny (I think) to hear all at once.
Not picking on Aaron, but between dubious choices and poor luck he has created some of the funniest moments I've encountered in roleplaying outside my own table or KoTD.