Wrestling has a lot of attempts at "humor" that usually fall flat (Hornswaggle, Eric Young). More often, the funniest moments in wrestling are unintentional (Shockmaster). But what is the funniest bit of intentional humor ever produced?
Steve Austin randomly popping up on ECW as STEVE-A-MANIA. The first time I saw it was when we were watching my roommate's latest batch of ECW tapes and had no idea it was coming, and it just FLOORED me. We rewound it a bunch of times because it was just so awesome. Monday Nyquil was also great, but the surprise and random nature of the first Austin appearance was so much more effective. I'd also vote for Mikey Whipwreck getting trained for the ladder match by Public Enemy, as TPE were marginal workers at best, but Rocco had some awesome comedic timing. The Kevin Nash run in TNA with Austin Starr (Aries), especially the wacky battle royale with Nash on commentary where Starr debuts, is tremendously funny stuff too. It was apparent that Nash was being given free reign to do whatever he wanted while drinking as much as he wanted and it produced some insanely quotable stuff. That Nash I can live with.