The legendary entrance of The Shockmaster in WCW. You gotta give the other wrestlers and the commentators credit for not busting out laughing after seeing it. This didn't stop the commentary from losing it, though, and even the British Bulldog can be clearly heard saying "He fell right on his fucking arse!"
You can hear Ric Flair losing it as well, exclaiming "Oh god! Oh my!"
Back in ECW, Joey Styles had some pretty funny one-liner reactions to what was going on in the ring. One of the things he would occasionally say (aside from replacing his trademark "OH MY GOD!!!" with "AY DIOS MIO!!!") happened whenever a luchador jumped from the ring so far he landed in one of the first few rows: "And it's Take-Home-A-Luchador night here in the ECW Arena!"
(as the crowd breaks out into a chant of "Holy shit!") "My mother's gonna hate me for sayin' this, but...HOLY SHIT!"
The poor production values alone added fuel to the fire. Since typical ECW shows didn't have the big screen displays common in WCW and WWF/E, and since a match that starts in the ring isn't guaranteed to stay in the ring, parts of the crowd can end up left in the dark. One match involved two wrestlers brawling out behind the bleachers in one half of the building while fans in the other half chanted, "I CAN'T SEE SHIT! I CAN'T SEE SHIT!"
It is hard to choose the funniest moment of the Andy Kaufman-Jerry Lawler feud, but Andy's video tutorial series for the people of Memphis (Lawler's turf) on how to use soap, toilet paper, etc. is definitely up there.
On an episode of WCW Thunder, Kevin Nash served as a guest commentator. Botchamania put video of this into its 94th edition...and Nash is much more entertaining as a commentary guy than as a wrestler.
(deep voice) "Bill Goldberg, a bald-headed man with a tattoo. Who has only lost one time, to a fiercer warrior, Mister Kevin Nash!" (normal voice) "That's pretty good, ain't it—how I worked that in there?"
Hell, practically anything that makes it on Botchamania qualifies.
Also a Moment Of Awesome, there was a match in which Kevin Steen puts his opponent in a lock, only for a guy in the audience to chant "Boring! Boring!" The two combatants look up and yell "Who said that!?" They march into the crowd, find the idiot, then point at him and chant "Faggot! Faggot!" as the audience joins them.
'Inverted, as this came from the audience and it was the wrestlers'' who found it funny. The commissioner of the late Stampede Wrestling asked the audience to tone down on the swearing. At the next show, audiences chanted (at moves they thought impressive) "HOLY BEEP! HOLY BEEP! HOLY BEEP!" The wrestlers found it HILARIOUS.
From Bash At The Beach 1998: Chavo Guerrero has a hair vs. hair match with his uncle Eddie, and decides before the match he'll wrestle Stevie Ray as a tune-up. Keep in mind Stevie is about twice as big as Chavo. Eddie Guerrero comes down after both Stevie Ray and Chavo have come out, which prompts Chavo to grab a mic and dedicate the match to Eddie. After some goofing off by Chavo, he offers a handshake to Stevie. Stevie accepts......only for Chavo to YELL out in pain, collapse to his knees, and immediately tap out. Bell rings, Stevie wins via submission, and after a couple moments, Chavo grabs the mic and says, "EDDIE! That was for you Eddie! I'm so tired.......I'm exhausted! I guess we're wrestling now, right?" Chavo's performance was hilarious, and even though he lost against Eddie, his reveal that the "tune-up" was a Batman Gambit SOLELY to get under Eddie's skin (it worked) can also qualify this as a Crowning Moment of Awesome.
El Generico: Kenny Omega! Chuck Taylor! Colt Cabana: Good... El Generico: El Generico numero uno! Colt Cabana: Ah, geez— El Generico: Kenny Omega, no bueno! Colt Cabana: No. Ready...say what I say...(whispers to El Generico) El Generico: Kenny Omega y Chuck Taylor...(Colt whispers to him again) I want...I-I want to piss in your boots! (more whispering) ...and your ears! (more whispering) I EAT CHILDREN! Colt Cabana: No! (whispers) I eat your children! El Generico: Que no comprendo "eat children"...
This troper remembers one night on Nitro where Tony Schiavone had warned kids watching at home not to emulate any wrestling moves in their backyard, to which Bobby Heenan quips "Do it in your living room, it's more fun!"
Delirious emerging from under the ring with a Star Wars-themed pillow and Looney Tunes blanket (apparently Delirious was sleeping under the ring), with the pillow and blanket involved in several spots during the match
Claudio Castagnoli coming out in a bright white suit, taking the pillow and blanket and taking a nap in the middle of the ring
Austin Aries emerging from the back with toilet paper stuck to his shoe (and after his very hasty elimination, runs right back to the bathroom)
Every other participant turning on Brad Bradley, the largest competitor, and in the process managing a Total Party Kill.
From Volume 40, the crowd chants at Portia Perez "die, Portia, die".