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Eliminating Mike Knox in seconds at Survivor Series 2006, then rushing over to Triple H to ask "who was that?"
He then slides out of the ring where Melina was standing, in the middle of chewing out the commentators for badmouthing her boyfriend, Johnny Nitro. Shawn, playing some mindgames, sidles up behind her and puts his arm around her like Johnny would, in typical Sexy Boy style. Hilarity Ensues when Melina realizes who it is.
In an effort to put a rift between Shawn and Triple H, commissioner Sgt. Slaughter books a match between the two for the European title. After teasing a D-Generation X breakup all night, the two proceed to have the biggest mockery of a match in Raw history. See the entire thing here, complete with Jim Cornette's Hurricane of Euphemisms afterward.
What really makes this hilarious is Shawn's blubbering, melodramatic speech after the match.
During Carlito's Cabana, Carlito lures Shawn into a trap so he can get attacked by Chris Masters, and Shawn lampshades the hell out of it:
"You know, you'd think after 21 years of doing this, you'd think I'd be smart enough to not get myself into these situations!"
"Now I know what you're thinking...he's headlined Wrestlemanias, he's held every championship under the sun, and I don't know if I've mentioned this lately, but I sing my own theme music!"
Shawn's Twitter is a goldmine of funny, highlighting how deeply sarcastic, completely unaware of pop culture, and a total country-boy Shawn is.
From the Wild Card Match at Survivor Series 1995 in which Shawn was teamed with then-hated enemy Psycho Sid: Sid sets up Razor Ramon for Shawn's Superkick, Razor moves and Shawn hits Sid by mistake, leading to Sid being pinned. Shawn just shrugs, mouths "Oh Well" to the camera, and does this little "Missed it by that much" gesture with his fingers. Hilarious.
"It's better to be pissed off...than pissed on..." Shane and Vince definitely found this out the hard way.
Razor Ramon pulling Shawn's trunks down during the famous Wrestlemania X ladder match. A treat for the ladies, hilarious for everyone else.