Awesome Funny Heartwarming Main Trivia Wrestling YMMV
Comprises most of the examples on the DX page, but the skits when they parodied The Nation (at the time, led by The Rock) are pretty much carried by him. Hunter as "The Crock", X-Pac as "Mizark", Jesse James as "B-Lo", and Billy Gunn as "The Gunnfather", with fan Jason Sensation as "The Nugget" Owen Hart.
Done in a flashback sequence, where he confirms to Stephanie that her father, due to an attack on Nexus, is still brain dead...as pillow talk.
Triple H is eventually put on a Survivor Series team with Kane, Jeff Hardy and Rey Mysterio Jr. When they confront him for the crap he's pulled, he gives a sheepish "my bad" reaction to both Kane (for the Katie Vick incident, wincing and facepalming while it's described) and Jeff Hardy (who brought up that Hunter put him in the hospital once).
Actually saying Zack Ryder's Catch Phrase on Raw. Especially because you can see how painful it apparently was for him to put Ryder over.
Just before that, responding to Christian complaining about Sheamus throwing him back into the ring & costing him the World Heavyweight Championship with "It was a Lumberjack match, dumbass!"
He's the only reason the "McMahon Family Reunion" segment from the 15th Anniversary Raw is even watchable. It's just one CMOF after another for him:
While most agree that the "Katie Vick" angle is about as tasteless as it gets, Triple H's account of what went on behind the scenes is, arguably, another story.
Convinced that Hornswaggle (back then named Little Bastard) was Mr. McMahon's son, Triple H asks him questions about him. This one is a shining example of funny:
"About his mom...was she magically delicious?"
Book Ends / Call Back: Back in 2000, a backstage segment featuring Triple H and Trish Stratus involved the former attempting to stretch out the latter from behind. Cue Stephanie McMahon (then his manager and on-screen wife at the time) walking in on the both of them as it happens.
After the Raw taping for October 28, 2013 ended, Triple H informed the booing fans that he was ejecting them from the building (after having just done the same to Big Show). They refused, so he decided to hire the whole audience into WWE. Immediately after,
"You're fired! Get the hell out of my building!" Although it was followed by a brutal and hard-to-watch No-Holds-Barred Beatdown, his fourth-wall-busting quip about the policemen arresting Daniel Bryan(who have been somewhat a Running Gag in very personal WWE feuds over the decades) not being real cops was Actually Pretty Funny.