For the Wrestling/DGenerationX examples, head [[Funny/DGenerationX this way]].
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* A subtle moment. After he & Eddie Guerrero are KO'd by Kurt Angle, Chyna checks on them and Triple H is shown, from the looks of it, [[https://i.redd.it/w5z6jwha6ld41.gif trying to unzip her shorts]].
* His response to the hypothetical question of "what if the Montreal Screwjob had happened to Shawn instead of Bret?"
-->'''Triple H:''' ''Nothing. [[HeterosexualLifePartners We're]] not that stupid.''
* Before the renewal of the wedding vows ceremony between Trips and Stephanie, Trips found out that Stephanie had been lying to him about being pregnant and had even hired an actor disguised as a doctor to sell the story. Fast forward to the ceremony itself, and after Stephanie has given her (extremely sappy) vows, the minister invites Triple H to give his. Hunter turns to the camera with a sly little smile that just screams "Watch this."
** Made even funnier by the crowd going crazy and by JR and the King on commentary.
--->'''Jerry "The King" Lawler''': [[ThisIsGonnaSuck Uh-oh.]]
--->'''Jim Ross''': Yep.
* A few weeks later, after that wedding, Stephanie's fake pregnancy was brought up, and she went on to say that in the bedroom, Triple H had always come up [[TeenyWeenie a little bit short]]. Hunter would retaliate by delivering this hilarious insult:
-->'''Triple H:''' You see Steph, even a 747 looks small when you're flying into the Grand Canyon.
* Done in a flashback sequence, where he confirms to [[Wrestling/StephanieMcMahon Stephanie]] that her father, due to an attack on Nexus, is still brain dead...as pillow talk.
** Even funnier when you realize [[TheUnseen he's never actually shown onscreen]]. You know it's him because of his voice.
** Given the way WWE [[RetCon mangles]] [[ThreeMonthRule canon]] to suit its own interests, it would have been all too easy to [[WhatCouldHaveBeen make an entire angle out of the voice not belonging to Trips.]]
* Trips is eventually put on a Survivor Series team with Wrestling/{{Kane}}, Wrestling/JeffHardy, and Wrestling/ReyMysterioJr. [[https://www.youtube.com/watch?v=oZ4D1KhzbfU 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).
* [[https://www.youtube.com/watch?v=7ghVLn4TUeg This appearance on MAD TV,]] where Trips is PlayingAgainstType. Kind of.
* Actually saying Wrestling/ZackRyder's CatchPhrase 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:
--> ''"For some reason, Vince, I feel like I'm part of your family. [[LeaningOnTheFourthWall What's up, Steph?]]"''
--> ''"Abe Knuckleball Schwartz? What, was [[Wrestling/SteveLombardi the Brooklyn Brawler]] sick?"''
--> ''"Pat Patterson - well, no one's shocked to see you out here."''
--> ''"Heh, Steph, see you at home... [[LameRhymeDodge I mean, your brother's a gnome]]!"''
* While most agree that the "Katie Vick" angle is about as tasteless as it gets, Wrestling/TripleH's account of what went on [[https://www.youtube.com/watch?v=y2v7pFpe76c behind the scenes]] is, arguably, another story.
* Convinced that Hornswoggle 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?"''
** When Hornswoggle was revealed to indeed be [=McMahon=]'s son, Triple H proceeded to laugh so hard it looked like he was going to pop a blood vessel.
* Back in 2000, a backstage segment featuring Triple H and Wrestling/TrishStratus involved the former attempting to [[DoesThisRemindYouOfAnything stretch out the latter from behind.]] Cue Wrestling/StephanieMcMahon (then his manager and on-screen wife at the time) walking in on the both of them as it happens.
** Then Steph asks him to teach her the move he was showing Trish, which goes fine until he calls Steph [[ThatCameOutWrong Trish.]]
** Flash Forward to RAW 1000, where Trish is now a guest on the show and attempting to teach Triple H yoga. Inversely, it's Trish from behind this time. [[RunningGag Cue the rest of D-Generation X walking in on them]].
** And the ending of an intergender match between HHH and Trish against The Rock and Lita... [[https://i.ytimg.com/vi/0E97lOxYLlg/maxresdefault.jpg well, see for yourself.]]
* [[https://www.youtube.com/watch?v=WVAsNsjVUXs 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, [[spoiler: [[GeorgeJetsonJobSecurity "You're fired! Get the hell out of my building!"]]]]
* Although [[MoodWhiplash it was followed by a brutal and hard-to-watch]] NoHoldsBarredBeatdown, his [[NoFourthWall fourth-wall-busting]] quip about the policemen arresting Daniel Bryan (who have been somewhat a RunningGag in very personal WWE feuds over the decades) not being real cops was still funny.
* Trips parodying Teddy Long's RunningGag of making Tag Team Matches during his tenure as Smackdown General Manager on the 9/5/2014 edition of Smackdown. Even complete with Long's old theme music and his 'Holla!" CatchPhrase. [[http://youtu.be/bo-Y50NUvSw Watch it here.]]
* While it never made it to air, we have [[https://youtu.be/z8KbXThVBFI this gem from "Best of Raw After the Show"]], where Triple H's attempted rope maneuver is countered by a kick to the chin... prompting him to [[YouCanBarelyStand wobble in place]] for a full ''[[OverlyLongGag minute]]''. Meanwhile, Shawn Michaels can be seen trying to literally blow him over from one corner using a few different methods, while Ric Flair shouts "No! No champ, no!" in the most pathetic voice ever. After recovering, Trips promptly pulls a FacePlant while facing Ric Flair, the premiere user of that particular sell in modern wrestling.
* During the contract signing between Wrestling/JohnCena and Wrestling/DanielBryan for the infamous Summerslam '13 match, tensions escalate as usual and Cena flips over a table and tries to antagonize Bryan into hitting him. Cue Triple H coming out to restore order. Before he gets between them, Triple H jokingly tosses the table around again, taking all the piss out of the situation.
* After Hunter gets a concussion against Curtis Axel, Vince refuses to let him compete at all. So Triple H books himself in a rematch against Axel, and sure enough, Vince comes to stop it, ordering the bell to be rung and making Justin Roberts announce that Curtis Axel has won [[YankTheDogsChain as a result of a DQ.]] An angry Trips [[ScrewTheRulesIMakeThem then orders the match restarted]] on his authority as COO, and just as they get going again, Vince returns, rings the bell again, [[KickTheDog and rules that Triple H has lost by forfeit.]] Now Triple H is really pissed, so he gets in Justin Roberts's face and orders him to announce that the match will restart once again... as a 60 minute Iron Man match! Vince, after a hilarious stunned expression, counters by ordering Axel out of the ring, [[EvilIsPetty then stealing the ring bell and the ring announcer's microphone!]]
* It's pretty amusing to see that WWE's PG rating is still somewhat of a foreign concept to Triple H. During the 2016 Royal Rumble [[spoiler: after eliminating Roman Reigns,]] HHH very clearly is shouting "FUCK YOU, MOTHERFUCKER!!!" while crotch-chopping like crazy.
* Triple H temporarily replaces Roman Reigns's spot in Wrestling/TheShield during a house show in the UK because Reigns had a bad case of meningitis. Some of the best moments from HHH's brief Shield tenure include:
** Rollins's way of introducing Hunter to the audience: Using a CallBack of Hunter's "Plan B" promo that causes The Shield to break up for the first time.
** [[https://www.youtube.com/watch?v=50abE6gKDjI Triple H nope-ing out of a suicide dive.]]
** [[https://youtu.be/vbJ9NyCbeeQ?t=1m32s When The Shield tried to put Cesaro into the triple powerbomb position]], Hunter instead tried to put Cesaro's head in the position for a ''Pedigree''. Clearly 20+ years of using the Pedigree as a finisher causes HHH to forgot that he's supposed to do a triple powerbomb instead.
* And here's Trips after Survivor Series 2017, where he got powerslammed by Braun Strowman, [[https://twitter.com/nicolesbrianna/status/932457068992319494 looking like last call at the bar.]]
* Hunter [[https://www.youtube.com/watch?v=QsSxRElRe1I steals Lip Sync Battle]] right out from under [[Wrestling/StephanieMcMahon his wife]], Wrestling/TheNewDay, and Jimmy Fallon. By singing "How Far I'll Go" from ''WesternAnimation/{{Moana}}''.
* [[https://twitter.com/bossmoz/status/957833464140541952 Here's Hunter backstage]] secretly taking photos of [[spoiler:Ronda Rousey]] following her WWE debut at the 2018 Royal Rumble.
* On an episode of ''[=SmackDown=]'' in 2002, in his match with Kurt Angle, Triple H pulls down Kurt's tights to expose his ''thong''. And then, at the announcer's table, HHH looked at the crowd for a bit before slapping Angle's bare butt cheeks.
* At Wrestlemania 25, Undertaker and Shawn Michaels had one of the best matches in Mania history, both go backstage and collapse, no doubt tired from the work they put in. For context, Taker vs. Shawn was not the main event, it was third to last, meaning both world title matches had an uphill battle to surpass it. Triple H walks in, tosses the WWE title aside and yells "How the fuck am I supposed to follow that?".
* At King of the Ring '98 Hunter joined the commentary while Chyna joined the Spanish commentary. Lawler notes that Chyna is bilingual and asks if Hunter is, too.
-->'''Triple H''': [[HoYay I'm bi- a lot of things, but lingual is not one of them]]. [[ThatCameOutWrong Wait, did I mean to say that]]?
-->'''Jim Ross''': Probably not, but we're live.
* What was Triple H's caption on the photo shaking Wrestling/CMPunk's hand and welcoming him back to WWE?
-->'''Triple H''': Mighty cold day in hell.
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