Having a quick reflect on his in ring career, it's kinda crazy that Triple H had been an active wrestler since when I started watching, to the present day retirement, long part time stints in recent years notwithstanding.
As such...
Fave Five Triple Haitch matches (in chronological order)
Vs Cactus Jack: Street Fight (Royal Rumble 2000)
Foley put HHH on the map with this one, the build has Triple H at his scummiest, forcing Foley to dig deep and bring out the persona to get the job done (wonderfully sold by Triple H who shits himself at a man changing his clothes).
The match makes its weapons work, there's a thin line between restraint on overdoing the hardcore weaponry and delivering the violence expected from the stipulation, and I think the match toes it perfectly. The Pedigree onto the tacks is a primo finish as far as I'm concerned, it's just not the sort of move you expect someone to take into the tacks, but Foley isn't any normal guy lol
Vs The Rock: Ironman match (Judgement Day 2000) (or alternatively their Backlash 2000 encounter, not so much as a match, but as a clusterfuck spectacle with the most hype finish)
It's a shame that the 2000 HHH/Rock feud never really had a clean finish, seriously, going from Wrestlemania 2000 all the way to Summerslam 2000 (with a gap for Fully Loaded) it's shenanigans central when it comes to the endings of each match involving both men.
Of these though, Judgement Day stands out as the best actual match if you have patience for 60 minutes of this. As I recall Triple H had been pushing hard to do an iron man match for a year, he finally got his wish, and to contrast it to the HBK/Hart original, it went all in on multiple falls, tactical DQs and more.
As hype as Taker's return is, the finish is something of a SWERVE as a result leading to some needless hot potato with the belt. Regardless, a fun combo of actual graps and attitude era tropes.
Vs Shawn Michaels and Chris Benoit (Wrestlemania 20)
Obviously this comes with the huge caveat of having Benoit in here, his insertion into the HHH/HBK forever war was a massive breath of fresh air for a feud that started out incredibly hot with Summerslam 2002 and the Elimination chamber's debut later that same year, only to fall into diminishing returns with the three stages of hell, last man standing and later after this mania match, the never ending hell in a cell.
At this point Trips was still very much reign of terror, and this right here was the beginning of its end, barring the Orton mess later in the year, Triple H was finally relinquishing his death grip on Raw's main event scene (not without two more mania main events mind you) and had Benoit go over leading to an ending scene post match that would be an all time tear jerker if.... well, y'know, fucking Benoit.
Generally Triple threat matches had something of a stigma, in some ways they still do, especially with WWE overusing them at mania after this match, maybe we can blame this match being too good as part of the problem, everyone plays their role perfectly and the action is tops from bell to bell.
Vs Undertaker: Hell in a Cell (Wrestlemania 28)
I was picking between this or the three stages of hell against Austin, while I usually tut and wag my finger at triple H's spectacle matches that go on far too long, this one is so stupid, so overbooked, full of such nonsense and HIGH DRAMA that it wraps all the way around into being hilarious. Sorry Austin, it's been too long since I actually watched that match, this however still sticks in my mind.
The most sports entertainment match you'll ever see that isn't cinematic, witness HBK overselling kick outs...as a referee, behold Taker and Triple H using their clout to use unprotected chair shots while imagining Vince fuming in gorilla, marvel at the constant dialogue in the ring "END IT OR I WILL".
The sweet chin music into pedigree near fall is an absolute all timer, so many including myself bit down on the bait that Triple H's ego was about to have him break the streak.
Also the cell gets its own metallica entrance music, god this is so wonderfully dumb.
Vs Daniel Bryan (Wrestlemania 30)
Though it was rather rare in a post quad injury world, Triple H could still go out and have a more traditional match that makes you wonder why it didn't tend to happen more often. There was always the underlying fear that despite wanting to believe that Bryan's victory and path to the title match main event was a foregone conclusion, that WWE were gonna WWE and Triple H would win for the evolution power hour.
Fortunately logic prevailed, from the contrasting entrances (God Emperor HHH vs Bryan just coming out as a normal arse wrestle man) to a clean as a whistle finish, this one was booked pretty much perfectly.
Bottom Five Nipple H matches
Vs Scott Steiner (Royal Rumble 2003)
A case of both men being a vortex of suck at the time, I don't know if they were both injured/out of shape/gassed or if it's just bad chemistry but these two shit up the joint and Steiner went from immediate main event push to midcard purgatory as a result.
As a bonus, they also shat up the joint again with a sequel a month later.
Vs Booker T (Wrestlemania 19)
It's been touched upon in this thread, an angle whose promos would absolutely not fly today and it's actually shocking they scraped by in 2003, perhaps it did in part because everyone rightfully assumed that this was all some real real cheap heat to maybe if nothing else, make Booker's victory all the sweeter.
The match itself is actually fine, up until the ending, oh god that ending, not only the decision for Triple H to go over in a feud where his role was barely disguised mega racist, but to do so with the longest gap between hitting the finisher and pinning that I've ever known, absolutely tone deaf.
And this comes right after the Steiner matches
Vs Orton (Wrestlemania 25)
Take a blood feud with months of escalating momentum behind it, kneecap it immediately with a dumb DQ=lose the title stip, and that's just one reason this match is the drizzles.
The one sided finish in favour of Triple H is supposed to be some kind of cathartic triumph over Orton's months of dickery, yet it falls completely flat after a tedious match, after Taker/HBK rocked everyone's socks and potentially because it would be more interesting for Orton to have actually won this one.
The one time faction run ins should've been encouraged
Vs Kevin Nash: Sledgehammer Ladder Match (TLC whatever year, 2011?)
On one hand you could say this was better than it had any right to be and at least has comic value.
On the other, it stands as the end point of WWE's complete bungling of CM Punk's pipebomb, somehow it led to Kliq buddies having a ladder match over a saga of "who sent the text?!" and making Johnny Ace an on screen authority figure.
Truly a marvel of bad booking exploits to reach this unwanted conclusion, two oldies with no business in a ladder match fighting a battle no one was interested in watching.
DX vs Brothers of Destruction (some saudi arabia blood money event)
Imagine HBK coming out of retirement for one more match, and it was this hot garbage, okay granted I've never sat and watched the thing but I choose to accept the consensus and the gifs.
Every participant looked like a pile of poop out there, botches galore, accidental unmaskings, a past their prime mess.
If Kane hadn't basically buried himself to me over the last two years especially, I'd have reserved a spot here for the Katie Vick feud ending match where Trips did Kane dirty, but his moronic tweeting arse no longer gets that luxury, instead Kane can take the dishonour of being the shittiest performer in a shitty match here.
