Sorry it took so long for me to return to this! Sorry too that it's so slapped together... just wanted to get it posted. Comments are probably out of order since I was aggregating matches and commenting on them to collect my thoughts before starting to rank them. I may come back to clean-up comments and revise rankings based on ensuing conversation... but for now, I'd like to present:
McMahonMania: Top 20 McMahon Matches!1.) WrestleMania XIX - Street Fight: Vince McMahon vs. Hulk Hogan
These thoughts were written in chronological order based on when the matches occurred... I went back and ranked them afterward. I'm not realizing with crazy clarity that street fights just might be to the McMahons what Hell in a Cell Matches are to Undertaker. Anyway... this works because Hogan was old as fuck, Vince was old as fuck, so it's two old men going toe-to-toe in a no-rules environment, with plenty of passionate hate to fuel reasonable (and certainly entertaining) action. We get that epic Roddy Piper surprise run-in, and Vince proves that he can jump from high things just as well as his son can. Depending on the night, this is possibly the best McMahon Match. It's certainly in the Top 5. The rest of Vince's 2003 is just too fucking weird or shameful to mention, much less make any sort of "best of" list. Actually... I take that back...
2.) King of the Ring '01 - Street Fight: Shane McMahon vs. Kurt Angle
See
Emperor's epic review for why this match gets the love it does. Kurt wrestling twice previously on this night, with Shane meddling as needed to ensure Angle's maximum exhaustion come this match... as well as Angle generally dominating Shane and winning this match... all make this tolerable enough from a logic standpoint. Then you consider the insane action during the match, and it's a winner. Tough to beat. Arguably one of the Top 3 McMahon Matches. This is for sure where Shane truly cemented his good standing with the fans. This is it for me for Shane for 2001. He didn't really do anything else noteworthy enough IMO other than participate in the Winner Take All Survivor Series Match, and like the 1999 Royal and Corporate Rumbles... that match is too "multi-man" for me to count for this.
3.) WrestleMania X-7 - Street Fight (w/ Mick Foley as special guest ref): Vince McMahon (w/ Stephanie McMahon) vs. Shane McMahon
Easily the better McMahon 'Mania Showdown (vs. 'Mania 2000, where the McMahon family imploded via proxies). As far as I know, this is the debut of Shane's coast-to-coast dropkick off the top. Pitting a non-wrestler against a non-wrestler (despite each McMahon having numerous matches and several title reigns a piece by this point) makes this much more tolerable from a logic standpoint. From an entertainment standpoint, it's hard to top. The Trish/Steph/Linda stuff blowing up in Vince's face puts this match over the top. I mean, jesus... that pop Linda gets when she rises from the wheelchair. Where are those kinds of pops these days!?
4.) St. Valentine's Day Massacre - Cage Match: Vince McMahon vs. Stone Cold Steve Austin
On the old board there was plenty of valid debate that this match could've been big enough to be the main event of WrestleMania XV (with Rock/Mankind for the title being the co-main event). The only thing I'm a little sour on is Big Show's debut, but I don't know if it just seems dumb/lackluster in hindsight because I know how poorly he'd be booked.
5.) SummerSlam '99 - "Love Her or Leave Her" Greenwich Street Fight: Shane McMahon vs. Test
Debatably better than his European title defense against X-Pac at 'Mania... I certainly enjoyed the storyline headed into this more. I think Test's green-ness and the fiery passion instilled by fighting for a loved one (whether significant other or sibling) made this buyable enough for me. Plus, Shane didn't win.
6.) WrestleMania XV - European Title: Shane McMahon (c) vs. X-Pac
Shane had wrestled a handful of matches already by this point, but this was arguably his biggest test to date and on the biggest stage, no less. And with a capable and equally sized in-ring general like X-Pac, it all came off as good as (if not way better than) could be expected. Benefits from the conclusion of the double-doublecross that sees HHH and Chyna reunite to fuck over DX and join the Corporation. Bonus points for this being the first major match to feature a McMahon either as a champion or winning a championship. Although I'm not sure what's a bonus when I really think about it... Also, I'm not a 100% sure, but did Shane face X-Pac in a Greenwich Street Fight on the episode of RAW just before 'Mania? That might be something interesting to check out... I've also never seen their rubber match from the UK No Mercy '99 PPV.
7.) WrestleMania 33 - Shane McMahon vs. AJ Styles
Fastforwarding from 2007 to 2017... Fuck Vince winning the ECW title, fuck the McMahons tangling with Legacy as if they were all peers, fuck anything else that might've happened in the interim (I doubt I'm missing anything worthwhile...) I really didn't want to be one of those people who poopoo'd on this before it happened, and so I tried to be as open-/blank-minded as possible headed into and throughout this. It was entertaining enough, I suppose. I have no real grasp on the storyline headed into this, but I knew AJ was capable of entertaining and it was interesting to see an old-but-jacked Shane still do the same things he was doing 15+ years ago. Haven't seen his matches since this, or all of his HIAC against 'Taker, but modern Shane aside from the AJ anomaly is something I want no part of.
8.) SummerSlam 2014: Stephanie McMahon vs. Brie Bella
Stephanie is horribly under-represented on this list. Her big return to the ring after over a decade, and she produces the second best match of the night.
9.) Royal Rumble '02 - Street Fight: Vince McMahon vs. Ric Flair
Flair could've debatably been considered a non-wrestler at this point. The right guy went over in a reasonably entertaining match, especially considering there were apparently plans for Flair to become an active wrestler later on in 2002, tangling with guys like 'Taker, Austin, Jericho, and other big names. Unfortunately, Vince gets his W back on Flair in June with a win in a No Holds Barred Match on RAW. I think this is were Vince reconsolidated his ownership of WWE before Bischoff debuts. I don't recall if this match was any good and haven't seen it since watching in real time, and in real time I remember having queasy feelings about the general product more often than not... so, in other words, I'm sticking with the PPV version of this match.
10.) WrestleMania 22 - No Holds Barred: Vince McMahon vs. Shawn Michaels
"No Holds Barred" being a synonym for "Street Fight", I think my theory holds true about the McMahon match specialty. Anyway... This was heralded as debatably the match of the night, but I dunno... the McMahons didn't wrestle a match in 2005, and this felt more like something slapped together to give Shawn something to do in part because of injuries and deaths fucking up the main event scene. This also led to HBK & God vs. Vince & Shane, which I must give a shout-out to but cannot include on this list. In fact, nothing else that the McMahons did in 2006 is listworthy in my eyes. That fucking DX feud was a mess, and I still wasn't over my anger about Shane being billed as an equal to Kane in 2003.
11.) Armageddon '99 - No Holds Barred: Vince McMahon vs. Triple H
Arguably more entertaining than their SD! title match, and possibly Vince's second best in-ring outing of 1999 (the Royal and Corporate Rumbles were too "multi-man" for me to count as a true non-wrestler performance, and I'm not acknowledging that fucking handicap ladder match against Austin from KOTR).
12.) No Mercy '03 - I Quit: Vince McMahon (w/ Sable) vs. Stephanie McMahon (w/ Linda McMahon)
For as fucked up as this match was in terms of build and in-ring action, it's noteworthy for what it highlights about the McMahons. I recall this being much more entertaining than it had any right to be. Also, is this the match where Vince inadvertently blades too deep and fucking gushes blood? I've got nowhere else to mention it, but the fact that unmasked murdering madman Kane had a relatively equal rival in Shane on the opposite brand was far, far more infuriating to me than the Vince/Steph mess on the Blue Brand.
13.) SummerSlam '00 - Hardcore Title: Shane McMahon (c) vs. Steve Blackman
Shane goes into yet another major PPV as a champion... at least this match gets bad ass Steve Blackman on PPV, and he goes over, and Shane takes that insane backward fall off the top of the set. That's all cumulatively worth something, I suppose.
14.) Backlash '01 - Last Man Standing: Shane McMahon vs. Big Show
Arguably better than their No DQ clash at Judgment Day 2000, but it's still dumb as hell that Shane is beating someone like Show. At least there was some Test-erference, and Shane did dive off of something tall... but then again, this wasn't Shane's first huge dive/fall, and this loss arguably cemented Big Show's fate for the rest of 2001 and most of 2002.
15.) SmackDown! 9/19 - WWF Title: Vince McMahon vs. Triple H (c)
Noteworthy because a non-wrestler (even if it is Vince McMahon) won the fucking WWF title.
16.) RAW 4/13/98 - Vince McMahon vs. WWF Champion Stone Cold Steve Austin
Not really a match at all as much as a segment, but an entertaining and important one. This marks the first "official" Austin/McMahon showdown as well as McMahon's in-ring debut. It also marks Foley's heel turn and sets up the fun little feud he has with Austin as McMahon's in-ring proxy. Austin's got an arm tied behind his back for extra fun. And I'm pretty sure this is the spot where WCW's 84-week run of ratings dominance came to die.
17.) No Way Out 2001 - Stephanie McMahon vs. Trish Stratus
Considering there was no real veteran wrestler involved here to help offer guidance and structure, this match didn't turn out at all as bad as it by rights should've. Since it was on PPV, and since it was their first one-on-one encounter (at least that I can recall) I'm giving this the nod over their subsequent Whipping Match on RAW a couple months later.
18.) RAW 2/23/2004 - Vince McMahon vs. Eric Bischoff
Just because of the imagery... it finally happened! At least 3 years too late.
Shit... I need two more! Fuck it.
I'll figure it out later, or let the good folks of PW recommend some alterations and additions to the list above.