Here Comes The Money: Shane McMahon's Top 10 Craziest Moments

Image via Complex Original

Event: King of the Ring 2000

Why not start with Shane’s next opponent? Back in 2000, The Undertaker was running his American Badass character, which was...hit-or-miss. However, this six-man tag match (The Rock, Kane, and Undertaker vs. The McMahons and Triple H, for Haitch’s WWF Championship) definitely delivered, with a bunch of convoluted violence that led to the climactic flying chokeslam, from the top rope all the way down to the announcer’s tables. 

This was one of the first times where Shane was seen not just as an entitled rich kid, but someone willing to take the bumps to keep up (and surpass at times) the boys in the back. Looking back at it, the flying chokeslam seems almost tame with what Shane would eventually do; at the time, however, it was certifiably nuts that the heir to a billion dollar company would let one of its employees demolish him like this. We were so young and foolish then.

Event: No Way Out 2009

By 2009, Shane McMahon’s in-ring career was coming to its first close. His last feud was with the heel stable Legacy, and primarily with its leader Randy Orton, who at the time was known for viciously punting people into long hiatuses. The crown jewel of the feud was a No Holds Barred match with Shane at No Way Out 2009, a match that somehow is remembered despite being on the same show as the best Elimination Chamber match ever. It will become clear in this list that Shane is at his best when weapons and crazy spots are involved; after all, he was never a technically-proficient wrestler, so the addition of adrenaline-pumping violence evened the odds against some of the most legendary wrestlers of our time. 

This is Shane at his most beaten down, taking a massive amount of punishment not just from Orton, but from his cronies in Legacy (Cody Rhodes and Ted DiBiase, Jr.) for about 20 minutes, yet he won’t stay down. Chairs, kendo sticks, trash cans, and tables all flew around the ring with sickening thuds, yet the most heroic moment for Shane was an honest-to-goodness wrestling move, as he countered Orton’s punt into a (admittedly poor) spear. One could not be blamed for believing that Shane would win, but it was not to be, as Orton countered Shane’s own punt attempt into an RKO OUTTA NOWHERE (copyright: Michael Cole) for the win. While the feud would continue until Shane “broke” his leg and got written off for six years, it was this punishing match that was hailed as one of Shane-O-Mac’s finest performances top to bottom, with no hushed accusations of “he’s only a spot monkey” to bring it down.

Event: King of the Ring 1999

Stone Cold Steve Austin’s feud with the McMahons famously focused on Vince, and to good effect, but people often forget that Shane was involved in one of the bigger screwjobs of the era; at the Survivor Series Deadly Games tournament, Shane’s spot as a guest referee and confidant of Austin allowed him to double-cross the rattlesnake and eliminate him, blocking his attempt to be the WWF champion. Shane would intermittently pop up alongside his father to torment Austin, but the inter-generational feud would come to a head at King of the Ring 1999, where the McMahons would face off with Stone Cold in a handicap ladder match for control of the WWF. You can probably see where this is going.

Memorably, the stage setup had a crap-ton of ladders piled up, a fact that Stone Cold would use to his advantage in one of the key spots of the match, which saw him toss both McMahons into until the whole thing collapsed on their bodies. He would then throw Shane off a ladder onto a table (which doesn’t break) before jumping off and elbowing the Boy Wonder through the table (at which point it does break with a thud). A few more ladder shots to the face by Austin would disorient poor Shane, who at this point was not as well-versed in taking a huge amount of pain in as he would be later, yet via some ridiculous deus ex machina ending, it was Shane who would earn the glory of retrieving the briefcase at the top of the ladder, giving control of the WWF to his father.

Event: WrestleMania X-Seven

The Coast-to-Coast is one of the best remembered wrestling finishers of the Attitude Era, full stop. What would eventually be Shane’s in-ring calling card (most of his memorable spots happened outside of the ring, after all) debuted in a bloody and surprisingly competent Father vs. Son street fight at the greatest WrestleMania of all time, one that came shortly after the news that WCW had been bought out by...someone in WWF (more on that lower down the list). This match was pure McMahon bullshit in the best way, with all four core members (Vince, Stephanie, Shane, and Linda) playing a key role. Also, Mick Foley was the guest referee because why not. 

Shane’s two most memorable spots are radically different here: first, he attempts to put his father through the announcer’s table by leaping from the top rope down to the floor, but Stephanie moves the senior McMahon, causing Shane to crash through the table with no cushion. The second, however, is the one still played in highlight videos, as Shane beat his father into a corner before putting a trash can on his face. This set up the Coast-to-Coast, which saw Shane leap from the adjacent turnbuckle all the way across the ring, dropkicking the trash can into his father’s face and knocking him out for the 1, 2, 3. It was the first time Shane had done the move (at least in a real match and TV setting), and it would thankfully not be the last.

Event: Saturday Night’s Main Event 2006

Let’s get this out of the way: this match sucked. It was a glorified handicap match to try and get people excited about the doomed revival of Saturday Night’s Main Event, but it was just not doing it for anyone. Shame, really, because Shane McMahon in a street fight vs. Shawn Michaels with Vince McMahon terrorizing the Heartbreak Kid outside should make for, at least, a fun distraction. Alas, it was slowly paced and with some weak weapon shots, and ended with a reversal of the Montreal Screwjob that no one asked for. At least we got the spot of the night early on in the match in what became Shane’s last BIG bump (until WrestleMania this year, we hope): a superplex off a ladder in the ring down through two tables on the floor. 

Mind you, by this point, Shane had thrown himself off everything imaginable and endured legitimate amounts of pain from multiple hardcore matches, yet somehow this dude finds a way to keep his reputation intact. Watch the video again; there seems to be a slight moment of hesitation on the park of Michaels before he throws Shane over his head, crashing them both through the tables. One wonders what was said in that moment, aside from perhaps “this is going to hurt,” but it’s a small human moment in a cartoon-y match, and it makes the ensuing pain all the more real. Despite it being a throwaway main event on a throwaway show, Shane still put his body on the line four minutes into a match with the iconic Heartbreak Kid, partly to entertain and partly to show everyone that he’s got what it takes to be in the ring with a legend, technical skill be damned.

Event: Unforgiven 2003

The final leap of faith. Quick spoiler alert: this is the lesser of three similar spots, all of which appear in the top five of this list. By Unforgiven 2003, Shane McMahon had earned every single person’s respect with his death-defying leaps and willingness to break himself in half, so you can almost be (un)forgiven for seeing this and yawning. Then you realize you’re watching a man jump over 30 feet into what did not look like the softest crash pad in the world and you remember that death-defying stunts never get less impressive.

For what it’s worth, this entire match is pretty brutal and fell in the middle of a feud that also featured Kane electrocuting Shane’s testicles. Despite that hilarious(?) moment, 13 years later, the image that most people remember is Shane jumping into the great beyond, with Kane rolling out of the way to pick up a less-than-earned Last Man Standing victory. As of now, Shane would never leap off a similar height again...but WrestleMania awaits.

Event: SummerSlam 2000

The one that started it all. If the Unforgiven leap is the Grand Finale, then this is the euphoric beginning. When Shane won the Hardcore title from The Lethal Weapon Steve Blackman just days before SummerSlam 2000, he accomplished two very different things: 1) he won his second WWE title and 2) he pissed off Steve goddamn Blackman. There’s a reason the man is called The Lethal Weapon, after all. The martial arts master beat the everloving daylights of Shane during their hardcore match, which by itself was impressive enough...and then they started climbing.

Shane running away from Blackman by climbing up the Titantron was a stroke of heel genius, but it was the “oh my god he’s dead” fall that will live forever in the minds of WWE fans. 40-foot drop, and not even a leap; this was a dead drop after Blackman hit him in the back with one of his trademark kendo sticks. With one drop, Shane etched his legacy, or at least its beginning, into WWE history, and you can still see this drop in “craziest WWE moments” lists in every corner of the web.

Event: Monday Night Raw

In case you thought Shane was only a hardcore legend/spot monkey icon, he was involved in one of the most infamous angles of all time: The Invasion. Disregarding how horrendously botched the execution of the angle was, at the time of its conception, it seemed like it would engulf the entire industry. After all, WCW being bought out by WWE was big enough news, but when Shane-O-Mac himself announced that he had bought out WCW from under his father’s nose? That’s when the excitement really took over. 

First of all, it led to the excellent street fight covered in #7 on this list, which by itself makes it worth it. But it also established Shane as a shrewd businessman, one that could go toe-to-toe with his father. That was paid off multiple times during the Invasion angle, and hell, it even came into play on Monday night, 15 years later, as Shane outmanuevered Vince once more. That all began with 4 simple words on the last Monday Nitro, four words that changed the WWE forever (if not for the best): “I now own WCW!” 

Event: King of the Ring 2001

Ninety-nine percent of the time, if a botched move is remembered and discussed at length, it is because it was a mistake of colossal proportions. Think any time Sin Cara (either one) has messed up and injured himself over the last five years, for example. However, at King of the Ring 2001, a botched hardcore suplex became the ultimate display of batshit insanity on the part of Shane McMahon, by way of Kurt Angle. In what was already a pretty brutal street fight, the two men spilled to the outside and made their way up to the stage, where one particularly tough piece of glass was waiting. With Angle dominating this portion of the match (as he should, to be honest), the pair geared up for what was supposed to be the huge spot of the match: a suplex through the glass that would incapacitate Shane long enough to be dragged into the ring and pinned. The glass had other ideas, however.

Despite a massive suplex, Shane’s body did not go through the glass, resulting in a far more grizzly bump than expected; his head slammed against the glass and subsequently the floor, probably knocking him loopy for at least a moment. There’s a hilarious moment in the momentary terror that crosses both the ref’s and Angle’s face when they realize what happened, a moment that says “we are going to get SO fired.” And yet, not only was Shane ok, but with a quick moment of improv, he tells Angle to suplex him again in order to do the spot justice. The second time proved to be the charm, as Angle summoned his Olympic-sized strength and blasted Shane through the glass properly, turning Shane’s burgeoning hardcore reputation into legend.

Event: Backlash 2001

In 20 years, 30 years, 100 years, if the Earth isn't destroyed by wars and Trump presidencies, future generations will be able to find videos of Shane McMahon losing his goddamn mind and jumping 50 feet onto the Big Show. This is the climax not just of the match and the feud, but of Shane’s entire in-ring career. It’s not even a great leap; the move looks like it hurts him about 100 times more than it does Big Show, and even Test (rest in peace, you big Canadian) seems extremely worried that the boss’s son was maimed on his watch. It’s almost cringe-worthy to watch, even when you know that he ends up fine 15 years later. 

What makes it even better is that not only are you scared for Shane, but he is terrified for himself; watch him as he stares down and then crosses himself before leaping. It’s FASCINATING. Wrestlers are trained to show emotions only as the story dictates; if there is fear, well, it’s because a writer thinks a coward’s demeanor works best in that moment. But here, here was a man who was maybe out of his league and trying to compensate for his upbringing and his nepotism-aided spot, a man who was earning the right to be more than just a last name, and he went for it. For that, and for every other reason on this list, Shane McMahon holds a very special place in the hearts of wrestling fans. If you doubt his impact and his popularity, well...listen to Monday night’s cheers once more. Here comes the money, indeed.