Top 15 Most Terrifying Things Shane McMahon Has Ever Done

The WWE recently followed up a lackluster and predictable Fastlane pay-per-view with a loaded edition of Monday Night Raw that was highlighted by the return of Shane McMahon after a more than six year absence. Shane–O-Mac left the company near the end of 2009 to pursue other ventures and build a business legacy of his own and many people wondered if they would ever see him inside a WWE ring again. Well the Prodigal Son did return and he returned with a bang.

The episode of Raw kicked off with Vince McMahon heading to the ring to present the Vincent J. McMahon Legacy of Excellence Award to his daughter Stephanie when the segment was interrupted by a returning Shane who proclaimed that his sister did not deserve the award. Shane stated that he was sick of sitting on the sidelines and watching Stephanie and Triple H run Raw into the ground and claimed to have something to hold over his father's head. Vince told Shane he could have control of Raw, on one condition: He just has to win one match, against The Undertaker, at WrestleMania, inside Hell in a Cell.

Shane McMahon's return and his match with The Undertaker is a clearly transparent ploy to prop up a WrestleMania that is seriously lacking in star power due to a number of injuries to the company's biggest superstars.

Shane McMahon has won his place in the hearts of fans over the years primarily for his willingness to get in the ring and sacrifice his body in ways that no other WWE executive and few superstars ever would, providing us with some of wrestling's craziest moments.

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15 Shane Joins An Exclusive Club

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Beginning in 2001 the WWE would occasionally air a segment in which Vince McMahon would induct a superstar into the "Kiss My Ass Club". The superstar would have to pucker up and kiss Mr. McMahon's bare buttocks or risk hearing the words, "You're Fired". How the concept ever saw the light of day is mind boggling, but it did and continued to be used until 2008.

At WrestleMania 22, Vince attempted to induct Shawn Michaels into the club for a second time with the help of Shane, but the Heartbreak Kid countered and instead shoved Shane-O-Mac face first into his father's backside.

14 Austin Covers The McMahons In Ladders

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Shane McMahon started his WWE career as a referee and announcer before being prominently featured in storylines during the Stone Cold vs. Mr. McMahon feud. Shane defied his father by signing Austin to a contract and then double-crossed the Texas Rattlesnake as a referee during the Deadly Games tournament at Survivor Series in 1998. This led to a McMahons vs. Austin ladder match for control of the company at the 1999 King of the Ring. The bout's key spot featured Austin throwing the McMahons into a number of ladders that had been set up at the entrance and then pulling a support piece causing roughly ten ladders to collapse on top of Vince and Shane.

13 Getting Superplexed Off The Top Of A Ladder Through Two Tables

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In 2006 the WWE attempted to resurrect Saturday Night's Main Event, an endeavor that would eventually fail. The first episode of the revival featured a street fight between Shane McMahon and Shawn Michaels. The match itself wasn't great and it ended with an unnecessary and poorly executed replication of the Montreal Screwjob with the Heartbreak Kid on the opposite side this time, but the bout did feature one impressive high spot: Michaels superplexing Shane off the top of a ladder to the outside of the ring, through two tables. It wasn't the biggest bump of Shane's career, but it was the last major one he took before his departure.

12 Leap off the Cage

This will look quite tamed next to the entries to come, but this is just more proof of how fearless Shane was when working for WWE. In no way did he ever have to take an enormous bump or take big risks, but whether it was a big PPV match, or a simple run-in like this, Shane delivered. With Shane having now given Test his blessing to marry his sister Stephanie, Shane had ordered his Mean Street Posse off of the couple, but they wouldn't comply, turning Shane face in the process. With Test being beaten down by Shane's old crew, the Boy Wonder took matters into his own hands, jumping off the cage into his former friends.

11 The Leap Of Faith

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In 1999 Shane was involved in a feud with Stephanie McMahon's boyfriend, Test. The Boy Wonder did not want his sister dating Test and the feud culminated in a "Love her or leave her Greenwich Street Fight” at SummerSlam. The stipulation for the match being that Test would have to dump Stephanie if he lost and would receive Shane's blessing if he won. Test won the bout, but the match was first real glimpse we got of Shane's affinity for high risk maneuvers. He executed an elbow drop from the top rope to put Test through the Spanish announce table, a move that would become known as the Leap of Faith.

10 Being Chokeslammed Through A Table

SummerSlam 1999 may have been where we first got a taste of Shane's willingness to jump from high places, but the 2000 King of the Ring was where we first witnessed him allowing others to involve him in high spots. Shane McMahon teamed up at the event with his father Vince and Triple H to take on Stone Cold Steve Austin, the Rock, and the Undertaker in a six man tag match for the WWF Championship. During the match, Shane received a flying chokeslam, from the top rope through the announce table, courtesy of his WrestleMania 32 opponent, the Undertaker.

9 Getting Electrocuted By Kane

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In 2003 Kane removed his mask for the first time and became a much angrier and unstable monster - you may recall him setting Jim Ross on fire. Kane embarked on a bitter feud with Shane McMahon after the Big Red Monster delivered a tombstone piledriver to Shane's mother, Linda. This feud would feature a few of Shane's craziest moments. On one episode of Monday Night Raw, Kane attacked Shane-O-Mac, tied him to the outside of the turnbuckle, then took a battery from underneath the ring and proceeded to electrocute Shane's genitals. Rob Van Dam eventually intervened and Shane-O-Mac was taken out of the arena on a stretcher.

8 Pushing Kane Into A Fire

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Another big moment of the feud between the Demon Seed and the Devil's Favorite Demon occurred during a match between Shane McMahon and Chris Jericho on Monday Night Raw. Kane interrupted the match to attack Shane and the two battled back and forth, eventually making their way to the backstage area where the Big Red Monster poured gasoline into a dumpster before setting it ablaze. He then picked up Shan-O-Mac and tried to throw him into the flaming dumpster, but Shane reversed the maneuver and instead kicked Kane into the fire, before uttering, "Burn in hell, you son of a b***h".

7 Jumping Off An Ambulance

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Shane McMahon's feud with Kane culminated with a Last Man Standing match at Unforgiven followed by the first ever ambulance match at Survivor Series. The object of the latter bout was to beat your opponent to the point that you could put him into the back of the ambulance and close the doors. During the match, Shane executed his signature coast to coast maneuver by jumping off the top of the ambulance into a trash can placed in front of Kane's face.

This wasn't the first time Shane pulled off the move and given that he landed safely on a box that appeared to be made out of cardboard, it didn't look like the most daring time attempt either, but it was the only coast to coast to occur from atop an emergency vehicle.

6 Beating Down Randy Orton

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Shane's last major feud before his departure came with Randy Orton in 2009. After Orton had punted Vince McMahon in the head, Shane came to his family's defense, leading to a No Holds Barred Match at No Way Out. For roughly twenty minutes, Shane was beaten with kendo sticks, trash cans, tables, and chairs by Orton and his Legacy comrades, but refused to stay down. Shane-O-Mac eventually attempted a punt of his own, but had the move reversed into a match ending RKO. He received a punt to the head from Orton the following night on Raw and although he would later return, he was eventually written off of television with a broken ankle.

5 Coast To Coast

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WrestleMania X-Seven was arguably the greatest 'Mania in history. The event featured a title match between Stone Cold Steve Austin and The Rock, the second ever TLC match, a Triple H vs. The Undertaker match, and a father vs. son match pitting Shane McMahon against Vince in a street fight. The pivotal point in the match came when Linda McMahon awoke from her coma to kick her husband in the "McMahon family jewels". Special guest referee Mick Foley then put a beat down on Vince McMahon to set Shane up for his WrestleMania moment.

With Vince sitting in the corner with a trash can in his face, Shane climbed to the top of the opposing turnbuckle and jumped coast to coast to kick the trash can into his father's face before pinning him for the 1-2-3. The signature move would continued to be used by Shane throughout the next few years, but the WrestleMania X-Seven version is the one we'll always remember.

4 Shane Jumps Off The Titantron, Part Two

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As previously mentioned, during the 2003 feud with Kane, Shane battled him in a last man standing match at Unforgiven. The two fought their way up the ramp and Shane eventually beat Kane down on the stage and then began climbing up the Titantron. As he reached the top, Jim Ross emphatically and repeatedly screamed, "Don't do it kid! You've got too much to live for!" Shane then jumped from atop the Titantron through the stage below as Kane rolled out of the way and eventually got his feet to pick up the win. By this time fans had become accustomed to watching Shane McMahon jump from high places, so this Leap of Faith didn't seem as crazy as past versions.

3 Shane's First Jump Off The Titantron

At the 2001 Backlash pay-per-view, Shane McMahon battled the Big Show in a Last Man Standing match, and got some assistance throughout the bout from his former rival, Test. As the competitors made their way out of the ring and up the ramp, Big Show chased after Shane with a pipe, causing him to scurry up to the top of the stage set to escape. Test then beat down the Big Show, setting him up for the Leap of Faith from Shane from atop the set. Shane hit the move and put the two competitors throw the top of the stage. Test then cleverly used a nearby camera crane to help Shane get to his feet and beat the ten count.

2 The 50 Foot Drop

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Shane McMahon's multiple jumps off Titantrons were impressive, but his legacy of descending from high places all began at SummerSlam 2000. Shane had beaten Steve Blackman for the Hardcore title a few days earlier and the two met for a rematch at the biggest event of the summer. During the hardcore bout, Blackman chased Shane up to the top of the SummerSlam set with a kendo stick. The Lethal Weapon followed Shane up the set and after multiple lashes to the back with the kendo stick, Shane then dropped straight backwards, roughly 50 feet to the stage below. Blackman then jumped from the stage onto Shane to pick up the pin and the victory.

1 Kurt Angle Drops Shane On His Head

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We've seen Shane McMahon dive through tables, jump off an ambulance, and drop 40 feet, but the biggest bump of his career came at the 2001 King of the Ring. Shane-O Mac was involved in a street-fight with Kurt Angle that featured many hardcore moments. Midway through the match the two combatants made their way up the ramp and towards the stage. Shane delivered a suplex to Angle on the ramp floor that left the Olympic gold medalist with a chipped tailbone. Shortly thereafter, a spot in the match called for Angle to deliver and belly to belly suplex to Shane and put him through the stage glass. However, Angle didn't have the strength to deliver the maneuver with full force. The glass failed to shatter and Shane landed on his head on the cement floor. He lied there for just a few seconds before Angle repeated the maneuver, this time successfully shattering the glass. When it came time for Angle to put Shane through the glass from the other side, the glass failed to break again and eventually Angle opted to throw Shane head first through the glass.

Since their infamous bout, Angle has said in multiple interviews that the set was supposed to contain sugar glass, a type of stunt glass so fragile that no pyrotechnics were used that night out of fear of breaking it, but someone accidentally ordered plexiglass instead. That mistake ended up putting both Kurt Angle and Shane McMahon in the hospital that night and provided the craziest moment of Shane's career.

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