Professional wrestling fans around the world were legitimately stunned when Shane McMahon returned to World Wrestling Entertainment in February 2016 to become an on-air character once again. Those of us who are not working in the WWE cannot say for sure how long McMahon will be around, but it has been announced that the son of Vince McMahon is scheduled to have a Hell in a Cell match versus The Undertaker at WrestleMania 32. There is, as of early March, still time for the WWE to swap McMahon out of that match, but all indications seem to point to McMahon facing off with 'Taker at the biggest show of the year.
McMahon is, as diehard WWE fans know, not a stranger to the ring even though he has been away from the WWE for many years. The son of the WWE CEO earned a reputation for taking crazy bumps that men who are revered as tremendous athletes and great wrestlers have stayed away from during their careers. While McMahon is not one of the best workers of his time, he has been part of some memorable matches, including one of the greatest King of the Ring contests in history. McMahon definitely paid the price and put his body through hell on that night.
10 The WWF vs The Alliance: Survivor Series 2001
Ignore the fact that Shane McMahon was eliminated from this Survivor Series match in 15 minutes, and also forget about the awful storyline that was being buried for good on this night. The arrogant McMahon eating a choke slam from Kane, a tombstone from Undertaker and the “Lionsault” from Chris Jericho before being pinned was the perfect way for the character to be taken out of the contest. While the majority of the year had been disappointing for fans, this match was worth the money. It's too bad that the WWF got things so wrong and wasted what should have been a can't-miss storyline.
9 Shane McMahon vs Kane: Unforgiven 2003
We are not going to pretend that the feud involving Shane McMahon and Kane did not have some terrible writing. McMahon and Kane did, however, put on a good match at the 2003 edition of Unforgiven. The match took place under “Last Man Standing” rules, and thus there were plenty of smoke and mirrors to assist the two performers. McMahon even went back in time, in a way, when he plummeted to his doom from the Titantron for the second time of his career. We hope that Shane is not, in 2016, hoping to recreate such stunts at any point in the future.
8 Shane McMahon vs Big Show: Backlash 2001
Let's be clear about the fact that the Last Man Standing match that featured Shane McMahon and Big Show was ridiculous in several ways. McMahon, the babyface in this scenario, received all kinds of help from Test, to the point that the contest would have ended in a draw if not for Test's assistance. Shane was known by fans as a glorified stuntman, and he did not fail to deliver when he performed his “Leap of Faith” to the delight of the audience. The writing made sense for the story that the WWE was trying to tell, although McMahon would be turned heel not long after this contest.
7 Shane McMahon vs Steve Blackman: SummerSlam 2000
Let's be honest and just point out right away that the reason we remember this Shane McMahon versus Steve Blackman encounter is because of the crazy bump that McMahon took near the end of the contest. McMahon found out that climbing up the Titantron during a match was a mistake, as Blackman caused Shane to fall (allegedly) 40 feet after hitting McMahon with a kendo stick multiple times. Any highlights of the “Attitude Era” that you see probably include this moment, and for good reason. It showed just how far McMahon would go to entertain audiences.
6 Shane McMahon vs Randy Orton: Now Way Out 2009
Shane McMahon turning babyface to feud with Randy Orton in 2009 was an awful decision for several reasons, but it at least gave us an entertaining match between the two at No Way Out. The two made the best of some horrible booking, as Orton bled early on and did his best to help make Shane look like a real threat. Shane was also on the receiving end of his fair share of punishment, and his sell of the RKO at the end of the match is glorious to behold to this day. Remember this as a one-off match and not as part of a terrible feud, and you may enjoy re-watching it more.
5 Shane McMahon vs Test: SummerSlam 1999
Only in pro wrestling can a promoter book a match in which one man's sister and a different man's girlfriend is on the line in a “Love Her or Leave Her” encounter. Both Test and Shane McMahon were green when they met up for this showdown that was “for” Stephanie McMahon, but one could already tell that both were capable of doing special things later in their careers. Truth be told, this would go down as one of Test's best matches while working in the WWE. The right man got his hand raised on that night, as Test defeated Shane to give a nice celebration for romantics everywhere.
4 Shane McMahon, Vince McMahon and Big Show vs D-Generation-X: Unforgiven 2006
What you will tolerate and what you like to see in pro wrestling matches probably affected what you thought of this encounter. The McMahons teamed up with the Big Show to face off with Shawn Michaels and Triple H inside of Hell in a Cell at the 2006 edition of Unforgiven, and the match was an intriguing blend of brutality and humor. Yes, for those of you trying to recall, this is the match where Vince's head met up with a certain part of Big Show's body. Go back and watch via the WWE Network or by other means to re-live this moment.
3 Shane McMahon vs Shawn Michaels: Saturday Night's Main Event 2006
The story that involved Shane and Vince McMahon feuding with Shawn Michaels and also God (don't ask) included some bad writing and some terrible skits. It also gave fans several entertaining matches. Shane and Michaels went at it on national television during an edition of Saturday Night's Main Event, and they put on an entertaining contest that included a shout-out to the past. The battle ended in controversy when Vince called for the bell after Shane locked Michaels into the Sharpshooter, a replay of the infamous “Montreal Screwjob.” No offense to Shane, but it didn't hurt that he was working with one of the greatest wrestlers of all time on this particular night.
2 Shane McMahon vs Vince McMahon: WrestleMania X-7
2001 was a horrible year for the WWE and for the pro wrestling industry in general. World Championship Wrestling closed its doors, and the WWE wasted the “Invasion” storyline with some of the worst writing to ever happen in a wrestling company. WrestleMania X-7 was a highlight of the year, however, so much so that some would still claim that it is the greatest WrestleMania in history. Shane McMahon and Vince McMahon battled it out in a street fight at this WrestleMania, and Shane walked away as the winner following a Coast-to-Coast dropkick that has to be seen to be truly appreciated.
1 Shane McMahon vs Kurt Angle: King of the Ring 2001
It was the kind of match that you will likely never again see in the WWE – at least you won't during the company's PG Era – because of how truly violent it was. Kurt Angle and Shane McMahon told a tremendous story during their encounter at the King of the Ring, and that tale included McMahon being legitimately bounced off of his head on multiple occasions. The truth of the matter is that the WWE is lucky that both McMahon and Angle were able to get through the match without suffering a serious injury. Knowing that they both lived to tell about it afterward helps make re-watching that match enjoyable.