The 1990s saw a lot of change for the WWE, going from the Golden Era to the New Generation Era to the Attitude Era, and with that saw a sea of different major stars and huge moments each year. WWE didn’t run as many shows in the early 1990s so the chance of “shocking” things were less, but as the decade went on it became much harder to pick between particular moments.
There were many shocking moments, though they came in different forms. Some of these were in the form of match results, returns, and sometimes even horrendous booking decisions that were just so shockingly bad that they have to be included here.
10 1990: Ultimate Warrior Shocks Hulk Hogan
By the time 1990 rolled around, Hulk Hogan was the biggest star in professional wrestling and at the tippy top of the mountain in WWE. Seeing him lose, and lose clean for that matter, was a rarity and almost an impossibility by this point.
At WrestleMania 6, Hogan took on fellow super babyface The Ultimate Warrior, who had received a huge surge in popularity over the previous years. They battled in the main event, and in a complete shock and surprise, Warrior not only won, but he did it clean. Warrior ended WrestleMania with an unprecedented win over the top star as both Intercontinental and WWE Champion.
9 1991: Randy Savage Forced To Retire
Randy Savage had been one of the biggest names outside of Hulk Hogan in the late 1980s and early 1990s in WWE, but in 1991 the WWE fans were shocked when he lost a match at WrestleMania to Ultimate Warrior and was forced to retire, particularly because he was still at the top of his game.
This “retirement” also saw the shocking moment in which Savage reunited with Miss Elizabeth after the match in an emotional moment which is among the most memorable in WrestleMania history.
8 1992: The Ultimate Warrior Returns
WrestleMania 8’s main event was a plodding affair in which Hulk Hogan and Sid Justice slogged through their match. The ending was infamously botched, with Papa Shango missing his cue. The match ended in a DQ, with the two heels beating down Hogan.
Ultimate Warrior’s music would hit after months of being away from the promotion with no sign of a return in sight. The fans went into a frenzy at this unannounced and unexpected appearance from the beloved star.
7 1993: Hulk Hogan Leaves WWE
For years, Hulk Hogan had been pushed as the biggest name in WWE. In 1993, he shockingly parted ways with the company and signed with WCW. Of course, this wasn’t an on-screen moment, but it was still something which rocked the core of professional wrestling.
Hogan would ruin the main event of WrestleMania 9, winning the WWE Title before then dropping it back to Yokozuna, ending his run with the company on his back as he went over to begin a new era in WCW.
6 1994: Shawn Michaels Jumps Off The Ladder
In 1994, arguably the most shocking moment of the year came with a spot in the Shawn Michaels vs. Razor Ramon ladder match at WrestleMania 10. This show saw several big moments, but the unprecedented moment of Michaels jumping off a ladder was something WWE fans had never seen before.
Going in, it wasn’t entirely clear how this sort of match would play out, but Michaels and Ramon helped to make history by using the ladder in a variety of creative ways which shocked the audience.
5 1995: Shawn Michaels Wins From Number One
The Royal Rumble match was steadily becoming a highly anticipated part of WWE’s calendar year by the time 1995 rolled around, but fans had never seen someone go from number one to win the match.
The 1995 match saw Shawn Michaels enter the match in the number one position and go on to win the whole thing. The way it was done was ingenious, with everything thinking Michaels was eliminated, though only one foot hit the floor. This made his return into the ring and dumping out the British Bulldog all the more shocking and impactful.
4 1996: Brian Pillman’s Got A Gun
In 1996, Brian Pillman was involved in a storyline with Steve Austin, and on an episode of Monday Night Raw one of the most shocking and horrific moments in WWE history took place.
During a segment at Pillman’s home, Pillman pulled out a gun and pointed it at his rival, before the feed cut to black. This was a very intense, surreal, and extreme angle, a like of which fans had never seen before in WWE. It was a shocking moment in all the wrong ways.
3 1997: Montreal Screwjob
There is no question to what the most shocking WWE moment of the year was in 1997, and it was arguably even the most shocking of the whole decade. With Bret Hart on his way out of WWE, he didn’t want to put over his real life rival Shawn Michaels on the way out. This led to Vince McMahon concocting a plan.
In the Survivor Series main event, a shoot finish was called to take the WWE Championship off Bret Hart without his prior knowledge. This caused a load of chaos in the ring, and it brought Hart’s time in the company to a very sour end.
2 1998: Mankind Thrown Off The Cell
The Undertaker battled Mankind at King of the Ring 1998 in perhaps the most iconic match in WWE history. It wasn’t a technical masterclass but it was a spectacle due to the shocking moment (or moments) where Mankind was thrown off the top of the Cell, crashing through the announce table. This was followed up with a chokeslam through the roof and down to the ring below.
Spots like this had never been seen before in WWE, and the sheer risk factor behind it made them extremely shocking to witness.
1 1999: Stephanie McMahon Turns Heel
Stephanie McMahon had been mostly the sweet and innocent babyface daughter of Vince McMahon, and often played the damsel in distress. At the back end of 1999, Triple H and Vince were feuding, and had a match at Armageddon.
At the end of the match, it was revealed that Stephanie and Triple H had been in cahoots throughout the whole storyline. Stephanie turned heel in a shocking moment, creating the McMahon-Helmsley partnership which would rule WWE for decades.