Shawn Michaels is considered by many to be the greatest wrestler of all time when it comes down to overall performance in the ring. Michaels ushered the WWE into a new era away from the Hulk Hogan and Ultimate Warrior world of slow paced bodybuilders and used more of a flashy style implementing high flying moves and technical wrestling. Michaels would create a library of memorable matches, spectacular moments and one of the most special careers anyone has achieved in the WWE. When you think about the most important wrestlers in the WWE’s history, Michaels would be at the top of the list.
Looking at today’s WWE roster and the overall wrestling world, you can see Michaels has inspired a new generation of stars to evolve wrestling into a more athletic oriented business where the talent focuses more on work rate than getting through an easy match. Many of today’s stars name Michaels when asked who their dream opponent would be. Wrestlers such as Seth Rollins, Daniel Bryan, Kevin Owens and more have gone on the record to say that’s the one person they would want to work with in a dream world and it’s for good reason. The Heartbreak Kid is nearly untouchable when it comes to having a stellar big match, regardless of his opponent.
Unfortunately with Michaels’ best years taking place in two distinct time periods and for one wrestling company, it left many great matches impossible to happen. Michaels was one of the few main event stars of the 90s to never jump ship to WCW, so there were a lot of great talent there he never faced. The same can be said for the new stars in the WWE as many of the top talent today would have been perfect for Michaels to work with but he retired just before the new batch of fresh names emerged on the WWE roster. Some of these matches may have taken place on house shows or in dark matches but never happened for the majority of fans to see.
15 Seth Rollins
The debut of The Shield in WWE was the most successful introduction to new talent in years, as all three men have become stars for the company. Of the trio, Seth Rollins has established himself as a main event act and one of the elite workers in the company. The comparisons are there to Shawn Michaels who became a star in similar fashion after leaving The Rockers. Aside from the similar styles and career paths, the two would create magic in the ring together as both know how to play the face and heel roles perfectly to get the best out of any match they’re in.
14 The Ultimate Warrior
The Ultimate Warrior was one of the most popular superstars of his era and returned to WWE during the peak of Shawn Michaels run as the top babyface star in the mid-90s. While Warrior was extremely limited in the ring, his best work was against elite in-ring workers like Randy Savage and Rick Rude, so seeing him mesh against Michaels would have been quite interesting. Michaels was gaining a reputation at the time for carrying the more physically impressive men to their best matches and he likely would have done the same for Warriors by bumping his ass off. Even if he couldn’t carry Warrior, a match between the two still would have been must see to watch a battle between icons of different generations.
13 Dean Malenko
An underrated aspect to Shawn Michaels career was seeing him in the Intercontinental Championship picture in the mid-90s, which gave us great matches with Jeff Jarrett, Owen Hart and standout midcarders. A little while later, WCW had the greatest undercard depth wrestling has ever seen during the Monday Night Wars and one of the best talents there was Dean Malenko. Much like Michaels, Malenko was a near guarantee for a great match due to his in-ring skills. Michaels ended up facing most of the elite WCW talent like Chris Jericho and Rey Mysterio when they became stars in WWE but Malenko didn’t become a star and ended his in-ring career before Michaels returned in 2002. A match between the two would have stolen any show it appeared on.
12 Bam Bam Bigelow
Shawn Michaels would always get the best out of his opponent, especially against larger wrestlers like Kevin Nash, Sycho Sid and Vader. Michaels was a superb bumper and seller so the giants would look legitimate while Michaels' high risk moves would make more sense and look more impressive against them. One of the best big men in the business was Bam Bam Bigelow, but he never worked in a singles program with Michaels. There’s no doubt these two would have had great chemistry with Michaels playing a perfect face to Bigelow’s heel. If this happened, Bigelow likely would have had a more successful and longer tenure in WWE.
11 Rick Rude
It’s quite surprising these two never crossed paths when Rick Rude was a wrestler as the two are at the top of the list from the late 80s/early 90s elite workers. Shawn Michaels was more skilled in flying around the ring and getting the energy of the crowd up while Rude was a master at controlling the crowd while slowing down the pace in a compelling way. The two would work together in D-Generation X after Rude retired from wrestling matches. Rude was basically a bodyguard for Michaels and the rest of DX when the group started and it’s just another reminder how much it sucked that we never got a match between the two top talents.
10 A.J. Styles
When Shawn Michaels returned to WWE from 2002 to 2010 and become the top wrestler in the company, TNA became a new viable wrestling promotion to work for and its brightest star was A.J. Styles. Doing things in the ring that had never been seen before, Styles was one of the most exciting wrestlers in the world and was on the short list of wrestlers matching Michaels body of work during those eight years. Sadly, Styles never defected to WWE during that time frame, as he’d have had a stellar match with Michaels and many others in the company.
9 Dolph Ziggler
One of the current wrestlers that draws comparisons to Shawn Michaels is Dolph Ziggler due to his immaculate selling and exciting in-ring style. The WWE careers of both men overlapped but we never got the pleasure to see them wrestle against each other in a singles match. Ziggler’s career has been on the decline due to many factors, including never getting a chance to shine in the big match against the ideal opponent. If Michaels worked a program with him before retiring, it could have provided what Ziggler is missing, helped him grow as a performer and given us a tremendous wrestling match.
8 Ricky Steamboat
Very similar to Shawn Michaels, Ricky Steamboat was a wrestler everyone wanted to work with because they know they would have their best match against him. Steamboat was before his time as an elite worker and one of the greatest pure wrestling talents the industry had ever seen. If Steamboat didn’t go to WCW in the early 90s, we may have been treated to a match with Michaels. There’s no scenario in which a spotlighted match between Michaels and Steamboat would have not resulted in a classic that we'd still talk about today.
7 Randy Savage
A match between these two did take place during a UK tour and was released on home video, but it wasn’t on television or PPV. According to Randy Savage’s brother Lanny Poffo, Savage wanted to work a program with Shawn Michaels going into a WrestleMania match, seeing his potential and an opportunity to create something special. WWE was trying to push Savage away from the ring as a commentator so it never happened and Savage went to WCW. Most wrestling lists would place these two in the top 10 all-time best talents, so it’s incredibly disappointing that we never got to see a program between them.
6 Eddie Guerrero
There were a lot of parallels between the careers of Shawn Michaels and Eddie Guerrero. Both were immense talents with personal demons that were exiled when they found faith and turned their careers around for the better. Michaels vs. Guerrero was apparently in the plans for a big WrestleMania 22 attraction match billing the two former heartthrobs but Guerrero passed away a few months before the show. Considering how both Michaels and Guerrero were performing at extremely high levels at the time, especially in big WrestleMania matches, they would have put out a “Match of the Year” candidate and provided a special night.
5 CM Punk
Despite working together in WWE for over three years, CM Punk and Shawn Michaels never faced off in a singles match. The biggest negative of the brand split was that it prevented top wrestlers from facing each other unless it was a special occasion like a WrestleMania match. Regardless, it was a huge missed opportunity by not going with a heel CM Punk vs. legend Shawn Michaels before the latter retired and the former walked away.
4 Brock Lesnar
Shawn Michaels' return to WWE and Brock Lesnar’s first title win both happened on the same night at SummerSlam 2002, but it was the closest thing to interaction between the two during Brock’s first run with the company. Michaels was a Raw wrestler and Lesnar spent all of his time on SmackDown before leaving the company two years later. When Lesnar returned to the WWE, Michaels was already retired but they had in ring interaction during Brock’s feud with Triple H. Michaels vs. the most credible monster wrestler in WWE history would have played to both of their strong suits perfectly.
Sting was the icon of WCW. Shawn Michaels was the icon of WWE. Sadly this stopped the two legends from ever having a match against each other. Sting sticking with TNA for so long likely was the biggest factor in blocking any final chance at this, as when he finally debuted in WWE last year, Michaels was long gone. We did see them interaction at WrestleMania 31, as Michaels attempted to help Triple H defeat Sting, though it was the cruelest tease of how magnificent this could have been in the 90s. The popular opinion is Sting’s WWE dream match would have been with The Undertaker due to the spectacle, but Sting vs. Shawn Michaels would have been the better match.
2 Daniel Bryan
With the easiest storyline available, Shawn Michaels originally trained Daniel Bryan as Bryan entered the wrestling industry. Many years later, Bryan became one of the most popular stars in the WWE with a wrestling style very reminiscent to Michaels. The two had their first on-air moments together when Bryan was feuding with Triple H and The Authority. Michaels cost Bryan a title match which led to Bryan putting Michaels in his Yes Lock submission the following night. This gave fans false hope that Michaels would return to the ring at WrestleMania to face his former student, but Michaels remained adamant he would never wrestle again.
1 The Rock
Given how important both men were to the WWE at around the same time, it’s nearly impossible to believe The Rock and Shawn Michaels never faced off. Bret Hart tells a story in his book that Triple H and Michaels used to attempt to bury The Rock during his early days in WWE, seeing him as a threat to their stranglehold of power. This led to rumors of The Rock never wanting to work with Michaels once he became a star that could call his own shots. The match would have been perfect around 2002-2004 when Michaels was an active competitor again and The Rock would make the occasional big match return. The storyline, promos and big match at a WrestleMania could have led to lots of money and positive fan memories.
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