The list of people who Shawn Michaels inspired to become wrestlers is endless. Although HBK's career in the 2000s was enough to justify his place in the WWE Hall of Fame, Shawn Michaels in the 90s was arguably the most entertaining wrestler of an era that included Hollywood Hogan, Sting, and Stone Cold Steve Austin.
"The Heartbreak Kid" didn't become Mr. Wrestlemania or the icon he is by not having great feuds. Yes, his storylines with John Cena and Kurt Angle are definitely on the list of greatest feuds of Shawn Michaels' career. This list, however, will examine the greatest feuds of Shawn Michaels' career in the 1990s. This was the era of the Monday Night Wars, bloody chair shots, and a "heartbreak kid" who fans couldn't help but obsess over.
10 The British Bulldog
The British Bulldog was one of the first solo feuds of Shawn Michaels' career after his time with The Rockers. Davey Boy was the first person Shawn Michaels ever defended the Intercontinental Title against. The two put on great matches and had a ton of chemistry.
Michaels and Bulldog also clashed later for the WWF European Title in the late 90s. Their WWF World Heavyweight feud was also an insane storyline where Michaels was accused of making advances at Bulldog's wife. Bulldog was ultimately unable to take the title from "Heartbreak Kid."
9 Vader
Although Michaels and Vader clashed many times in the 90s, SummerSlam 1996 was all it took for their feud to become iconic. This story was big because of the issues the pair had both inside and outside of the ring. The feud with Vader showed him defeating Shawn Michaels twice, but never being awarded the title since the matches were won via count out and DQ.
At SummerSlam 1996, rumblings about the two having heat outside of the ring added to the fire that already burned heavy thanks to their great feud. In the match, Michaels was visibly upset with Vader and screamed at him. Although they would battle a few times after SummerSlam, it was the peak of their great feud.
8 Sycho Sid
This rivalry is severely underrated by many. The only reason many fans don't remember much about this feud is because Michaels has way too many memorable moments in the era surrounding his storyline with Sid. He was originally Michaels' new bodyguard after Diesel and Shawn split up.
Sid and Michaels would feud after Sid turned on him and after a quick departure from the WWE returned to face Michaels for the WWE title at Survivor Series 1996. The two also battled for the title in Michaels' home state at the Royal Rumble 1997. The feud featured one of the first (now trite) contracts signing segments and ended when Michaels retained the title, but "lost his smile."
7 Mankind
This feud would be top five for HBK in the 90s if it lasted longer. There were no characters more different in the 90s than Shawn Michaels and Mankind. One was a narcissistic monster, the other was a reclusive outcast. Mankind tried to manipulate Michaels but failed to get into his head saying HBK had too little going on up there to manipulate.
It was also one of Mankind's enemies that wasn't a giant. It appeared he could beat Michaels, which added a ton of stakes to their story. Their near thirty-minute bout at WWF In Your House 10: Mind Games is one of the best of both of their careers.
6 Diesel
One of the most important wrestling figures Michaels helped introduce to the world of wrestling was Kevin Nash, Diesel in the WWE. Today, most fans think of them as best buddies and members of the Kliq. There actually was a ton of story between the two future mega-stars. "Two Dudes with Attitudes" won the tag team titles and it was clear Diesel was also a star.
The two ended up competing at WrestleMania XI against each other. Diesel had his last match in the WWE against Michaels ending his feud with the man who helped establish him before he left for WCW and established the NWO (the real one, not the one Michaels joined in 2002).
5 The Undertaker
Although younger fans may only remember their impeccable WrestleMania matches from later in their career, Michaels vs Undertaker was one of the best 90s rivalries. After costing The Undertaker the title at SummerSlam 1997, The Deadman set his sights on HBK.
Michaels started the feud running away from Undertaker, which lead to the first Hell in a Cell match at In Your House: Badd Blood. This feud also led to the introduction of Kane. Their casket match at Royal Rumble 1998 put an end to a great rivalry that, like Undertaker, was far from dead in the 90s.
4 Marty Jannetty
Michaels was introduced to wrestling audiences as one half of "The Rockers" with Marty Jannetty. The two never officially earned the WWE tag titles but did make a big splash early on. Ironically, the feud between these two is far more memorable than their tag team success.
After Shawn Michaels turned on Jannetty, he essentially started the character that would become the "heartbreak kid." Although Michaels was a heel, fans couldn't help, but cheer for him. He feuded with Jannetty in some underrated matches and Marty Jannetty was the first person to ever win a title on an episode of Raw when he defeated HBK to earn the IC title in 1993.
3 Razor Ramon
"The Bad Guy" Razor Ramon and Shawn Michaels had, arguably, the greatest Intercontinental Championship feud of all time. These battles were truly greater than many of the world title battles of this era. Their ladder matches will always be revisited by wrestling fans and after their 1995 story, the two became huge superstars.
There are only a handful of feuds that will instantly take fans back to the 90s and this is one of them. It was two overconfident stars who could perform well with anyone in the ring. HBK and Razor's chemistry was undeniable. Their promos were hilarious and without this feud, neither Hall of Fame legacy would be the same.
2 "Stone Cold" Steve Austin
WrestleMania 14 is one of the most important battles in the history of wrestling. The second that Stone Cold stunned Shawn Michaels the wrestling world would never be the same. The lead-up to this battle was two careers in the making and it is undoubtedly one of the biggest moments of Shawn Michaels and Steve Austin's careers.
Michaels and D-Generation X were the precursors to the rise of Austin. Although Michaels was a heel, he was also beloved by a ton of fans. The feud with "Stone Cold" was supposed to be the usual "face vs heel" battle, but ended up being an "interesting character vs interesting character" and that was a crucial piece of evolution for wrestling. The feud also helped make WWE a house name and was a passing of the torch feud full of great moments including the addition of the "baddest man on the planet", Mike Tyson.
1 Bret Hart
Batman has the Joker, Superman has Lex Luther, and in the 90s, Bret Hart had Shawn Michaels. Many argue that "Hart vs Michaels" is not only the best feud of the 90s but also the greatest wrestling feud of all time. The amount of iconic moments between the two of them is endless.
At its core, this feud is great, because it was the ultimate new generation vs old generation story. Hart was the more traditional wrestling star, while Michaels was changing the game. Fans will always be on either side of a generational argument. Their matches were also always explosive and a reflection of their personal drama. These two men helped build the WWE to what it is today and few have ever had a feud that could touch "Hart vs Michaels" in the 90s.