5 Superstars That Shawn Michaels Loved Working With (& 5 He Struggled With)
Michael Hansen 
It's been said that Shawn Michaels is so talented in the ring that he can work a match with a broomstick. While there are no reports of the Heartbreak Kid having complex relationships with cleaning equipment, there are many accounts of his chemistry (or lack thereof) with opponents across his 25-year career.
Shawn Michaels' 10 Biggest Rivals (& Their Best Match Together)
What were Shawn Michaels' best matches with each of his 10 greatest WWE opponents?In the case of some HBK dance partners, there was an evident lack of fit in terms of personality or in-ring caliber. Other opponents, meanwhile, worked impeccably with Michaels to put on memorable performances.
10 LOVED WORKING WITH: Owen Hart
HBK Had A Blast With The King Of Harts
While wrestling fans are extremely familiar with the past animosity between Shawn Michaels and Bret Hart, less attention has been given to HBK’s dynamic with another offshoot of the Hart clan. When it came to Owen Hart, Michaels felt much more comfortable in the ring.
In his autobiography Heartbreak and Triumph, Michaels recounted that he could call matches on the fly and “mix things up” with Owen. Unsurprisingly, some of Owen’s best matches in the WWE—such as his bout at In Your House: Rage in the Cage and his tag team title defense with British Bulldog in the May 26, 1997 episode of Raw—involve the Showstopper.
9 STRUGGLED WITH: Mr. Perfect
Michaels' Matches With Hennig Were, Well, Imperfect
To be clear, Michaels didn't have a hostile relationship with Curt Hennig. The two men were peers in the AWA and WWE, and Michaels looked up to Hennig as a charismatic performer with a raucous sense of humor. However, when their paths crossed inside the squared circle, something just didn't click.
In Heartbreak and Triumph, Michaels chalks this up to the fact that both men thrive on selling their opponents' offense. Because of their identical in-ring approaches, they struggled to find the next gear when they worked with each other. This was evident at SummerSlam 1993, when their highly anticipated showdown turned out to be an 11-minute disappointment.
8 LOVED WORKING WITH: Mick Foley
Mankind Brought Out HBK's Vicious Side
Late into Shawn Michaels' first reign as WWE Champion, he had a title defense against Mankind at In Your House: Mind Games. Though Michaels and Mankind wasn't the most exciting matchup on paper, what followed was an intense match that lived up to the standards of both men.
RELATED: 10 Best Matches Of Shawn Michaels' WWE Career (That Weren't At WrestleMania)
Despite the finish being muddied by interference from Vader, the action in this 1996 PPV match was undeniably gritty. Michaels and Foley loved this encounter so much that they gave high praise for it in their respective autobiographies. Said HBK of the Mickster: "Mick was very pleasant to work with and very good."
7 STRUGGLED WITH: Shane Douglas
Hard To Enjoy Wrestling When You Don't Get Along With Your Opponent
For one reason or another, Shawn Michaels and Shane Douglas in the ring was like oil and water. From Michaels' point of view, Douglas was more hype than substance once the bell rang.
"He was a dirtsheet hero," Michaels wrote about Douglas in Heartbreak and Triumph. "They built him like he was the second coming, but he had little talent." It's safe to say, then, that HBK has little reason to reminisce about his in-ring encounters with the Dean Douglas character.
6 LOVED WORKING WITH: Undertaker
The HBK Vs. 'Taker Rivalry Has Produced Several Classic Performances
Michaels' deep-seated respect for Undertaker dates back to the '90s, a time when both men were helping the company transition from the Golden Era into the New Generation. On many occasions, Michaels has heaped tons of praise on 'Taker, commending his fellow Texan for his cool demeanor and unparalleled in-ring savvy.
HBK and The Dead Man are both wrestling artists of the highest order, and their matches at WrestleMania 25 and WrestleMania 26 are undoubtedly their magnum opus. The stakes in these high-profile clashes—Undertaker's streak, Michaels' wrestling career—were done justice thanks to the storytelling excellence of both Hall of Famers.
5 STRUGGLED WITH: Vader
Michaels Was Infuriated During Their Big Title Match
Throughout his Hall of Fame career, Vader was an impressive physical specimen who held his own against the biggest names in the wrestling industry. If you asked Shawn Michaels, though, he’d probably tell you that this wasn’t exactly the case during their SummerSlam 1996 title match.
During that match, Vader messed up a spot in which Michaels was going to attempt a top rope elbow drop, land on his feet as the big man attempts to roll away, and drop an elbow anyways. Michaels, whose mercurial personality as an in-ring perfectionist was in top form, proceeded to kick Vader and yell “Move!” to vent out his frustration.
4 LOVED WORKING WITH: Triple H
Quite Simply, These Two Men Clicked
There's a different pep in your step when you're working with your best friend, and in the case of Shawn Michaels and Triple H, their closeness translated into one of the best rivalries of the Ruthless Aggression era. Fuelled by a brotherly relationship that goes back to 1995, HBK and The Game wrote many dramatic chapters of an intense rivalry that raged for years.
RELATED: 5 Ways Triple H & Shawn Michaels Are Similar (& 5 Ways They're Different)Before they made life miserable for the McMahons in their 2006 DX reunion, Shawn and Hunter fought tooth and nail in title matches and non-title matches alike. Their body of work includes a Non-sanctioned Match at SummerSlam 2002, a nail-biting World Heavyweight Title match on Raw in December 2003, and a Hell in a Cell match in June 2004.
3 STRUGGLED WITH: Sid Justice
At Royal Rumble 1997, The Hometown Hero Had A Rough Time
In the '90s, Michaels loved working alongside and against a giant of a man, whom HBK considered to be a creative mind and smooth operator. That giant of a man, however, was most certainly not named Sid Justice.
Case in point: Michaels thought that this WWE Title match at Royal Rumble 1997—held in his hometown of San Antonio, Texas—was lackluster. He attributed this disappointment to two reasons: dealing with the flu that day and having to carry Sid in the main event. If Michaels' good buddy Kevin Nash had been around at that time, they might have had a better showing. Instead, Michaels' lack of chemistry with Sid preempted any hopes of a high-quality main event.
2 LOVED WORKING WITH: Chris Jericho
Their Feud Was The Wrestling Gift That Kept On Giving
The WrestleMania XIX match between Shawn Michaels and Chris Jericho was special to both men for different reasons. On one hand, Michaels found a perfect dance partner who could help him achieve an incredible WrestleMania comeback. On the other hand, Jericho got to tangle with his childhood hero—a man whose in-ring style he emulated—on the Grandest Stage of Them All.
If this had been the only major program between these two, Michaels and Jericho would still be brimming with fond memories of in-ring competition. Fortunately for wrestling fans, these two would engage in a passionately fought series of matches in 2008. These stellar encounters illustrate the creative satisfaction shared by HBK and Y2J whenever they were paired with each other.
1 STRUGGLED WITH: Goldberg
Did HBK Say "Who's Next" Any Time He Was Pitted Against Big Bill?
There's a school of thought among HBK fans that his second major WWE stint, which began in 2002, was even better than his first. Be that as it may, Michaels still came across dance partners that were very difficult to tango with. One of these performers was WCW icon Bill Goldberg.
In Heartbreak and Triumph, Michaels named Goldberg and Sid as two of the most difficult opponents that he's ever had to work with. According to Michaels, Goldberg—like Sid—is tough to move around and highly physical, almost to the point of being dangerous. This, perhaps, is why there's no Shawn Michaels vs. Bill Goldberg match included in the catalog of all-time HBK classics.
