The legendary career of Shawn Michaels featured classic matches and incredible storylines associated with the good times. Michaels was viewed as a generational performer who performed at a level only a handful of wrestlers could ever match. The memorable angles like forming D-Generation X, feuding with Bret Hart or becoming obsessed with The Undertaker’s WrestleMania streak showed his best storylines.

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However, there were also angles that should have worked on paper to miss the mark. Michaels was rarely putting out poor performances, but that didn’t mean he always could escape bad ideas. WWE placed him in a few angles that just couldn’t work out. The following storylines for Michaels failed even though many thought they would work.

8 Becoming WWE Commissioner

The retirement of Shawn Michaels in 1998 saw WWE trying to find other ways to bring him back to television. Michaels returned in the authority figure role as the Commissioner of WWE replacing Sgt. Slaughter.

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WWE ran a storyline of Michaels betraying his former friends of D-Generation X to help Vince McMahon and The Corporation. Michaels didn’t come off as effective as others in the role and fans had no idea how to react to him. WWE missed out on finding an ideal position for Michaels during his time unable to wrestle.

7 Love Triangle With Sherri Martel & Rick Martel

The heel turn of Shawn Michaels to become a singles star featured various changes to his character after ending The Rockers. Sherri Martel became the manager of Michaels during his singles run as one of the better heels.

Another heel character Rick Martel entered the picture for a rare love triangle with three villains. The idea seemed fun at the time, but they never had a good payoff due to their big match ending in DQ. Fans not knowing who to root for ruined the chances of success for the storyline.

6 Pam Anderson Picking Diesel Over Him

WWE getting Pam Anderson to appear at the Royal Rumble 1995 and WrestleMania 11 events was a huge move. The Baywatch actress was one of the most popular actresses when advertised to accompany the Rumble winner at WrestleMania.

An interesting little part of the storyline featured Anderson opting to walk WWE Champion Diesel to the ring instead of the Rumble winner Michaels. The idea made sense due to the character alignment, but the major name didn’t create much excitement compared to other big celebrities who appeared at WrestleMania.

5 Tag Team With Steve Austin

The infamous retirement of Shawn Michaels “losing his smile” and vacating the WWE Championship in 1997 led to him returning that same year. Michaels entered a storyline as the unlikely makeshift WWE Tag Team Champions with Steve Austin.

WWE had Austin and Michaels win the belts from Davey Boy Smith and Owen Hart as enemies of the Hart Foundation. The unexpected team ran into trouble by having a singles match as the tag champs. Fans were more focused on their respective battles with Bret Hart and others to make this promising angle become a secondary part of the bigger picture.

4 Past Vs Present Feud With Chris Masters

WWE decided to have Shawn Michaels try to elevate a younger star when his short-term heel run feuding with Hulk Hogan ended. Michaels went back to the face role one night later and instantly entered a feud with Chris Masters.

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The Unforgiven 2005 match featured Masters trying to prove he was the future of WWE by facing arguably the biggest legend in a singles match. This program has worked many times in the past, but Masters just couldn’t look like an equal to Michaels throughout the feud and match.

3 Feuding With Ken Shamrock

The first year and a half of Ken Shamrock’s WWE career became underrated since he didn’t ever win the WWE Championship. Shamrock did have the fan support to challenge for the title at one point against Shawn Michaels.

The Montreal Screwjob saw Michaels needing a new opponent after winning the belt since The Undertaker and Steve Austin were challengers for the following year. Shamrock could have been a viable threat to Michaels, but WWE ran a DQ finish for the match. The rematch never came and Owen Hart attacking Michaels was a bigger deal than Shamrock’s sole PPV title shot.

2 Joining New World Order

WWE brought Shawn Michaels back in 2002 after his retirement away from the ring. Michaels had cleaned his life up and was planning to make an in-ring return that summer. The return of Michaels came in shocking fashion as a member of WWE's New World Order.

Hulk Hogan and Scott Hall leaving the group led to Kevin Nash leading the new core of X-Pac, Big Show and Booker T. Michaels kicked out Booker and seemed ready to co-lead with Nash. However, the faction ended abruptly when Nash tore his quads and Michaels never got to have his in-ring return until afterwards.

1 Comeback Match With Triple H Vs Brothers Of Destruction

The worst idea of Shawn Michaels’ career that looked good on paper featured his one-match return in 2018. Michaels was adamant about not breaking his epic 2010 retirement until WWE came calling with a massive payday for one of the Saudi Arabia shows.

The idea was to have Michaels reunite D-Generation X with Triple H against The Undertaker and Kane. WWE received huge paydays to have legend attraction matches and Michaels felt the storyline could work.

Undertaker talking Michaels into having another made sense as the person responsible for his retirement, but the match was a disaster. All four wrestlers had a rough night with sloppy action and sad botches leading to embarrassment.