The 10 Worst Things Shawn Michaels Did (In Wrestling)

Shawn Michaels is one of the most decorated and accomplished superstars in the history of professional wrestling, and we simply won't see anybody of his caliber again. The Heartbreak Kid dazzled with his incredible skill set and high-flying moves in the ring. But it was also Michaels' character and unpredictable persona that made him such a beloved legend in the wrestling world.

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Like Steve Austin, Triple H and other WWE legends before him, Michaels was the perfect guy to pull of cold, calculated and merciless moves when Vince McMahon needed it done. Here is a look at the 10 worst things Michaels did as a wrestler.

10 Impersonating Shane McMahon

D-Generation X reformed in 2006, and they engaged in a feud with the McMahon family plus the Spirit Squad. On one instance, Triple H posed as his father-in-law and mocked Vince's mannerisms, gestures and voice.

Then, Michaels appeared (using Shane McMahon's entrance theme) and copied his signature dance. The two then exchanged harsh insults towards Vince and his son, before dancing to the chairman's song "Stand Back." Michaels showed no mercy or compassion towards Shane by often over exaggerating during his impersonation.

9 Teasing Bret Hart's Return

Eight years after the infamous Montreal Screwjob incident, Shawn Michaels made a hyped up return to the city on the Aug. 15, 2005 edition of Raw. As expected, The Showstopper was met with plenty of thundering boos and angry chants from the Montreal faithful.

Suddenly, Bret Hart's entrance music began to play, and his titantron appeared on the stage. Michaels was bracing for the return of his archenemy, but fans quickly realized that this was a cruel choke by the Heartbreak Kid. There was no return from Hart that night. Michaels pulled off a mean practical joke and poured salt on the wounds by teasing the fans for buying it.

8 Tampering With Vince McMahon's Microphone

D-Generation X was banned from the arena on the July 3, 2006 episode of Raw, but it didn't stop Michaels and Triple H from wreaking more havoc on the WWE chairman. DX managed to sneak into Vince's production truck, and they were able to lock out Jonathan Coachman and WWE security.

Later on, Vince was humiliated during one of his promos, as DX tampered with his microphone by changing the voices while inserting hilarious sounds. Vince berated DX, as well as the WWE Universe, for condoning their actions. It was one of the more memorable and hilarious moments in the history of D-Generation X. Savage level: 100%.

7 Turning On Hulk Hogan

Hulk Hogan returned to the WWE in 2005, and he briefly teamed up with The Heartbreak Kid in a series of matches. That all came crashing down on the July 4, 2005 episode of Monday Night Raw, however, after the duo won a tag team bout against Kurt Angle and Carlito.

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Out of nowhere, Michaels delivered his Sweet Chin Music finisher to Hogan, thus solidifying a heel turn. This would lead to a match at SummerSlam, won by The Hulkster himself. Michaels really spoiled the mood that night when he quickly disbanded one of the greatest dream duos in WWE history.

6 Costing Daniel Bryan His Championship Match

Daniel Bryan and Randy Orton squared off in the main event of the 2013 Hell in a Cell pay-per-view, with the Heartbreak Kid acting as the special guest referee. Needless to say, fans at the American Airlines Arena in Miami were in for an unexpected surprise.

Following interference from Triple H, Michaels executed a Sweet Chin Music on Bryan, which allowed Orton to come away with an easy pinfall victory, thus becoming the new WWE Champion. Once again, The Showstopper had betrayed another beloved babyface while pulling off the jaw-dropping heel turn.

5 Impersonating Hulk Hogan

Ahead of his previously mentioned showdown against Hulk Hogan at SummerSlam, Michaels tried making a statement by impersonating his rival during a Larry King Live parody segment.

Michaels appeared with a walker and moved slowly, trying to expose Hogan as a washed up and worn down wrestler. He then proceeded to use Hogan's signature term "brother," time and time again throughout the segment - before delivering Sweet Chin Music on the Larry King impersonator. Of course, Hogan wound up getting the last laugh when he defeated Michaels at SummerSlam.

4 Disrespecting The Canadian Flag

Before he faced Bret Hart in the main event of Survivor Series 1997 in Montreal, Michaels looked to draw more heat and hatred upon himself by disrespecting the wonderful nation of Canada. He went great lengths, too. Needless to say, he succeeded in pissing off an entire country.

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Michaels brought out the Canadian flag for his entrance, and he proceeded to pick his nose with it while performing a cruel gesture with it. Of course, that led to even louder boos from the folks in Montreal. We're sure the many Canadians watching then didn't care for it, either.

3 Betraying Marty Jannetty

Shawn Michaels and Marty Jannetty were one of the most popular tag teams in the professional wrestling business throughout the '80s and early '90s. The Rockers won several Tag Team Championships together in various promotions across the United States, and it almost felt like they would never break up.

Amid belief that Jannetty and Micheals were dealing with backstage tension, the two broke up when the Heartbreak Kid attacked him during a 1992 segment of Brutus Beefcake's Barbershop. Michaels threw his long-time partner through a window, much to the dismay of wrestling fans all over. It was certainly a brutal and cold way to break up a historic tag team that captured the hearts of millions.

2 Destroying Vince McMahon's Limo

As noted earlier, D-Generation X was banned from the arena on the July 3, 2006 episode of Raw. As if tormenting Vince by tampering with his microphone wasn't bad enough, Michaels and Triple H took it another step at the end of the show.

Vince entered his limo, but once he closed the door, a series of fireworks went off inside his limo. DX then came out and mocked him for banning them that night, before wishing the WWE chairman a happy fourth of July. Michaels and Triple H just weren't afraid to cross the line when it came to humiliating their boss.

1 The Montreal Screwjob

This infamous moment of betrayal happened in both the storyline and the real-world part of professional wrestling. Contrary to what he told Bret Hart, Michaels was strongly involved in Vince McMahon's plan to double-cross the WWE icon at Survivor Series 1997.

Michaels locked in the Sharpshooter on Hart, and even though the latter never tapped out, Vince ordered referee Earl Hebner to call the match. The bell was rung, and Michaels had become the new World Heavyweight Champion. It painted an ugly picture of the WWE, especially Vince, Michaels, Hebner, Triple H and the others who were involved. Thankfully, Hart soon patched things up with all the parties - burying the hatchet with Michaels when he returned to WWE in 2010.

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