Shawn Michaels is regarded as one of the greatest professional wrestlers of all time, delivering world class matches across the span of decades.

From the Rockers to retiring at Wrestlemania, Shawn Michaels has done it all in the WWE and leaves a legendary legacy behind him. The two decades of the Heartbreak Kid are very different, a brash and outrageous heel versus the season veteran that fans laud and respect. We take a look back at his career and decide which era was better: The 90s or the 00s.

90s Shawn Michaels

When you think of the HBK’s run in the 90s, the first thing that comes to mind is the formation of D-Generation X and the legendary segments between Michaels, Triple H and Chyna.

From Michaels and the Game wearing protective masks to talk to Sgt. Slaughter, to Mike Tyson joining DX, the group created hilarious moments that are a huge part of WWE history.

But the Showstoppers most important run came during the New Generation, helping to carry the company during an incredibly difficult time alongside Bret Hart.

During this time, Shawn Michaels won three Intercontinental Championships and two WWF Championships as well as providing some legendary moments. Him superkicking Marty Jannetty through the barber shop window and winning back-to-back Royal Rumbles are just two of many.

HBK was vital for the WWF at the time, helping to innovate a number of classic matches that are still used by the company to this day.

He had the first ladder and Iron Man match with Bret Hart, and the first Cell match Undertaker.

This Iron Man match was one of the Showstoppers crowning moments, winning 1-0 in sudden death overtime of the hour-long match as “the boyhood dream came true.

Despite all of this, you cannot discuss HBK in the 90s without discussing the dark side of him. He influenced the unjust firing of long-time friend Marty Jannetty, buried Vader backstage to Vince McMahon, and of course the Montreal Screwjob.

Michaels played a huge part in the infamous Screwjob, regardless of whose account of events you believe, and was the pinacol of his backstage politicking.

HBK ended his run in the 90s at Wrestlemania 14, putting over Stone Cold Steve Austin and helping to put the Attitude Era into full motion with the Texas Rattlesnake at the top.

2000s Shawn Michaels

After a four-year hiatus from the ring, Michaels returned with a bang, clashing with Triple H in an exceptional street fight at Summerslam 2002.

HBK’s next match was yet another classic, as he won the World Heavyweight Championship in the first ever Elimination Chamber match. This showed that Michaels still had the trust from the company to debut new match types.

Michaels showed in his return that he hadn’t missed a step in the ring, but he seemed to develop the story telling element of his matches. He became of the best storytellers in professional wrestling and made his matches, particularly at the biggest show of the year, must see matches.

HBK established his role as Mr. Wrestlemania upon his return, putting a some of the best matches in the events history. First, he took the opportunity to pass the torch as he helped establish new main event talent, including Chris Benoit, John Cena and Chris Jericho.

Michaels also gave Ric Flair the perfect end to his career, with the legendary “I’m sorry, I love you” moment giving the Nature Boy the send-off that he deserved. But the piece de resistance of HBK’s return came from his rivalry with the Undertaker. HBK and the Deadman put on one of the greatest matches in the history of Wrestlemania history as Michaels looked to end the streak.

This desperation continued as Shawn begged for another match with Undertaker at Wrestlemania the next year. The tension at that year’s Royal Rumble added so much to excellent match, with the disappointment of defeat written across the face of HBK. But when Michaels hit Taker with a super kick to cost him the world title, it was on. HBK earned himself the perfect send off, losing his career in defeat to Undertaker in yet another exceptional match, a retirement that the deadman was envious of himself.

Verdict

90s Shawn Michaels was the most valuable asset in the company at the time, taking the New Generation for his own and dragging it into the Attitude Era. But 2000s Michaels takes the win, just because of the legendary moments that he created with the retirement of Ric Flair and his matches with The Undertaker