Shawn Michaels' Five Best Matches Ever

With the "Heartbreak Kid" Shawn Michaels retiring from the WWE after his loss to the Undertaker at WrestleMania 26, I'm going to post what I think are the best matches in his career. His best matches were all at the biggest event of them all in the wrestling industry.

I recall as a kid living in Midwest City, Oklahoma and remembering a very young Shawn Michaels in Mid-South Wrestling in the mid-1980s. I'm fairly certain that I watched him then because my dad took my brother and I to those events all the time. He sure did come along way, and is one of the greatest single performers ever in the history of the industry. Maybe the best, and I have zero problem with anyone giving him that claim.

Anyway, here are my picks for the top five matches in HBK's career.

5. WrestleMania XIV vs "Stone Cold" Steve Austin in 1998

The Attitude Era had officially launched after the famous "Montreal Screw-job" in which Michaels was a part of and Vince McMahon becoming an egotistical boss. This turned Austin into an anti-hero of the likes no one has ever seen in the industry. Michaels was battling a hereniated disc in his back at the time, but he and Austin put on an entertaining match. The match went into the crowd and offered high impact spots throughout. Austin countered HBK's finisher into the "Stone Cold Stunner" to win the WWE Title for the first time. Michaels still put on a very watchable match despite the severe back injury that forced him into a four-year hiatus from wrestling in the ring. The Attitude Era and Austin's reign as the top star in the business changed the game after this match.

4. WrestleMania 21 vs Kurt Angle in 2005

After Angle attacked Michaels at the Royal Rumble, this match was eventually made. Angle was on Smackdown while Michaels represented Raw. This classic bout lasted over twenty minutes and it comes as no surprise as both have delivered five star performances before. This was no different as both countered each other's finishers and kicked out of them, too. Michaels leap-frogged off the ropes onto Angle, who was laid across the table during the match. After Angle kicked out of "Sweet Chin Music", he caught Michaels in his Ankle Lock finisher. Even HBK put on a believable effort in wanting to break Angle's hold, but he eventually tapped out. Great move to put these two against each other.

3. Ladder Match vs Razor Ramon at WrestleMania X

Though this match wasn't new since it had been used in other promotions, it caught the attention of diehard WWE fans that had never seen it before. Because of the performances of both HBK and Ramon, the ladder match became relevant after their match was over. Michaels performed a splash off the top of the high ladder and used it when he jumped off the top turnbuckle falling down with his weight on Ramon. Ramon superplexed Michaels off the ladder at one point in the match, too. Ramon pushed Michaels off the ladder after he used it falling on him, and HBK was tangled in the ropes as a result. Ramon grabbed both Intercontinental belts that were above the ring using the ladder to retrieve them. Scott Hall, who was Ramon, and HBK put on a clinic, and the ladder match has been commonly used more since they put on this great match.

2. WrestleMania XXV vs the Undertaker in 2009

This match has been called the best ever in WrestleMania history by those who follow the business closely. The Undertaker's undefeated streak was in jeopardy as HBK was set to end, and he came real close. Bodies flew all over the place, finishers were countered more than once, and several near fall pin attempts kept the fans in Houston on the edge of their seat the entire time. For about 30 minutes, both stole the show without any real problem, and could have easily been the last match on the card. Undertaker's "Tombstone Piledriver" had been kicked out of by Michaels in this match, but he was caught after an attempted moonsault by Undertaker. Undertaker hit his finisher again, and was able to pin Michaels after that. Undertaker's streak at WrestleMania continued to 17-0, and their rematch ended with Michaels retiring this past year. One of the best "big men" ever against the greatest performer in WM history was definitely a good idea.

1. Iron Man Match vs Bret Hart at WrestleMania XII in 1996

Most fans know the animosity that did exist between these two in and out of the ring before they put it behind them. But there's little doubt that this was not only quite possibly the best match in WrestleMania history, but of all-time. The 60-Minute Iron Match was probably expecting to have boring moments, but that was far from the case as both battled until time was up. Neither one gained an advantage by scoring any pinfalls, and the match was ordered to go into "Sudden Death" overtime with the first winning by pinfall or submission as the winner. Both guys exhausted themselves in this classic which you could clearly see with both performers. Five minutes into the overtime, HBK's boyhood dream came true when he hit his "Sweet Chin Music" finisher on Hart to pin him and win the WWE Title. Both HBK and Hart are considered to be amongst the best ever, and this match did more than prove it on this day.