
My Ric Flair standom makes this hard for me to say, but I think I have to: Shawn Michaels may be the greatest in-ring performer of all time. He didn’t have the interview skills or longevity of Ric, but you can put his matches next to Flair’s and make a valid comparison. Also, unlike Nature Boy’s career, I was able to watch Shawn’s WWE run from the beginning to the end. He started at WWE right when I started watching in the late 80’s.
At Wrestlemania XXVI, Shawn Michaels lost a Career vs. Streak (as in The Undertaker’s 17-0 Wrestlemania streak, not “loser has to streak”) match and had to retire. I was fully convinced that Michaels was going to win, so the ending and realization that it was all over came out of nowhere.
After drinking my sorrows away and reliving childhood through HBK, I decided to share my most memorable Shawn Michaels…umm…memories with the rest of you.
1992 – “The Kick”
I was like four when this happened and it changed my life. Shawn Michaels came to the WWF as a member of The Rockers with Marty Jannetty. They were my favorite tag team and seemingly inseparable until one Saturday with Brutus Beefcake (yes, that was his real name) when Shawn turned on Marty, kicking him in the face and throwing him through the barbershop window. For the kiddie era of the ’90s, this was a particularly dark angle that instantly made Shawn one of the most hated wrestlers in the business.
1994 – “The Ladder”
Ric Flair has said in a few interviews that Shawn Michaels had a match with a ladder- there just happened to be another man in the ring. This match changed the face of wrestling, making revolutionizing the art of high-flying while introducing a new match that has become a staple in wrestling. There had been ladder matches before, but they all sucked until this one that landed HBK as a top star in the company.
1995 – “The Rumble”
The Royal Rumble. 30 men enter the ring. One man survives. Michaels was the first man in and lasted an hour to win. It was the first time anyone had accomplished that feat and the beginning of his push to the world title.
1996 – “The Iron Man”
Shawn Michaels and Bret Hart were the two top stars of the mid-90s in the WWE. They were also the best wrestlers. So it was like a wrestling dream to see them have a one-hour match at Wrestlemania. Though the match dragged a bit, it was still amazing that they could wrestle for that long and tell a great story. It the end, Michaels won his first championship, beginning the HBK era of the WWE.
1997 – “The Smile”
Shawn Michaels and Bret Hart legitimately hated each other behind the scenes, culminating in a real backstage fistfight. Shawn was scheduled to drop the title belt to Bret at Wrestlemania XIII, but he suddenly got out of it by finding out he had a “career-threatening” knee injury. He forfeited the belt and never had to lose it to Bret, in a move that people still think was a cover-up for not wanting to lose to the Hitman. When Shawn dropped the belt, he gave he most suspect speech in wrestling history, crying and saying he “lost his smile.”
1997 – “The Group”
The WWE was getting beat in the ratings by the crappier WCW, so they had to change the playing field. Kiddie gimmicks were replaced by crotch grabs and “suck it” chants. Shawn Michaels, HHH and Chyna led the charge by forming Degeneration X. The USA network crapped its britches every Monday because it had no clue what DX was going to do on a weekly basis. To poke fun at the censors freaking out, DX put together this hilarious skit. When I point at my sack, I get what the kids call “restraining orders” so it’s nice to see people get paid to do it.
1997 – “The Cell”
The ladder match wasn’t Shawn’s only innovative match. During his first feud with The Undertaker, HBK and Taker wrestled in a cage that, for the first time in WWF history, had a top on it. Of course, Michaels had the idea to fall off of the top. Basically, he got his ass kicked for 30 minutes in an amazingly bloody match.
1997 – “The Screwjob”
Shawn enacted the best revenge on Bret Hart but taking part in the most controversial match in wrestling history. Bret was about to move to WCW. He was the champion and his last match was againt HBK in Bret’s hometown. He clearly didn’t want to drop the belt to Shawn, so Vince McMahon had the referee ring the bell when Michaels put Bret in the Sharpshooter. Though Bret didn’t submit, the belt was awarded to Michaels who pretended like he had no clue what was going on though he was in on it the whole time. It was the most devious display of when real life imitates a wrestling storyline.
2002 – “The Return”
Get this: Shawn broke his back in a match with The Undertaker in 1998 that kept him out of wrestling for four years. His first match back with HHH was supposed to be a rugged street fight blood bath. Instead, Shawn put on a 45-minute showcase that defied logic.
The crowd watched the match legitimately worried that his surgically repaired back would get hurt again. I was jumping up and down watching this match at home. Shawn took the time to find God and get over his drug addiction, probably a big part of the reason he is still able to wrestle well into his 40s at such a high level.
2008 – “The Retirement”
Shawn Michaels ended Ric Flair’s career at Wrestlemania XXIV. I don’t want to talk about it. Next.
2009 – “The Classic”
By 2009, Shawn had done it all. Ladders, cells, drugs and screwjobs. People were expecting a good match between him and the Undertaker at Wrestlemania XXV. Nobody knew that this would go down as maybe the greatest match in the event’s history. Each man took suicidal risks and the back-and-forth action made this match impossible to follow. Just ask the crowd that sat on their collective hands for the rest of the event as nothing could follow this classic.
Bonus: This isn’t by any means a legendary moment, but it was one of the most awesome endings I’ve ever seen to a match.



I came in here just to say Bret Hart > HBK, but after revisiting the clips above, it’s back to being up in the air.
One thing fasho, HBK is best Royal Rumble contestant ever.
Sweet chin music! lol. Dude was ridiculous.
@Devin Bret and HBK are two of the all time greats no doubt. I personally prefer HBK just for personality and his willingness to do crazy ass shit. Bret was pretty much perfect technically in his heyday.
Wow. Kudos to The Heartbreak Kid and also the ungodly amount of time put into this post by DD.
“The Ladder Match” is my favorite.
I’d like to see the video that shows the highlights of Shawn’s bar fighting career, and see all the parts where HHH is saving his ass from getting killed by a bunch of wasted rednecks.
Thanks for that last Shelton B superkick. never seen that one. great retrospective.
Wrestlers don’t retire. He’ll be back before the year is done and everyone will act like his L didn’t happen.
What, no Razor Ramon tribute???
I was always meh on HBK, but can’t hate because hes been great for such a long time.
Now Six-pack, 123 Kid or whatever he is, Fuck him.
Damn, this totally puts the kibosh on my Koko B. Ware tribute.
How could you forget overselling Hulk Hogan? That was easily the funniest way to make Hogan look like the joke he is; much better than no-selling.
Thanks for trivializing one of the best careers in the history of professional wrestling with your lame commentary. Get some perspective, slick.
@Levi…I got it as one of Hogan’s best matches…but def not one of Shawn’s lol…tho it was hilarious
NO ONE WHO’S IMPORTANT CARES!!! GET A LIFE PEOPLE!!!
Good Monrning!
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Haven’t watched wrestling in almost 10 years, but Shawn Michaels and Stone Cold will always be my two favorite wrestlers of all time.
Damn this took me back to the good ol’ days. I remember when the Rockers broke up like it was yesterday.
The wrestlemania 25 match was indeed a classic. The match was a hard act to follow, the matches that followed were meh compared to Undertaker vs. Shawn Micheals.
Hope to see Shawn Micheals in 5 more years maybe.
Hey asshole, stop making this a feautre on WithLeather. Nobody cares about wrestling. Its a bunch of juice monkeys PRETENDING to fight. Get a clue.
Oh shit, they’re pretending to fight? Thanks, picklestick, for pointing that out. If you hadn’t been here, we all would have kept on watching thinking that it’s totally real. You really broke down the fourth wall on that one.
Now go back to watching your favorite real shows like ER and General Hospital.