Happy 49th Birthday, HBK: Shawn Michaels’ 10 Best Post-First-Retirement Matches

Shawn Michaels has one of the most unique wrestling careers ever. He went from d*ckhead drugged out political jerk who buried everyone he could while also having the best matches in the business. Then he broke his back in 1998, went on a downward spiral to nigh-overdose, found religion and came back to wrestling as a Jesus-loving nonchalant wrestler who was also having the best matches in the business.

For those of you who’ve been following my Best & Worst posts, you’ll know I’m spanks deep in matches from HBK’s “prime” in 1996. Well, here’s a shocker: I really think his matches after his first retirement hold up better more consistently than matches from his younger days. Sure, nothing will touch his ladder match or “Mind Games,” but his body of work after he came back was just all high quality. He was a much better ring technician and master of facial expressions and psychology put him in another league.

With that said, let’s celebrate HBShizzle’s (still hasn’t caught on? Damn) 49th birthday with his 10 best post-first-retirement matches.


Shawn Michaels vs. Shelton Benjamin – WWE RAW… by prowrestlingru

10. vs. Shelton Benjamin – Raw

Okay, I’m going to be honest here. The ending of this match puts it on the list. The first 80 percent of Benjamin vs. HBK is a great RAW match but the climax is a masterpiece. It’s rare to hear wrestling crowds make real life sports pops. This crowd sounded more like they saw Ray Lewis take someone’s head off than a guy do a fake thing to another guy. And it’s absolutely incredible. Benjamin was supposed to be a star after this. Then his mom happened. *pours out liquor*

9. vs. Chris Jericho Ladder Match – No Mercy 2008

Ever wish ladder matches had actual selling and a point beyond getting to the next high spot? Then this match is for you. Sure, Jericho and Michaels could have torn it up if this match happened in 1997 but this was different. This was about two guys who hated each other because a guy punched another guy’s wife and the world title just happened to be part of it. You probably won’t be yelling “holy sh*t” a bunch during this match – partly because you’re not a goober – but you’ll get pulled into what’s going on.


WWE Backlash 2007 John Cena vs Randy Orton vs… by EmilMoeller

8. vs. John Cena vs. Randy Orton vs. Edge – Backlash 2007

By 2007 we all pretty much knew Shawn Michaels was never winning a WWE title again. But dammit if this match didn’t make us believe. This match was part of the era when Backlashes were way better than the WrestleManias that came the month before. I know I mentioned the Shelton Benjamin match as ending flawlessly but this ending may have been better. We get finishing move theater that actually works out. Coming on the heels of the bleh four corners match we saw this Sunday, this match is a great watch to see how that type of match is executed perfectly.


John Cena VS Shawn Michaels WWE Monday Night… by Wrestling-Nation

7. vs. John Cena – RAW

Think about this: two of the matches on this list happened in the same week. I don’t know what possessed Michaels and Cena to have a Broadway on RAW, but they did it and it’s probably one of Cena’s best matches in his career. The pacing was perfect, Jim Ross called his ass off and bonus points for the old school “we have a match scheduled but we’ll postpone if we have to” attention to detail. This is the match that showed that John Cena can go. This match made the “you can’t wrestle” chants moot and turned Cena “go away” boos to Cena “we sort of hate you but respect what you do in the ring” boos. This is important, people.


The Undertaker vs Shawn Michaels WWE… by Wrestling-Nation

6. vs. Undertaker – WrestleMania 26

I’m going to cheat and take Brandon’s paragraph from his WrestleMania main events ranking:

I think the cool thing these days is to say that The Undertaker vs. Shawn Michaels wasn’t as good as everyone thinks, but forget that. Their match at WrestleMania XXV and the career-threatening rematch at XXVI are as good as epic, one-on-one main-event style matches in WWE get.

To the credit of the detractors, the rematch isn’t as good as the original, but it’s great, and builds and builds that weird mutual respect angle more and more until Michaels pulls himself up by Taker’s pants, slaps a 7ish-foot dead man in the face and gets GURL BYE’d with a jumping Tombstone. A JUMPING Tombstone. That shit is an exclamation point. Shawn wrestled in four decades and never learned how to throw a believable chop, but the man was an ace at selling the emotion of a story in the ring, especially when they end with him getting scooped up and tossed through the air and dropped on his head with authority.


Shawn Michaels vs Chris Jericho – Wrestlemania… by superbatista619


Shawn Michaels vs Chris Jericho – Wrestlemania… by superbatista619

5. vs. Chris Jericho – WrestleMania 19

Okay, yes, WrestleMania 17 is the holy grail but if I’m feeling troll-y I can make an argument that WrestleMania 19 was just as good. The matches were just about as good, though it missed some of the iconic moments of 17. But what I refuse to argue with anyone about is which match was the best of the night. HBK vs. Jericho put on one of the best non-stipulation WrestleMania matches of all time. The story of Jericho mimicking Michaels to surpass him was beautifully told and the execution was damn near flawless. If there’s one gripe, it’s the weak ass pin, but otherwise you won’t find many matches as good as this one anywhere. Probably in Jericho’s top five matches ever.


Shawn Michaels vs. Kurt Angle – WWE… by prowrestlingru

4. The Kurt Angle Trilogy

I’m cheating here again because this is the forgotten trilogy that should be up there with Steamboat/Flair or Punk/Joe. The WrestleMania 21 match suffered a bit from the slow pacing at the beginning. About that: I really think HBK was a bit self-conscious about his conditioning at different big matches in his career so they start off slower than he probably would like in hindsight. The Iron Man match with Bret and the match with Angle at WM 21 are examples of that. One difference: his matches with Angle were actually great. I honestly can’t pick between the ‘Mania match and the rematch with the 30-minute Iron Man match at RAW right behind them.

Anecdote: I spent a semester in Ghana and this match (along with a few other sh*tty matches) was saved on my computer so I’d watch it so I could sleep when I didn’t have electricity so I’m pretty sure I could wrestle a pillow and recreate this match but it’d look like I was wrestling in 5x gravity.


Triple H vs Shawn Michaels vs Chris Benoit… by BadDreamsComeTrue

3. vs. Chris Benoit and HHH – WrestleMania 20

So we’re not allowed to list this match anywhere according to the WWE but this was my favorite match of all time for a few years, even if you take away how happy I was to see Benoit finally get the belt. I loved everything about this match, from HBK kicking Benoit’s face off, the storytelling of HHH and HBK teaming up to get rid of the buzz saw who wouldn’t take no for an answer and the beautiful goddamn ending. It hasn’t aged as well because of the formulaic way they just alternate one-on-one scenarios instead of doing more with the triple threat scenario. Still, it’s a top main event match of all time.


WWE PPV Summerslam 2002 Triple H vs Shawn… by anthonywalker24

2. vs. HHH – Summerslam 2002

This is probably the most emotionally invested I’ve ever been into a match. This was Shawn Michaels’ first match back after back surgery and it wasn’t clear how healthy he was. I was convinced he’s poop out his spine at some point and die in the ring. Then, he masterfully set the bar low by saying they’d have a “fight” only to have a 40-minute match that would be the last good thing HHH did for a solid year and a half after. Then, I damn near cried watching Shawn look like a guy doctors told him he wouldn’t ever be again. But this was different. He was a guy who understood that at any moment his career could be over and he cherished it. Shawn Michaels’ redemption story is an inspiration no matter what you think about him, wrestling or religion. And it all played out in this masterpiece.


WWE Undertaker Vs Shawn Michaels @ Wrestlemania 25 by randy-savage1

1. vs. The Undertaker – WrestleMania 25

Did you really think anything else would go here?

I watched WrestleMania 25 on a stream (I was in a dorm at the time and couldn’t order ppvs in the building) and the stream cut off right after Undertaker hit the first tombstone. This was when the tombstone wasn’t a transitional move at WrestleMania, so I thought the match was over. I literally got up and went to get my laundry because I’d thought I’d just seen the match of the year and needed to walk it off. It wasn’t until the next morning re-watching the match that I realized I’d seen one of the best matches I’d ever see. And it just might be the best WrestleMania match ever.

It’s perfect. I honestly can’t say anything more about it.

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