Say what you want about Shawn Michaels. The man knows how to get people talking. From air fucking the Canadian flag to kicking the holy bejeezus out of Marty Jannetty to the point he's still talking in 1980s jive to this day (I kid, kind of), he's had a ridiculous run as a hell during his WWF/E career. So, for starters, let's talk The Superkick Heard Around the World, V1.
I don't think I need to go into detail about what made this moment happen, but I'll give you the Cliff's Notes because reasons. And we're talking mostly kayfabe because fuck all the behind the scenes insanity; we'd be here all damn day. The Rockers were a tag team consisting of Michaels and the aforementioned Jannetty. In late 1991, early 1992, there were signs of dissension in the duo. This was seen in incidents such as Jannetty rolling Shawn into the ring to get pinned versus Ric Flair (Marty was thought to have really been helping, but angry Shawn took it as a slight) and a loss against the Legion of Doom. Classic tag team break-up shit, right?
And then this happened.
Straight from there, possibly thanks to both Marty bleeding from the attack and Marty then being suspended by WWF, we got the Heartbreak Kid come out of nowhere. Gone was the rando-midcarder appeal that'd kept people tuned into Michaels' matches. That was replaced by a cocky, "Sexy Boy" swagger that wouldn't have looked too off if Gorgeous George pulled the same stuff back in the day. He also had, for whatever reason, Sherri Martel as his manager. After some crazy matches, including the WWF's first ladder match versus Bret Hart, Michaels won the Intercontinental Championship.
After Michaels' return from a suspension in early 1994, we got Razor versus Michaels. Do we really need to talk about this match? It's fucking classic. Go look it up if you've never seen it. It also solidified Michaels as a legend in some ways, especially since Razor versus Michaels at WM X was one of the few WWF/E matches to get a five-star rating from Dave Meltzer. The build-up for the match was solid and the in-ring action was legendary. It also helped further Michaels' heel persona.
During 1993 and 1994, we were also treated to "Two Dudes with Attitudes," the tag team of Michaels and Diesel (see a pattern here?). An integral part of Michaels' heelish ways, bodyguard Diesel helped Shawn lie, cheat, and super kick his way to the Intercontinental Championship in mid-1993 (versus, who else, Marty Jannetty) and a tag team title reign. In mid-to-late 1994, Michaels' heelish ways got the best of him, as he ended up inadvertently hitting Diesel with Sweet Chin Music, breaking up the group. Again, see a pattern here?
After getting his ass beat by Sycho Sid post-WM XI, Shawn turned face, Shawn won his third IC Championship, we got the Curtain Call, and so on. It's not that those moments were uneventful; they're just more face than heel. With that said, we're kind of glossing over them. But, as much as I want to keep things most kayfabe-related, life has a funny way of imitating art...and vice versa.
After losing his smile, then returning months later, Shawn Michaels and Bret Hart's rivalry hit a fever pitch. While still a face to Hart's heel, we got the "Sunny Days" comment and Shawn hitting The Undertaker with a steel chair while aiming for Bret at SummerSlam 1997. This personal and on-screen feud between Michaels and Hart led to England trying their hardest to pelt HBK with garbage, the first HIAC match (classic), the infamous Montreal Screwjob (classic albeit overdiscussed at this point) and the first iteration of D-Generation X.
The first DX was...interesting. I don't mean that in a bad way, though. They were pretty much the nWo with a lot more asshole thrown in for good measure. And when I say "a lot," I mean "a lot." While, technically, heels out the ass, their "we don't give a fuck" attitude quickly won over fans. Sure, we had to deal with DX doing black face (seriously, Triple H, what the fuck?), but the group was monumental in its heelish insanity. They even got Mike Tyson to punch out Shawn Michaels. However, through this original iteration of DX (and Michaels' first retirement), we also got heel Commissioner HBK who eventually became part of The Corporation.
Yes, little Jimmy Mark, it was like The Authority, but exponentially better. Now, fuck off. Grown folks are talking.
In 2002, HBK joined the "new" nWo. Uh...it's the nWo in WWE. It's just as weird as you thought it'd be. After getting Pedigreed by Triple H on Raw close to SummerSlam 2002, Michaels became a fan favorite again, putting on some pretty classic matches. Just as with his 1996 return, we're not talking about face Shawn Michaels. So, with that said, it'd be three years before we got the heel HBK and when he returned? Fucking hell, was it beautiful?
No, seriously. Go look up the HBK/Hogan match at SummerSlam 2005. It's trollololol central. Sure, you can say that Michaels was being immature. But when I watched this match? All I can think about is how amazing it was to see Michaels oversell the hell out of everything given to him as the ultimate "fuck you" to Hogan.
After this match, you could argue that Michaels was a face for the rest of his career as an active wrestler. Yes, that's including his hour-long match with Cena (one of my favorite Cena matches), him "retiring" Ric Flair, and his match at WMXXV. I'd prefer not to discuss his involvement in the Daniel Bryan vs. The Authority storyline because we all knew that he'd side with Triple H, regardless of his training DB or whatever. But, all in all, Shawn Michaels' heel work surpasses many. He let his competitive streak (and more) seep into his storylines even more than some and, because of this, he was able to straight up be an on-screen asshole. And we fucking loved him for it.
-Speed
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