Making his debut in 1984, Shawn Michaels has done it all. He’s been a tag team specialist and a star in singles competition. He’s been a beloved babyface and a despicable heel. He’s been a serious competitor and a goofball prankster. He’s been a top star, an old dude desperately hanging on to former glory, and an onscreen authority figure -- and not even in the order that you’d think.
And, in the process, he’s taken on some of the greatest wrestlers and biggest stars of all time. With there being so many variations of HBK over the years, it can be tough to pinpoint when he was at his best.
10 Depressing, Late Period DX
The worst version of anything in wrestling is unfortunately usually the one that includes Hornswoggle and the pre-second retirement, comedic D-Generation X involves just that. The premise is simple: Triple H throws a bone to a down-on-his-luck Shawn Michaels to get the gang back together.
This sounds fine, but unfortunately, this happened during the PG era, so none of the classic DX shenanigans were appropriate for the newly sanitized WWE. Also, Michaels was getting kind of old, so it was depressing.
9 nWo 4 Not Very Long
When Shawn Michaels joined the New World Order, it felt like fanfiction come to life for many wrestling fans. After all, he was the only member of The Kliq to never wrestle for WCW. Not even Trips can say that.
But this was the half-hearted WWE version of the nWo, and being an exclusively WWE guy during the Monday Night Wars made Michaels a weird fit for this ultimately forgettable group. At least Booker T was in WCW.
8 The Iconic Commissioner Hat
When Shawn Michaels took his first retirement from wrestling, he didn’t totally disappear from television. He ended up becoming WWE’s on-screen commissioner, a run that was most memorable for his cowboy hat, which is much more stylish than his later straw numbers.
His stint as Commissioner could have been interesting, as he could be pitted against his former buds in DX, but it never really reached the potential it could have. As a result, it was ultimately forgettable.
7 Old Man Michaels
The “Hall of Famer” era of Shawn Michaels is a weird one. WWE would cart him out for various nostalgic ratings grabs, and he’d seem more like a kooky Texan uncle than the egocentric male stripper he’s best remembered as.
WWE Legend Shawn Michaels is a bit of a mixed bag because it includes the much-reviled Saudi Arabia match where everybody got injured, but then there’s Michaels as the lovable co-parent of NXT who doesn’t know how to wear face masks and talk at the same time.
6 Shawn the Degenerate
D-Generation X is maybe the perfect balance of the serious and silly Shawn Michaels. As a co-founder of DX, Michaels was a crude and rude heel but his extremely Attitude Era antics alongside Triple H and company eventually won fans over -- and is a lot more fun than the late period DX stuff.
Moreover, this era of Shawn Michaels includes that great WrestleMania moment with Stone Cold Steve Austin and Mike Tyson -- just a heartbeat before Michaels’ first retirement.
5 The Boy Toy
Fresh off of Superkicking tag team partner Marty Janetty and throwing him through a window, Shawn Michaels embarked on his first singles run as a heel nicknamed “The Boy Toy.”
With Sensational Sherri as his manager/entrance music singer and an obsession with staring at himself in mirrors, this era would include Michaels’ first singles title win, the Intercontinental Championship. However, this brief period would be a prelude to Michaels’ best heel run.
4 Babyface Champion
In 1995, Shawn Michaels would disappear for a spell and return as a babyface, winning his first world titles in the process in the classic Iron Man match at WrestleMania XII, and becoming one of the top stars of the New Generation era.
However, for many fans, this period of Shawn Michaels would be marred by controversy thanks to all the juicy tidbits of backstage drama and Kliq politicking that would result in moments like the Shane Douglas burial and the infamous Montreal Screwjob.
3 The Rocker
As much as Shawn Michaels was an incredible singles wrestler, his tag team years alongside Marty Jannetty as The Rockers (a.k.a. The Midnight Rockers) shouldn’t be forgotten.
Sensations in the American Wrestling Association and a strong midcard act in the late ‘80s/early ‘90s WWF, The Rockers were an attempt to cash in on the success of The Rock ‘n’ Roll Express, but ended up becoming a beloved act themselves thanks to their high-flying, pure babyface shtick.
2 Back From Retirement
There aren’t very many wrestlers who retire for nearly half a decade and then come back even better than they were before, by many fans' standards. But Shawn Michaels made a glorious return in 2002, kicking off an incredible second wind for a star that many fans had written off as long gone.
It was during this period where Michaels put on classics with The Undertaker, Ric Flair, and had a great feud with Chris Jericho.
1 The Heartbreak Kid
“The Boy Toy” was a great start for Shawn Michaels, but he really hit his stride when he became The Heartbreak Kid. It was at this point where he got Diesel as his bodyguard and started really making an impact as a heel.
The big highlight of this run is Michaels’ incredible WrestleMania X ladder match with Razor Ramon -- the second ever in WWE history and a classic match in its own right. It was this run that would establish Michaels as a major star in the company, leading to future accolades.