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Sting is one of the biggest wrestling legends still alive today, who made his name in WCW. The surfer Sting character with colorful face paint and bleached blond hair was successful enough that he would be remembered as a top star based on that era alone. The Crow gimmick took him to the next level, however, as the New World Order’s top foil and one of the most distinctive figures from one of wrestling’s most successful time periods.
Sting took his time coming to WWE, and as he discussed in an appearance of Legends with JBL for the WWE Network, he wasn’t sure he trusted the company. As such, he only had about one year with WWE, and in the twilight of his career. He worked just a small handful of matches, and only two of them properly built PPV showdowns, opposite Triple H and Seth Rollins.
This begs the question what might have been had Sting signed sooner, or had the Monday Night War progressed a bit differently. This article takes a look at seven of the top legends Sting never worked in a WWE ring.
#7 Stone Cold Steve Austin
Sting worked with Stunning Steve Austin a fair bit in WCW, when Sting was the top face prior to Hulk Hogan’s arrival, and Austin was an upper mid card heel who seemed likely to mature into a main event spot. Their work in this context was nothing like what a showdown would have looked like between Crow Sting and Stone Cold Steve Austin, tip top stars from warring brands.
While both men are remembered better for their character work than their actual wrestling, they could each hold their own. In particular, Austin was a ring general who more often than not delivered in big match situations. There’s an argument to be made that we actually did see these two wrestle at their respective physical primes in the early 1990s, but seeing them clash at the peak of their popularity, during or just coming off of the Monday Night War era would have felt like a bona fide dream match.
#6 Shawn Michaels
WWE tends to reference Shawn Michaels as its all time greatest performer. It’s a debatable point, particularly as it relates to box office results. Nonetheless, he was a major star, more than capable of delivering great matches against a diverse array of opponents, and always game to excel on the microphone.
Particularly at the peak of his arrogant heel persona, Michaels could have offered a similar rival for Sting to overcome as Hollywood Hogan, with the added bonus that his athleticism, and more generally his ring chops could have helped the match deliver in the ring.
We got the briefest taste of what might have been in Michaels delivering a super kick to Sting during his match with Triple H at WrestleMania 31, but that’s hardly the same as a full-fledged featured match that might have had similar appeal and execution to HBK’s main event bout with Hogan at SummerSlam 2005.
#5 The Rock
When it comes to wrestlers who have transcended the wrestling business, no one really compares to The Rock. To be fair, Hulk Hogan and Steve Austin quite arguably have personal brands that are more immediately linked to wrestling than Dwayne Johnson does, since his acting career has taken off. Nonetheless, he’s a genuine A-list celebrity who launched his national profile with WWE.
The Rock started wrestling well after Sting, and retired from full time wrestling long before him, leaving a deceptively small window of time when this match ever could have happened—basically, just the year or so after WWE bought WCW. Sting ran out his WCW contract and then signed with TNA, missing the opportunity for what could have been a special encounter between two of the most popular wrestlers who ever lived. Sting spent most of his career as a face, and was generally agreed to be best in that role. Fortunately, Rock could play the heel or face comparably well, and as such could have been a suitable villain to oppose The Stinger.
#4 Bret Hart
Bret Hart was the standard bearer for WWE when Sting was on top of WCW in the early 1990s. It’s funny how both men’s fortunes would change in the years to follow, as they each remained main event level guys, but not without significant tumult and having to reinvent themselves to a degree to fit the changing times.
To be fair, Hart and Sting did wrestle in WCW, but the key to this article is looking at matches that didn’t happen in a WWE ring. In this case, the difference is more than a matter of semantics. In WCW, this match was never properly featured, built, or given the right amount of time in WCW, largely lost in the shuffle of The Hitman’s too frequent face and heel turns and nonsensical character path.
In WWE, we can trust these two major stars would have gotten a better story, perhaps anchored around the Scorpion Deathlock vs. the Sharpshooter as the finishing hold that each man used to iconic effect in their careers.
#3 John Cena
Sting held down the fort for WCW through the time it was a distant runner up to WWE on the national wrestling scene, through the era when it was competitive with WWE and even best WWE in the ratings more often than not, through the decline.
During none of these times was John Cena a household name. He’d only debut on the WWE main roster in 2002, over a year after the Monday Night War officially ended. It’s then when Cena might have crossed paths with Sting. Like most top talent from WCW, The Icon had opted to ride out his WCW deal before going to WWE, but unlike Ric Flair, Hulk Hogan, Goldberg, or Scott Steiner, Sting signed with Impact once his contract had paid out, and stayed there for almost a decade.
Sting-Cena would have made sense with Sting as the veteran face against the upstart heel, or potentially when Sting finally did sign with WWE, by which point both men could be called legends. In either case, the guys’ careers overlapped enough that it feels like a missed opportunity for the match to have never happened.
#2 Edge
Sting was at his best as a face, whether he was playing the clean cut, adrenaline fueled face he was in the early 1990s, or the brooding Crow character he became better known for during the Monday Night War. In either case, he was at his best when cast opposite an established champion heel who needed to be brought down a peg or two like Ric Flair or Hollywood Hogan, or against a monster heel he could slay like Big Van Vader.
Edge—particularly in the main event level conniving heel persona he took on for much of the last six years of his career—could have been a fascinating foil for Sting. Yes, this could have been an arrogant, slimy heel against a valiant hero. All the more so, Edge’s size and athleticism made him something like a younger Sting, and seeing the two clash in the late-mid-2000s could have been a lot of fun.
#1 The Undertaker
As was the case with Steve Austin, Sting actually did wrestle The Undertaker back in WCW, before The Dead Man became the legend he would ultimately be. Unlike The Icon vs. Stone Cold, however, Sting-Undertaker has taken on a life of its own as one of the ultimate dream matches fans have conjectured about for nearly two decades, that really could have happened, but never did and probably never will.
Sting and The Undertaker had comparably long, comparably high profile careers, arguably best defined by Sting being the top WCW star who never jumped to WWE, while The Undertaker was the top WWE stalwart who never jumped back to WCW. Add in their respectively dark personas when Sting was playing his Crow gimmick, and it’s a natural dream match to think about.
Had Sting come to WCW a decade or more sooner than he did, you have to imagine this match would have happened at some point, likely as not at WrestleMania. Given when Sting did arrive, he certainly could have worked The Dead Man at WrestleMania 31, but we can’t totally fault the choice to go with Triple H instead. The heel-face dynamic avoided muddying the waters for The Stinger’s only WrestleMania match, the DX-nWo interaction was a fun bit of nostalgia, and perhaps most importantly Triple H was better equipped to give Sting about as good a match as he was going to get at that point.
