Sting and The Undertaker are professional wrestling living legends who became two of the biggest stars of their generations, and yet the two men had vastly different careers. “The Man Called Sting” worked for World Championship Wrestling throughout the 1990s and until that company was purchased by WWE back in 2001, and he also helped put Total Nonstop Action Wrestling on the map and in front of audiences who otherwise may have ignored that product. Meanwhile, Undertaker was a mainstay for World Wrestling Entertainment programming for almost three full decades. We don’t yet know, for sure, if Undertaker has wrestled his last match inside a WWE ring, but he hinted at the end of WrestleMania 33 he is ready to walk off into the sunset.
Perhaps the biggest shame of all is that we’ll probably never see Sting and Undertaker compete versus each other on the biggest show of a year. Injuries forced Sting to retire following a short stint as a member of the WWE active roster, and Undertaker may have only one match, at most, left in the tank. Who you think is better among the two may be determined by a variety of factors, such as your age, whether or not you preferred WCW or WWE shows back in the day and how much you liked over-the-top cartoon-esque wrestling gimmicks. One interesting note is that Sting and Undertaker will forever be linked together because both won title matches against the man who remains the most famous pro wrestler in the history of the North American business.
16 Sting Defeated Hulk Hogan In Title Matches
Sting’s championship victories over Hulk Hogan occurred during the dying years of WCW when those responsible for making booking decisions seemingly tossed logic away, which is why none of them are all that memorable minus what occurred in the main event of StarrCade '97.
WCW planned to recreate the “Montreal Screwjob” with Bret Hart eventually saving the day for Sting, but referee Nick Patrick failed to execute a fast count at the right time. It, thus, made no sense when the match was restarted after Hogan had earned a visible pinfall over the babyface, but Sting nevertheless stood tall for at least that one night as the WCW Champion. Looking back at moments such at this, it’s almost a wonder WCW managed to survive up through March 2001.
15 The Undertaker Defeated Hulk Hogan In Title Matches
As with Sting, Undertaker’s championship victories over Hulk Hogan came with controversial moments and interference. The “Deadman” first beat Hogan for the WWE title at the 1991 edition of Survivor Series with help from Ric Flair. 11 years later, Undertaker claimed the WWE Undisputed Championship by defeating Hogan at Judgment Day 2002 thanks to some assistance from Mr. McMahon and a steel chair.
Whatever you do, do not go back and watch the second of those two title matches, as it may be one of the worst contests either man ever had while working underneath the WWE umbrella. Regardless, both Sting and Undertaker can claim they won one-on-one Heavyweight Title matches versus Hogan. Only a handful of wrestlers who ever lived can say the same.
14 Sting Successfully Changed His Gimmick
The original Sting character who first got over in WCW was a combination of a bodybuilder and a surfer, a generic babyface with lots of energy who became a fan-favorite thanks to working with all time greats like “Nature Boy” Ric Flair. Maybe the best thing to ever happen to the wrestler was when that character was dumped in favor of Sting becoming the WCW version of “The Crow” in 1996.
This helped make Sting the top babyface in WCW’s feud with the New World Order, and the character became the persona he used in both TNA Wrestling and WWE. Give Sting credit for knowing when and how to make tweaks to that gimmick in TNA, as doing so prevented him from becoming a boring caricature of what he was when in his physical prime.
13 The Undertaker Successfully Changed His Gimmick
A popular opinion among diehard WWE fans is that Undertaker had the greatest gimmick the promotion ever created and featured. One reason for that is because Undertaker has gone through multiple changes over the decades. He debuted as a mortician who was also a zombie, and the character eventually became the Satanic cult leader of the Ministry of Darkness remembered for “sacrifices” and other controversial moments.
Following the 90s, Undertaker became a biker and the “American Bad Ass” who ditched the supernatural gimmick for several years. The “Deadman” returned at WrestleMania XX, but this version of the character was a mix of his previous gimmick combined with a legitimate fighter who had trained in mixed martial arts. These necessary tweaks kept Undertaker fresh and popular among fans even after his physical prime faded.
12 Sting Was a WCW “Grand Slam” Champion
It’s no secret Sting is one of the greatest performers in the history of the former WCW, so it shouldn’t be a surprise that he's a “Grand Slam” champion who carried every major title, at one time or another, in that organization’s history.
Sting held the United States Championship a couple of times, he was a Tag Team Champion working alongside the likes of Lex Luger, The Giant and Kevin Nash, and he held the company’s World Title a total of six times until the promotion was acquired by the WWE.
As you likely know, Sting also won numerous championships in the National Wrestling Alliance and Total Nonstop Action Wrestling, but it would not be a stretch to suggest he's largely remembered because of all that he achieved while on the WCW roster.
11 The Undertaker Never Won the Intercontinental Or United States Championships
This may not seem as much of an achievement, as the Intercontinental and United States Championships are the only two major titles not on Undertaker’s resume as of the spring of 2017. What one must realize is that Undertaker was, simply put, too big for these midcard championships, as he was pushed as a main-event wrestler very early into his WWE run.
Undertaker’s last real involvement in a feud that included the Intercontinental belt occurred all the way back in 2001, and his stint as Hardcore Champion in 2001 was meant largely to help opponents such as Jeff Hardy and Maven get over and become popular with audiences. Undertaker was a lot of things throughout his historic career, but he was rarely a mid-card act.
10 Sting’s Longevity
Those of you who only watched WWE programming or gave up on alternatives after WCW died may either not realize or have forgotten Sting first rose to a Superstar level back in the late 1980s starting with his feud with Ric Flair. We would soon learn the sky was the limit for that character, as he quickly became one of the top babyfaces in WCW history up through the middle of the 1990s and the birth of the nWo storyline.
Sting remained with WCW through that company’s final day, and he continued to perform in TNA Wrestling up through early 2014 and until he finally appeared on WWE television. For all we know, the veteran may still be performing inside of ring today had he not suffered a serious neck injury in a contest versus Seth Rollins at Night of Champions 2015.
9 The Undertaker’s Longevity
Undertaker’s pro wrestling career began in the mid-1980s outside of the WWE, meaning his active wrestling career is probably older than some of you out there reading this sentence. The majority of fans will always remember Undertaker for his 27-year run in WWE that started back in the fall of 1990. Nobody could have guessed, at the time, that such a gimmick would become a massive hit among fans to the point that he was able to take large amounts of time away from the company only to return for WrestleMania seasons each year up through April 2017.
While we don’t expect Undertaker to continue working until 2020, we would not be surprised if the WWE convinced him to have one more WrestleMania match, perhaps versus John Cena, before he officially retired nearly 28 years after he debuted in the organization.
8 Sting Was In The Last Official WCW Match Ever
Nobody out there should count any part of the awful “Invasion” angle from 2001 as being part of WCW history, as WWE purchased the rights to that company before the start of that storyline. The last official WCW television show occurred in March 2001, and the final match of that program featured Sting facing long-time rival Ric Flair.
It’s the worst match Sting and Flair ever had for a variety of reasons, but fans who grew up watching WCW will remember it because of what those two meant to the company and because of all that was to happen after Sting had his hand raised in the middle of the ring once the bell sounded a final time. The two men embraced after Sting’s victory, and a pro wrestling era ended.
7 The Undertaker Is The Greatest Big Man In Wrestling History
While discussing Undertaker for a piece published on the official WWE website, legendary commentator Jim Ross referred to the “Deadman” as “the yardstick” and “the greatest big man in the history of wrestling.” That’s high praise from anybody, let alone from such a respected individual in the industry, and it’s also hard to argue.
Undertaker was a physical phenomenon during his prime, as he could combine an assortment of power moves along with remarkable acts such as flying over the top rope and to the outside of a ring and also walking along the top rope as a gymnast journeys across a balance beam. Just as impressive, Undertaker was often willing to put his body on the line in dangerous matches that could’ve shortened his career.
6 Sting Is In Multiple Halls of Fame
Anybody out there who questions Sting’s greatness and what he meant to the pro wrestling industry need only learn about the Halls Of Fame he's in as of the spring of 2017. He was the inaugural inductee in the TNA Wrestling Hall of Fame, an honor he truly earned for everything he gave to that company. Sting finally had his night at the WWE Hall of Fame in 2016 after he waited over a decade to put pen to paper on a contract with the promotion. That same year, Sting became a member of the 2016 Wrestling Observer Hall of Fame class.
Sting wasn’t as big a star as Hulk Hogan, nor was he as good a worker as Ric Flair. The Stinger nevertheless deserves to be remembered as a legend of his time.
5 The Undertaker Will Be In Multiple Halls Of Fame
The biggest reason Undertaker is not already in the WWE Hall of Fame is because he has remained part of the company’s roster throughout the past 27 years. He never walked away, and so the promotion never had to think about bringing him back for any sort of ceremony.
At some point down the road, the WWE should probably dedicate an entire night to his induction, but such a discussion is for a different time and a different place. Undertaker became a member of the Wrestling Observer Hall of Fame all the way back in 2004, 12 years before Sting received that honor. Little did we know at that time some of Undertaker’s best WWE moments, including a list of incredible WrestleMania matches, were still to come.
4 Sting Was In Multiple Five-Star Matches
The star rating used to evaluate matches perfected by journalist Dave Meltzer is the standard borrowed, or maybe even stolen, by observers and fans to this day. It may surprise some to learn Sting was part of a pair of five-star matches (Meltzer’s highest honor outside of a pair six-star matches) back in the early 90s.
Both of those contests took place inside the War Games cell, and both featured several other competitors. In February 1991, the team of Sting, Brian Pillman, Rick Steiner and Scott Steiner lost to Ric Flair, Barry Windham, Sid Vicious and Larry Zbyszko. In May 1992, the five-man side of Sting, Ricky Steamboat, Barry Windham, Nikita Koloff and Dustin Rhodes notched a War Games win over Steve Austin, Rick Rude, Arn Anderson, Bobby Eaton and Larry Zbyszko.
3 The Undertaker’s Star-Match History
While some may argue with Meltzer’s opinion on the matter, the journalist gave only one Undertaker match a five-star rating during the wrestler’s career. That contest happens to be arguably the greatest cage match to ever occur inside a WWE ring. Undertaker battled Shawn Michaels in the company’s first ever “Hell in a Cell” match in October 1997, and that showdown remains Meltzer’s highest-rated HIAC match in history.
For those interested, three of Undertaker’s WrestleMania contests received 4.75 stars from Meltzer, although some fans out there may consider those Undertaker matches versus Shawn Michaels and Triple H as the best of his career. History will likely remember Undertaker as a better singles worker than Sting, due, in part, because of his WrestleMania resume.
2 Sting Carried The Banner For TNA Wrestling
The biggest accomplishment of Sting’s career has to be that he carried the banner for a TNA Wrestling promotion that may have died roughly a decade ago had the icon signed with WWE or walked away from the business, for good, after WCW folded.
Sting served as the big-name superstar TNA desperately needed to establish itself in front of wrestling audiences looking for an alternative to WWE shows like Raw and SmackDown, and he remained loyal to that company even when doing so made little sense to outsiders who wanted to see him make the jump to WWE. The future of what is now Impact Wrestling remains in doubt at a time when WWE is signing talent from all around the world, but that promotion likely wouldn’t exist in April 2017, at all, if not for Sting.
1 The Undertaker’s WrestleMania Record
Yes, Undertaker’s WrestleMania record of 23-2 is statistically impressive and will likely never be matched or topped by anybody who ever works for WWE down the road. No disrespect meant to Shawn Michaels, but Undertaker proved over the past two decades that he is the true real Mr. WrestleMania. His match versus Triple H at WrestleMania X-Seven helped make that one of the best ‘Mania cards in history. He and the previously mentioned Michaels produced instant classics at WrestleMania XXV and WrestleMania XXVI, and Michaels retired following that second battle.
Undertaker losing to Brock Lesnar at WrestleMania XXX will be immortalized in highlights that will air each WrestleMania season. Undertaker will always be known as the biggest star of the biggest annual event that takes place for the world’s top wrestling promotion, and that’s why we can suggest that Undertaker’s career tops that had by Sting. But then again, what do you guys think?