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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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?
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