The Undertaker seems at peace with the way his career wrapped up after battling with this for about 10 years. He deserved this satisfaction after such a legendary career in which he endured so many injuries to entertain the WWE universe. The Undertaker is without a doubt the greatest character in WWE history. In theory he could have retired 15 years ago – he was so respected that no one would have complained. However, he is such a legendary figure in WWE that he of all people deserved to retire in a headspace where he was very satiated with the way his career ended.
Ironically, this also happened exactly a decade after The Undertaker wrestled Shawn Michaels at WrestleMania 26 and retired him. The reason this is so ironic is because The Undertaker was searching – for a decade – for the same level of clarity when it came to his career that Shawn Michaels had with the way his career ended. After a decade Mark Calaway has reached a peaceful state of mind and is comfortable hanging up the boots – that is indeed a satisfying state to hold after an extremely successful 30-year career.
This seems like a fitting time to chronicle The Phenom’s career after he has achieved peace and clarity (ironically enough he finally got the clarity he was looking for when he stopped looking so hard for it.)
Calaway first began his career in 1987 at the Dallas Sportatorium working for WCW and was originally managed by the man who would eventually become Paul Bearer in WWE. These two men developed a working relationship very early. His time in WCW was crucial because that is where Ole Anderson told him in 1990 that no one would ever legitimately pay their hard-earned money to see him perform. This was a crucial turning point for Calaway. When he received this advice, he had two options – 1) react by doubling down on whatever his current gimmick was, or 2) respond by listening and taking in the criticism – analyzing it to see what parts of it are true if any and using it for self-reflection.
He obviously decided to go with the second option, and subsequently became a legend by committing to his character more than anyone has ever done. He listened to the criticism he received and used it to fuel his passion – similar to what Lamar Jackson is currently doing in the NFL.
Calawy made his WWE debut at Survivor Series 1990 and defeated mostly jobbers until his first rivalry that meant anything – defeating Jimmy “Supefly” Snuka at WrestleMania 7 in 1991, following that with a WWE championship victory over Hulk Hogan later that same year.
The Undertaker’s most difficult opponent was arguably Giant Gonzales in 1993 because Gonzalez was so physically limited it was a guessing game every night to figure out how much or how little Gonzalez could do. The Undertaker has openly said that working with that particular opponent probably took years off his career (it still lasted a very long time, so I have no complaints about that).
The Undertaker did not win the WWE championship again until WrestleMania 13 when he defeated Sycho Sid. Taker’s most memorable feuds between 1991 – 1997 were probably with Mankind in 1996 – with the Boiler Room Brawl at SummerSlam 1996, the Buried Alive match at in Your House 11: Buried Alive, in the match at Survivor Series 1996 with Paul Bearer suspended above the ring in a steel cage.
As WWE champion in 1997, The Undertaker subsequently entered an elaborate storyline surrounding his half-brother Kane (who Taker thought was his biological brother for their entire lives). As it turns out, The Undertaker’s mother had an affair with Paul Bearer and Kane was born. This is all in storyline of course, but this takes a lot of creativity to make this storyline work.
After Shawn Michaels cost Taker the WWE championship at SummerSlam 1997, The Deadman challenged Michaels to the first-ever Hell in a Cell match at Badd Blood: In Your House. Michaels’ primary job in this match was to sell and make The Undertaker look dominant. The Undertaker needed to tell the bulk of his story with Kane with facial expressions – because Kane finally made his debut with WWE which universe had anticipated for months.
The Undertaker refused to fight his brother for about six months until the story culminated with a match at WresttleMania 14 between he and Kane. Undertaker got the victory in an excellent match, and subsequently lit his brother’s arm on fire about a month later in the first Inferno Match in WWE history. Also, I would be remiss not to mention the Hell in a Cell match with Mankind in 1998.
Undertaker was slightly inhibited physically after his first hip replacement in 1999 – which coincided with his Ministry of Darkness gimmick.
Undertaker adapted his character to the times in 2000 in which wrestling characters were trending more towards being based more on the real personalities of the performers. Calaway introduced The American Bad Ass, which is essentially his real-life personality with the volume turned up.
Taker would then to pivot his character and become Big Evil for the next couple years. He won a WWE championship and even challenged – and defeated – Ric Flair at ‘Mania in 2002.
The Undertaker made his return to WWE at WrestleMania 20 in March 2004 as the Deadman in a match against Kane after The Big Red Machine buried the Big Evil persona of The Undertaker alive at Survivor Series 2003 (Undertaker defeated Kane at ‘Mania 20 as part of the streak. After this victory the streak expanded to 12 – 0, becoming more and more legendary each year).
Undertaker would then get into his groove as a performer – by defeating the likes of Randy Orton, Mark Henry, Batista at Wrestlemania 23 and Edge at WrestleMania 24 (both for the World Heavyweight Championship). However, his greatest accomplishments might have come in 2009 – 12 at WrestleMania when he faced Shawn Michaels two years in a row (including retiring HBK in 2010), immediately followed by two consecutive years of excellent matches with Triple H (I attended WrestleMania XXVIII myself in Miami, Florida).
Undertaker’s most underrated (or at least one of the most underrated) ‘Mania matches was in MetLife Stadium in 2013 against CM Punk. In all likelihood it’s probably because there is a stigma surrounding Punk to a certain degree. He and Vince McMahon ended their relationship in 2014 on unsteady terms – and the two sides have had difficulties finding common ground ever since. Nonetheless, in that match Undertaker extended his undefeated streak at ‘Mania to 21 – 0.
Who can forget the night Brock Lesnar ended the streak at WrestleMania XXX? This was by far the most meaningful accomplishment Lesnar has ever had in WWE, and it was extremely unselfish of The Undertaker to put The Beast over to ensure the longevity of the business. Not to mention that Taker proved his toughness (as if he hadn’t already) by wrestling a good chunk of the match with a severe concussion. He detailed in the WWE Network documentary that aired recently that he does not remember any of the match. Taker completely lost his confidence in the ability of his body after this and spent the next few years trying to get it back. The low point for him came in 2017 at WrestleMania 33 against Roman Reigns, who was a young stud at the time.
Fortunately, The Undertaker had surgery for some nagging injuries and felt much better. The Deadman had a fantastic match with John Cena at WrestleMania 34 in 2018, but he (and probably the entire WWE universe) would have liked for The Undertaker to have been tested a little more to see if he was still capable of putting on a 30-minute classic match.
The Undertaker was legitimately okay with the idea of not being on the WrestleMania 35 card in 2019 until the show actually started and he got the feeling in the pit of his stomach telling him that he should be out there. Unfortunately, Undertaker had to live with this misstep. Taker had his next match at Extreme Rules in July 2019 in a tag team match. This was a great night because the match exceeded Mark Calaway’s expectations. Actually, a month before that in Saudi Arabia, a bad day at the office happened for Taker and Goldberg, but the most important part is how satisfied Taker was after the Extreme Rules tag match.
Undertaker was then approached by AJ Styles about working a ‘Mania match in 2020. Taker agreed because he saw AJ in the same light as Shawn Michaels. As a result of the pandemic stuff, the two men did not get the opportunity to deliver a classic wrestling match that they both envisioned. The Boneyard match, which was shot like a movie, worked out about as well as it could have. Most importantly, The Undertaker was satisfied with the way the match was put together. To summarize: Mark Calaway can now retire with mental clarity.