Entertainment Sports The Undertaker Knows the End Is Near, But He's Still In Search of the Perfect Match The Last Ride, a new docuseries from WWE, takes a behind-the-scenes look at the Undertaker's legacy and struggle to walk away from the ring By Jason Duaine Hahn Jason Duaine Hahn Jason Hahn is a Human Interest and Sports Reporter for PEOPLE. He's worked at PEOPLE's Los Angeles Bureau as a writer and reporter since 2017 and has interviewed the likes of Kobe Bryant, Arnold Schwarzenegger and Tom Brady. He has a B.A. in English from the University of California, Berkeley, and a Master's degree in Journalism from Columbia University. He previously worked for Complex Magazine in New York City. People Editorial Guidelines Published on May 8, 2020 01:54 PM Share Tweet Pin Email Photo: WWE Endings aren't easy, and this has been on the mind of Mark Calaway, the towering behemoth who holds an indelible place in professional wrestling history under the ring name "The Undertaker." Instantly recognizable by his wide brim hat, trademark black trench coat and iconic theme music, Undertaker has been a stalwart of the industry since Calaway debuted the menacing character at WWE's Survivor Series in November 1990. But after a storied career encompassing more than three decades of flying over ropes, crashing into tables and slamming onto mats, the 55-year-old wrestler's time in the ring is nearing its conclusion. "We're close," Calaway tells PEOPLE exclusively from his home in Texas. So, how does one of wrestling's most revered icons finally say goodbye? "When you're thinking of the old school Undertaker, that's not a character that comes down to the ring and says, 'Thank you for being with me for 30 years. It's been a great career. I want to thank...' That's not what that guy does if you're being true to the character and what people want to see," Calaway, a father of four, explains. Paul 'Triple H' Levesque Marks 25 Years as One of WWE's Most Hated — and Beloved — Villains And yet, he hasn't only thought about what a final farewell would look like — Calaway's already had some practice. In the premiere episode of Undertaker: The Last Ride, a new five-part documentary series that premieres Sunday on the WWE Network, Calaway is seen preparing for a match against Roman Reigns at 2017's WrestleMania 33. At the time, he and others believed it would be Undertaker's swan song. Though the 30-minute match was entertaining in its own right — resulting in Undertaker's second loss in 24 tries at WrestleMania — Calaway wasn't happy with his own performance (the documentary highlights one botched maneuver between him and Reigns in particular). That dissatisfaction is what ultimately drew Calaway back to the ring a year later to face fellow superstar John Cena in a bout that saw Undertaker victorious. He then returned to WrestleMania last month to face AJ Styles in a cinema-style match that took place without fans due to the coronavirus pandemic. Now, three years out from what was supposed to be a retirement match, Calaway still has his eyes set on the moment, the show-stopping performance, that will be a fitting finale for the Undertaker. Howard Finkel Who Was the WWE’s First-Ever Employee and Beloved Ring Announcer Dies at 69 "I've had this amazing career, I've been so blessed to have this career and far exceeded the expectations of when I got in this business. But I kind of want the John Elway ending, you know?" he says. "The John Elway ending, when he went out and he won a couple of Super Bowls and then retired. Or Peyton Manning, he wins the Super Bowl, then retired," he continues. "When I'm looking at it, I want that match, that match when it's just like, 'Oh yeah. Bam. I still got it. I got gas in the tank, I tore it down. Now walk away.'" The key, Calaway says, is putting on a culminating show that leaves the audience wanting more. But as The Last Ride shows, with the wear and tear he's experienced over his career, that moment is becoming more difficult to realize by the year. WWE Calaway isn't the only figure in pop culture to grapple with the finality of retirement. Michael Jordan returned to the NBA twice, and Hall of Famer Brett Favre changed his mind three times before leaving the NFL for good in 2010. Even with the pain and numerous injuries he's experienced that would cause most people to seek out retirement, Calaway says it all melts away when he walks through the curtain to the roar of a crowd. "Man, I tell you what, when those lights go out and that music starts, I don't feel anything," he says of becoming the Undertaker, a character he studied Michael Myers and Jason Voorhees to help develop before making it all his own. Why WWE Decided to Still Hold This Year's WrestleMania "On the walk to the ring, man, that's the best," Calaway continues. "You're in the zone. Nothing really hurts. And what does hurt, you don't really care because those people are showing their appreciation for you, and that's better than any drug." Calaway was a fan of professional wrestling before he ever stepped into a ring, he says, and he's remained one for the more than 30 years he's been in the business. But knowing what it is to be a fan has only made it all the more important for him to get the ending just right. WWE "I'm fighting an uphill battle and time's running out," he says. "But that's the struggle. It has nothing to do with fame, it has nothing to do with money, it has nothing to do with anything other than wanting just that, "Yeah. That's the match that I needed to go out on.'" When asked, Calaway says he isn't sure if his last match has already happened, or whether he'll be able to achieve the one he envisions. But, just as life in the squared circle has taught him, he is prepared for whatever happens next. "In wrestling sometimes you're on top, sometimes you're on the bottom, and life is the same way," Calaway explains. "You have to persevere and you have to ride it out." "Nothing ever lasts forever," he continues. "Things change."