For all but two years of my life, The Undertaker has been a major player in WWE. From his debut at the 1990 Survivor Series to his shockingly fun Boneyard Match against AJ Styles at WrestleMania 36 in 2020, the Deadman, Phenom, American Badass, or any other nickname he's used over the course of this 30-year career, Mark Calaway was always one of the best, if not the best wrestler to watch on any given pay-per-view, Monday Night Raw (and Smackdown), or house show.
My childhood, adolescence, and even young adulthood were filled with memories and matches involving The Undertaker, and now that he's finally retiring (officially this time) from the sport of professional wrestling, there's never been a better time to look at the 10 best moments from the future WWE Hall of Famer's decades-long career inside the confines of the squared circle. With championship victories, the impressive "Streak," and other awe-inspiring moments, there's a lot to cover, so let's get to it before The Undertaker changes his mind and puts on one more match.
10. The Undertaker Takes On AJ Styles In A Boneyard Match At WrestleMania 36
We'll start things off with The Undertaker's Boneyard Match against AJ Styles at WrestleMania 36 in April 2020. This is a case where WWE and all involved parties turned lemons into lemonade after the Coronavirus pandemic forced the promotion to hold the annual spectacle behind the closed doors for the first time in WrestleMania history. Instead of giving fans an awkward traditional match in an empty studio, Taker and Styles went all-in on the "Boneyard Match" concept and created something that was equal parts wrestling and early-90s horror action goodness. It's like if Walker Texas Ranger and John Carpenter's Halloween were put into a blender.
9. The Undertaker Pays Respect To The Recently Deceased Paul Bearer At The 2014 Hall Of Fame Ceremony
In the early days of The Undertaker's career, he was accompanied to the ring each night by the late Paul Bearer. Known for his unnaturally high-pitched voice, dramatic makeup, and the urn of ashes he carried tightly in his hands, Bearer helped make Taker a superstar. Tragically, Bearer passed away after suffering a heart attack in early 2013 and was inducted into the WWE Hall of Fame one year later one night before WrestleMania 30. During the ceremony, The Undertaker appeared on stage and provided an unspoken yet highly emotional tribute to his former mentor and friend, giving fans a moment they'll never forget.
8. The Deadman Returns At WrestleMania 20
Starting in May 2000, The Undertaker abandoned his "Deadman" gimmick for the American Bad Ass character that seemed to better represent who Mark Calaway was a person. And while it was great to see Taker learn a few new moves (a variant of the classic powerbomb), fans were ready to see the classic Undertaker of the past to return. And those fans got their wish at WrestleMania 20 in 2004 when the Phenom returned to take on Kane (more on their history later). The match isn't anything to write home about, but it did mark the return of one of the greatest characters in the history of wrestling.
7. The Undertaker Throws Mick Foley Off The Hell In A Cell At King Of The Ring 1998
You can't watch any best-of compilation from the Attitude Era or the respective careers of The Undertaker and Mick Foley without seeing at least one shot from their infamous Hell in a Cell match at the King of the Ring pay-per-view in June 1998. Without even watching the footage I can see and hear the moment Taker throws Foley from atop the structure onto the announce table 15 feet below. The gasp of the crowd, the crash of the table, and the image of Undertaker standing alone on the cage play in my head all the time.
6. The Undertaker Begins A Feud With His Long-Lost "Brother" Kane At Badd Blood 1997
A little less than a year before The Undertaker threw Mick Foley off the Hell in a Cell structure, he came face to face with his long-lost "brother" Kane at the In Your House: Badd Blood event in October 1997. Partway through Taker's number-one contender match against Shawn Michaels, Kane forced his way into the steel structure, confronted his brother for burning him alive, and cost him a title opportunity. The two giant wrestlers would feud leading up to WrestleMania 14, but the "Brothers of Destruction" would cross paths — both as allies and enemies — numerous times in the following years.
5. The Undertaker's Debut At Survivor Series In 1990
The 1990 Survivor Series will go down as one of the most consequential events in WWE history simple because it served as the stage for one of the biggest debuts in the final decade of the 20th Century. No, not the Gobbledy Gooker who also made its television debut that night. I'm talking about The Undertaker who served as the mystery member on The Million Dollar Team in one of the night's Survivor Series elimination matches. Watching a young Undertaker with ashen skin and an outfit that looks like an Old West mortician, you can't help but see the future in one-day Phenom. And this was just the beginning.
4. The Undertaker Defeats Hulk Hogan For The WWE Championship At Survivor Series 1991
Nearly one year to the day after making his WWE debut at the 1990 Survivor Series, The Undertaker won his first WWE Championship at the 1991 Thanksgiving Eve pay-per-view in a match against Hulk Hogan. Despite having a convoluted ending involving interference by Ric Flair, the win cemented Taker's place in the WWE history books and also added stakes to the 1992 Royal Rumble Match, or as I like to call it, the greatest night in WWE programming. The Undertaker would secure the top honors in the company a few more times throughout his career, but none held a candle to another aspect of his career.
3. The Undertaker Begins "The Streak" With A Win Over Jimmy Snuka At WrestleMania 7
Even though The Undertaker only had a handful of WWE Championship reigns throughout his career, he did have something that no one before him or since has had: a 21-0 winning streak at WrestleMania. Before Brock Lesnar ended "The Streak" at WrestleMania 30 in 2014, Taker hadn't lost a match at the Showcase of the Immortals since his first Mania match against Jimmy "Superfly" Snuka at WrestleMania 7 in 1991. The Undertaker was only a few months into his WWE career when he was put up against Snuka, who had been a major player in the industry for years at that point, so having a young wrestler gain a decisive victory was a major step in his career.
2. The Undertaker Leaves His Signature Hat And Duster In The Ring At WrestleMania 33
In the years following the end of "The Streak," The Undertaker continued to have matches at the annual event, but none had the gravitas and impact as the Deadman's match against Roman Reigns at WrestleMania 33. Everything from the lead-up to the execution of the match made this one seem like it was going to be the last time anyone would see Taker in the ring, and that was only strengthened when he folding his iconic coat and placed it along with his hat in the center of the ring. If that were the case, this moment would be in the top spot of this list, but the continuation of Taker's career knocked it back a spot.
1. The Undertaker Puts The Streak On The Line Against Shawn Michaels At WrestleMania 25
And then there's the best Undertaker match of all time — his one-on-one against Shawn Michaels at WrestleMania 25 in 2009. Hosted in both wrestler's home state of Texas, this 30-minute barnburner of a match saw the two aging stars put it all on the line as they became immortals in the process. In the weeks leading up to the match, Taker and the Heartbreak Kid added elements of their past interactions (both in-ring and backstage) to create this career-spanning epic that could have gone either way. The two legends traded finishing moves before The Undertaker finally put an end to it with a Tombstone Piledriver. And although the two would meet again the following year, nothing compares to the uncertainty and electric chemistry of this match.
There are many more memories from The Undertaker's legendary career, but I couldn't bring myself to include the time Taker kidnapped Stephanie McMahon, or when he tried to embalm Stone Cold Steve Austin, or the time his motorcycle stalled out on the top of the ramp. All kidding aside, The Undertaker has been a major part of wrestling and the lives of his fans for 30 years now and his retirement leaves a major hole in the sport of professional wrestling.
