In June of 2020, The Undertaker indicated as part of his documentary series Undertaker: The Last Ride that he had nothing left to prove in the ring after an iconic 30-year career. Is he retired for good or might The Dead Man ride again?

The Undertaker has been one of wrestling's all-time biggest attractions. Not only did he boast an unprecedented winning streak at WrestleMania, The Phenom also captured seven World Championships, participated in numerous Matches Of The Year, and headlined more big events than arguably anyone else in the business. Along the way, The Undertaker created several lasting memories that aren't likely to fade away any time soon.

 

In selecting the Top 50 Undertaker Moments, Wrestling Merchandise and Memories looked at the following criteria:

 

  • How unique was the moment?

  • What impact did it ultimately have on The Undertaker (and other people's) career?

  • What legacy does it have within the wrestling industry?

 

Questions? Feedback? Comments? As always, we want YOU to be a part of the conversation! Leave a comment below, or let us know on Twitter (@CanadianBulldog) using the hashtag #Top50. 

 

Ready? Here we go!

50.

Dead Man's debut

The Undertaker made his debut at the Survivor Series on November 22, 1990, as the mystery partner for The Million Dollar Man Ted DiBiase, The Honky Tonk Man and Greg The Hammer Valentine. While The Dead Man wasn't victorious, he did eliminate future WWE Hall of Famers Koko B. Ware and Dusty Rhodes.

48.

The Brothers of Destruction unite

Kane debuted in 1997 as The Undertaker's long-lost brother, leading to one of the biggest feuds in WWF/E history. By the summer of 1998, they put their differences aside to form The Brothers of Destruction tag team. Although it was an off and on relationship, the two captured three sets of tag team titles.

46.

The towering inferno

The long-standing feud between The Undertaker and his brother Kane took a strange turn at 1998's Unforgiven pay-per-view. The two faced off in the WWF's first-ever Inferno Match, in which a stream of fire surrounded the ring. The Dead Man won the match by pushing Kane into the fire and his arm catching ablaze.

44.

WrestleMania the 13th

In a nod to the horror movie franchise of a similar name, The Undertaker referred to his 1997 WWF World Title match as WrestleMania The 13th. Facing Sycho Sid in the main event of WrestleMania XIII, The Undertaker was able to overcome the odds and pinned Sid to win his second WWF Title.

42.

Kurt's angle

The Undertaker had several run-ins with WWE Hall of Famer Kurt Angle, including their Match Of The Year candidate at 2006's No Way Out. But the bad blood between the two began in 2000, after Angle accidentally spilled milk all over Undertaker's motorcycle, leading to a trio of PPV bouts during that year.

40.

A giant challenge (part 1)

Much of The Undertaker's early WWF career was battling huge men such as King Kong Bundy and Kamala. But none compared to the "nearly 8 foot tall" Giant Gonzales, who attacked Undertaker at the 1993 Royal Rumble. The Phenom defeated Giant Gonzales at that year's WrestleMania and SummerSlam.

38.

Betraying The Snake

As previously mentioned, The Undertaker and Jake The Snake Roberts were involved in a feud with Randy "Macho Man" Savage. Following the February 8, 1992 edition of Saturday Night's Main Event, Roberts planned to attack Savage's manager Miss Elizabeth. The Undertaker stopped him, leading to a new feud.

36.

Hogan's day of Judgment

WWE Hall of Famer Hulk Hogan has had several clashes with The Undertaker; their most recent one came in 2002 after Hogan returned to WWE. After capturing the Undisputed World Championship, The Hulkster defended it against The Undertaker at that year's Judgment Day and quickly lost the title.

34.

Punking out Punk

CM Punk's final appearance at WrestleMania was a challenge to The Undertaker to a match leading into WrestleMania XXIX. To get under his opponent's skin, Punk mocked the recent real-life death of Undertaker's long-time manager Paul Bearer. Revenge was served when The Undertaker prevailed.

32.

Hardcore Phenom

After turning heel in late 2001, The Undertaker began referring to himself as Big Evil, cutting his trademark long hair short and showing off his many arm and neck tattoos. The new persona culminated in a match at that year's Vengeance PPV, where he defeated Rob Van Dam for the Hardcore Title.

30.

Boiler Room Brawl

The rivalry between The Undertaker and WWE Hall of Famer Mankind took a strange turn during their Boiler Room Brawl at SummerSlam 1996. The cinematic match started backstage, with the first person to retrieve Undertaker's urn winning. When Undertaker went to obtain the urn, Paul Bearer turned on him.

28.

Legend vs. Legend Killer

Randy Orton was climbing the ranks through WWE as The Legend Killer, when the Raw star crossed over to SmackDown to challenge The Undertaker to a match at WrestleMania XXI. Orton turned heel again to give extra meaning to the match, and while he lost, it led to a prolonged feud against The Undertaker.

26.

Brock in a Cell (part 1)

The Undertaker had been feuding with WWE Champion Brock Lesnar for several months when The Next Big Thing challenged him to a Hell In A Cell match at 2002's No Mercy pay-per-view, which was one of Undertaker's specialty matches. Lesnar ended up winning the Cell match and the feud -- at that time.

24.

Respect for Jeff Hardy

The Undertaker was WWE Undisputed Champion and a heel when he battled Jeff Hardy in a series of matches. Their rivalry culminated with a ladder match on the July 1, 2002 edition of Raw. Even after losing the match, Hardy kept coming back, prompting The Dead Man to shake his hand and turn babyface.

22.

Crucifiction 3:16

As part of The Ministry Of Darkness storyline, The Undertaker targeted WWE Hall of Famer Stone Cold Steve Austin. Although they clashed several times, the most iconic moment of this point in time was on December 7, 1998 during Raw, when Undertaker crucified Austin on my "symbol" and raised it high in the air.

20.

Rated R tap out

The final time The Undertaker won a title at WrestleMania, it was at WrestleMania XXIV, where he was pitted against WWE Hall of Famer Edge. The Rated R Superstar was World Champion and had been involved in a series of run-ins with The Dead Man. Undertaker won the title via submission, a rarity.

18.

Phenom/Beast rematch

Following his historic loss at WrestleMania XXX to Brock Lesnar, The Undertaker waited more than a year to challenge The Beast Incarnate to a rematch. Their bout took place at SummerSlam 2015 and in a controversial finish, The Phenom appeared to tap out but still managed to knock Lesnar out.

16.

Highway to Hell

One of the biggest singles matches during The Attitude Era pitted WWE Hall of Famer "Stone Cold" Steve Austin against The Undertaker. Both fan favorites, they even briefly held the WWF Tag Team Titles together leading into the match. While Austin won, it was a huge moment for both competitors.

14.

Besting Batista

The Undertaker's 2007 Royal Rumble victory gave him the opportunity to face the WWE, World or ECW Champion at WrestleMania. The Dead Man chose World Champion Batista, leading to their title match at WrestleMania XXIII. The Undertaker won the title while preserving his streak.

12.

"I will not... Rest In Peace"

One of the strangest moments in The Undertaker's career came in 1994, when he faced WWE Hall of Famer and WWF World Champion Yokozuna at that year's Royal Rumble. A dozen heels trapped Undertaker in his own casket, at which point he appeared to ascend to the sky, saying he wouldn't rest in peace.

10.

Game Over (part 1)

The Undertaker's trilogy of WrestleMania matches against WWE Hall of Famer Triple H began at WrestleMania XVII, when The Game was still an up and coming heel trying to secure a main event spot. A year before WWE began formally acknowledging his WrestleMania streak, The Undertaker defeated Triple H.

8.

Game Over (part 3)

One year later, The Undertaker returned to WWE and, in a very similar scenario, challenged Triple H to a rematch at WrestleMania XXVIII. This match would be contested in Hell In A Cell, with Shawn Michaels as referee. The end result was the same, with The Undertaker extending his WrestleMania streak to 20-0.

6.

Roman takes the yard

The main event of WrestleMania XXXIII saw The Undertaker take on Roman Reigns. For only the second time in history, The Dead Man lost a match at WrestleMania. Afterwards, The Phenom neatly removed his gloves, hat and jacket and left them in the ring, suggesting his career was over.

4.

Raising Kane

October 5, 1997 was significant in the career for The Undertaker because of two moments. He wrestled Shawn Michaels in the first ever Hell In A Cell match. But it also signified the arrival of Kane, who tore the cage door down and confronted his brother, costing The Undertaker the match and creating a top WWE rivalry.

2.

End of The Streak

WrestleMania XXX signified the end of an era, as The Undertaker's unprecedented winning streak came to an end at the hands of Brock Lesnar. In a match that lasted 25 minutes, The Undertaker received three F5s and finally succumbed to Lesnar, turning his incredible 21-0 winning streak at WrestleMania to 21 wins and 1 loss.

49

Burying Bearer

A very unusual (yet memorable) moment happened at The Great American Bash in 2004. Facing The Dudley Boyz, a stipulation was made that The Undertaker's manager Paul Bearer would be buried in a vat of cement if he didn't throw the match. The Undertaker won... and then buried Bearer in the cement.

47.

Teaching Cena respect

One of John Cena's first rivalries was against The Undertaker. As a brash, arrogant heel, Cena began mocking The Dead Man during various episodes of SmackDown, running him down. Insitsing he would teach Cena respect, the two had a match at 2003's Vengeance pay-per-view, which The Undertaker won.

45

Putting JR in his place

On the November 26, 2001 edition of Raw, WWE Hall of Famer Jim Ross became the second inductee into the Vince McMahon Kiss My Ass Club. When JR tried to resist the "honor," The Undertaker arrived. Instead of defending Ross, The American Bad Ass turned heel, and forced JR to "pucker up."

43.

Wedding crashers

In the summer of 1991, The Undertaker formed an unholy alliance with WWE Hall of Famer Jake "The Snake" Roberts. Following the wedding of Randy "Macho Man" Savage and Miss Elizabeth at SummerSlam, Roberts and The Dead Man crashed the wedding reception, planting a cobra and assaulting Macho Man.

41.

Dethroning Diesel

Some 21 years before Roman Reigns challenged The Undertaker for being the baddest dog in the yard, The Dead Man was challenged at WrestleMania XII by WWE Hall of Famer Diesel. The two had an intense rivalry leading into WrestleMania, when The Phenom added Big Daddy Cool to his iconic streak.

39.

A giant challenge (part 2)

More than a decade later, history repeated itself when the 7"1 tall Great Khali arrived in WWE and attacked The Undertaker on the April 7, 2006 edition of SmackDown. While Khali pinned The Dead Man in their first meeting, leading to a Last Man Standing match later that summer, where Undertaker won the bout.

37.

Boss Man's execution

In 1999, The Undertaker began assembling a group to take down Vince McMahon's Corporation. Part of that took place at WrestleMania XV, when The Dead Man battled WWE Hall of Famer Big Boss Man in a Hell In A Cell match. The bout concluded with Undertaker "hanging" Boss Man by a noose.

35

Shane in a Cell

Another one of The Undertaker's Hell In A Cell matches took place at WrestleMania XXXII, where The Dead Man took on the returning Shane McMahon, with the stipulation that if Undertaker lost, it would be his final Mania appearance. The Phenom rallied and defeated Shane O'Mac in a thrilling cage match.

33.

The American Bad Ass

Over the years, The Undertaker has taken several hiatuses to keep healthy and keep his persona fresh. After walking away from the company in late-1999, The Undertaker returned at the Judgment Day 2000 pay-per-view with a new persona, dressed in biker gear and coming to the ring to Limp Bizkit's "Rollin'".

31.

WrestleMania return

After being humiliated by Vince McMahon and his brother Kane the previous winter, The Undertaker returned to action at WrestleMania XX to battle his estranged sibling. But instead of wearing his biker gear, The Undertaker went back to his roots, wearing mortician clothes and having Paul Bearer by his side.

29.

Boneyard Match

The Undertaker participated in another cinematic match, this one nearly 25 years later at WrestleMania XXXVI. The Dead Man met AJ Styles in a Boneyard Match, which included the two man battling on top of the roof of a creepy house and Undertaker literally burying Styles in a grave before riding off into the darkness.

27.

Hart and Soul

One of the biggest WWF World Championship matches in SummerSlam history, The Undertaker defended against WWE Hall of Famer Bret Hart. If Hart lost, he would have never been allowed to wrestle in the U.S. again. Thanks to accidental help from Shawn Michaels, Hart won and captured the title belt.

25.

Brock in a Cell (part 2)

Thirteen years after their first Hell In A Cell encounter, The Undertaker and Brock Lesnar had a rematch in the same struture at the aptly-named Hell In A Cell pay-per-view. The final contest in a three-match series between them since 2014, Lesnar won again by dropping The Phenom with an F5 to the ring floor.

23.

The Ministry of Darkness

When The Undertaker turned heel in 1998, he began a faction called The Ministry Of Darkness that had Satanic overtones. The group, which debuted on the October 19 edition of Raw, included WWE Hall of Famers Paul Bearer, Faarooq and Edge, as well as Bradshaw, Christian, Viscera, Mideon and Gangrel.

21.

"Where to, Stephanie?"

At the conclusion of 1999's Backlash PPV, Stephanie McMahon was escorted into a limousine so she wouldn't be targeted by The Undertaker's Ministry Of Darkness. But The Phenom comandeered the vehicle, kidnapping Stephanie and attempting a forced marriage the next night on Raw, where she was rescued by Steve Austin.

19.

Chokeslam to Hell

Following WrestleMania XXIV, The Undertaker and Edge continued to feud throughout the year, culminating in a Hell In A Cell match at SummerSlam 2008. No longer champion, Undertaker won the match with a tombstone and followed up by chokeslamming Edge off a ladder and right through the ring!

17.

Buried Alive

The Undertaker was looking forward to finally silencing his boss, WWE Chairman Vince McMahon, during their Buried Alive match at the 2003 Survivor Series. Just when it appeared that The Dead Man had things at hand, Kane resurfaced and helped McMahon bury Undertaker and win the match.

15.

Reaper's Rumble

Despite being in WWE for more than a quarter-century and often main-eventing top shows, The Undertaker has only won the Royal Rumble one time. That happened in 2007, when The Dead Man ousted MVP, The Great Khali and runner-up Shawn Michaels on route to winning that year's Rumble match.

13.

The Ultimate burial

The Undertaker's first major rivalry was with WWE Hall of Famer The Ultimate Warrior. In the aftermath of WrestleMania VII, The Warrior appeared on Paul Bearer's Funeral Parlor talk show. Ultimate Warrior was ambushed by The Undertaker who, along with Bearer, locked him up in an "airtight" casket.

11.

Undertaker vs. Undertaker

Following the 1994 Royal Rumble, The Undertaker stayed buried for nearly six months. He returned at that year's SummerSlam to confront.... The Undertaker, an impostor managed by The Million Dollar Man Ted DiBiase. At SummerSlam, the legit Undertaker sent to his doppelganger back to Parts Unknown.

9.

Game Over (part 2)

Exactly ten years later, The Undertaker and Triple H both returned to Raw in the very same segment and challenged each other to a match at WrestleMania XXVII. Their No Holds Barred match had a big fight feel, with a possibility that The Game could end Undertaker's streak, but alas, The Undertaker prevailed.

7.

Who is Mr. WrestleMania?

After years and years of boasting that he was Mr. WrestleMania, WWE Hall of Famer Shawn Michaels was put to his biggest test in 2009 when he challenged The Undertaker at WrestleMania XXV. With The Undertaker's streak hanging in the balance, HBK lost to The Dead Man in a Match Of The Year winner.

5.

The Gravest Challenge

One year after his debut, The Undertaker was main-eventing the 1991 Survivor Series against WWE Hall of Famer and WWF World Champion Hulk Hogan. Thanks to interference from Ric Flair, Undertaker tombstoned Hogan, capturing the first of many WWF/E World Championships.

3.

Mankind goes to Hell

Following 1997, The Undertaker's next (singles) Hell In A Cell was at the King of the Ring in 1998, where he faced WWE Hall of Famer Mankind. After tossing Mankind both off and through the Cell structure, The Phenom broke his ankle by jumping down to the ring, ending one of the most brutal matches in WWE history.

1.

Heartbreak for HBK

Following his first WrestleMania victory over WWE Hall of Famer Shawn Michaels, The Heartbreak Kid demanded a rematch. After much soul-searching, The Undertaker agreed, but only if Michaels put his career on the line. HBK agreed, and the rematch was set for WrestleMania XXVI. In arguably the greatest match in WWE history, The Undertaker not only turned back Shawn Michaels's challenge but was able to retire Mr. WrestleMania.

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Wrestling Merchandise and Memories podca
Wrestling Historian Mike Rickard