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On any list of the greatest WWE superstars of all time, you’ll find the Undertaker. Mark Callaway first wrestled in the WWF as the “Deadman” in 1990 and retired from the ring in 2020. In 2022, he became a member of the WWE Hall of Fame.

The Undertaker’s A&E Biography: WWE Legends kicked off season two of the popular TV series, and, afterward, he sat down with host Peter Rosenberg to discuss his life and times in pro wrestling.

In his 30-year career, The Undertaker has had more matches, feuds, and rivalries than most in pro wrestling. However, there were a few that stood out more than others. In his chat with Rosenberg, The Undertaker revealed the three feuds (with four superstars) that meant the most to him.

1. Kane vs. The Undertaker

I think Kane and I both will tell you that we feel like that story — the Kane and Undertaker story — is probably the greatest story ever told in wrestling. It’s up there. There’s so many layers to it. 

The Undertaker on his proram with Kane

When wrestling fans think of The Undertaker, the first program that comes to mind is his decades-spanning relationship with his rival, friend, partner, (kayfabe) half-brother, Kane.

The Undertakers’ ring name was originally Kane the Undertaker before he dropped the Kane for the shorter version. In 1997, Takers’ presumed-dead half-brother Kane showed up with valet Paul Bearer, and the two started one of the most memorable feuds in WWE history.

A year later, the two teamed up as The Brothers of Destruction and multiple tag-team titles together. The rivalry/partnership dynamic would go back and forth all the way to The Undertakers’ retirement.

2. The iconic Mick Foley Hell in a Cell match

It’s hard not to say my rivalry with Mick [is one of the best]. I mean, we did so many innovative things.  

The Undertaker on his iconic match with Mankind

One of the most memorable feuds early in The Undertaker’s career was with Mick Foley as Mankind. The scary, chiseled 6-foot-10 Undertaker and schlubby, silly, masked Mankind made for an interesting pairing. Working together in the ring, though, the duo was explosive.

In one of the most iconic matches in WWE history, the two fought in a Hell in a Cell cage match during the King of the Ring pay-per-view in June of 1998.

The match started with a brawl on top of the 16-foot cage, and The Undertaker threw Mankind off the top of the structure and onto the Spanish announcers’ table below. The voice of the WWE, Jim Ross, famously screamed, “Good God almighty! Good God almighty! They’ve killed him!”

After medical attention, Mankind fought his way off a stretcher and returned to face The Undertaker on top of the cage. Taker choke-slammed his opponent at one point, and the cell gave way, sending Mankind to the mat below and (really) knocking him unconscious.

Foley once again recovered and finally lost the match when The Undertaker delivered his signature Tombstone Piledriver.

3. Four ‘WrestleMania’ matches with Sean Michaels and Triple H

Triple H and The Undertaker battle during their WWE match at 'WrestleMania 27'.
Triple H and The Undertaker | Moses Robinson/Getty Images

To tie everything together, the four matches I had with Sean [Michaels] — the two with Sean, then the two with Triple H — I think are probably some of the best work that I did in my career. To be able to tell a story for over four years, four WrestleManias in a row. Because if you watch it, the first match leads into the retirement match, and then you have the buddy trying to take up for his friend. Then Triple H — I win the match, but he leaves me laying like no one’s ever seen me, not able to get up — which leads to ‘Hell in a Cell’, end of an era. I’m really, really proud of that. 

The Undertaker on his four WrestleMania matches with Sean Michaels and Triple H

One of The Undertaker’s biggest claims to fame is his streak of 21 consecutive WrestleMania victories. His 17th and 18th victories came against Sean Michaels, and his 19th and 20th wins were vs. Michaels’ best bud Triple H, in WrestleMania 25 through 28.

The storytelling in this tetralogy is top-notch, as The Undertaker explains in his own words above. Each match was over 20 minutes long, with two cresting the half-hour mark.

The Undertaker, Heartbreak Kid, and The Game are three of the most influential WWE superstars of all time, and the finale of this feud at WrestleMania 28 (2016) in a Hell in the Cell match vs. Triple H with Michaels as guest referee stands out as the true bow on top of an era in pro wrestling.

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