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The Undertaker’s 7 Best Wrestling Moments

The Undertaker’s 7 Best Wrestling Moments

On April 2 of this year, in the main event of Wrestlemania, the Undertaker wrestled his final match. Losing to Roman Reigns, Undertaker ended an almost 27-year odyssey that most professional wrestlers can only dream about. There were many iconic moments throughout his career that made “the Phenom” the greatest WWE superstar of all time. We’ve narrowed these moments down to arguably his top 7 (with SO much to work with, there will HAVE to be some debate). Let’s take a look at the storied career of “the Deadman.”

7. Retirement

Undertaker Retirement

While it may seem like someone ending their career shouldn’t be part of a “greatest moments” list, we are all about making exceptions. It wasn’t the fact that the Undertaker retired, it was HOW he did it. After losing to Roman Reigns, the Undertaker put back on his long black coat and hat. He then looked around CW Stadium at the over 70,000 people cheering for him. He then slowly walked to the middle of the ring and took off his gloves, hat, and coat. He walked out of the ring and up the ramp, giving one last fist to the sky to not only the fans live, but to the millions watching around the world. An hour after the event ended, as crews were tearing down the Wrestlemania set, the Undertaker’s “remains” still laid in the middle of the ring, being the last items removed as a sign of respect for the Dead Man.

6. Wrestlemania Series with Triple H, “End of an Era”

End of an Era

After facing Shawn Michaels at the previous two Wrestlemanias, the Undertaker fought Michaels’ best friend and D-Generation X teammate Triple H at the NEXT two. Their first match at Wrestlemania 28 took a heavy toll on the Undertaker. Even though he pulled out the victory, he had to be helped to the back, while Triple H was able to walk on his own. That didn’t sit well with the Undertaker, who asked for a rematch the following year. After weeks of saying no, Triple H finally accepted and upped the stakes by making it a “Hell in a Cell” match, a steel cage in which both superstars excelled. With Shawn Michaels as the special referee, Undertaker and Triple H tore into each other even more than they did the previous year. Undertaker would once again gain the victory, upping his Wrestlemania winning streak to an unbelievable 20-0. In a “Wrestlemania Moment” for the ages, the three legends walked up the ramp together, signifying the “end of an era.” Michaels was retired, and Undertaker and Triple H never wrestled a full-time schedule again.

5. Saving Miss Elizabeth From Jake Roberts (Undertaker becomes a Babyface)

When the Undertaker made his debut, he was a bad guy, or “heel.” With a character that was basically a giant mortician, it made sense. As time grew, fans began to be drawn to this character. Mark Calaway (his real name) was 100% committed to the character of the Undertaker that everyone bought it, no matter how crazy some storylines became. During this time, the WWE had a “Superman” in Hulk Hogan. What better use of the Undertaker than to be its “Batman.” A hero that uses the darkness as a force for good. This transition began in an episode of Saturday Night’s Main Event in 1992. Jake Roberts was about to hit Miss Elizabeth with a chair, and right as she and her husband Randy Savage entered the backstage, Jake swung back, only to have the chair caught by the Undertaker, to the surprise and delight of fans everywhere.

4. The Streak

WWE Superstars are lucky to have a career that spans 21 years TOTAL, let alone have one that allows them to win at the WWE’s Super Bowl 21 straight times. There’s not quite a star like the Undertaker though. Beginning with Superfly Jimmy Snuka and ending with CM Punk, the Undertaker’s streak at Wrestlemania is almost as, if not more, important than any of the championship matches at the event. It was never “Who is the Undertaker fighting at Wrestlemania?” It was always “Who is the Undertaker BEATING at Wrestlemania?” While the streak may have ended at Wrestlemania 30 at the hands of Brock Lesnar, it is a record that will stand for a LONG time.

3. Return of the Deadman

In late 2003, Kane defeated his brother the Undertaker in a “Buried Alive” match. For months, Kane gloated about destroying the legacy of his sibling. That’s why he was confused when it was announced he would be facing the Undertaker at Wrestlemania XX. The Phenom showed up, but without the motorcycle or headband. The original Undertaker had returned, with his manager Paul Bearer in tow (yes, PAUL. BEARER). While little things about his character would change during the rest of his career to stay current with the times, Undertaker never shed the Deadman gimmick again. This was what he was most comfortable with, and was the version of the character fans love.

2. Throwing Mankind off the Cell


No Undertaker list would be complete without arguably the most famous clip in WWE history. In 1998, the Undertaker was once again feuding with Mankind, and both aimed to settle their feud in a “Hell in a Cell” match. Like most of these matches, the action went to the outside of the cage, and then to the top. What NO ONE expected was how quickly Mankind would fall from the cage, as the Undertaker grabbed him and launched off the side and through a table. This incident solidified both Undertaker AND Mankind as certified badasses, as well as gave us one of announcer Jim Ross’ most famous quotes: “AS GOD AS MY WITNESS, HE IS BROKEN IN HALF!”

1. Wrestlemania 25: Undertaker vs. Shawn Michaels

Shawn and Taker

If you were to ask someone what the greatest match in Wrestlemania history is, most people would have answered Ricky Steamboat vs. Randy Savage from Wrestlemania III. That was until Wrestlemania 25 in 2009. Shawn Michaels fought the Undertaker in an instant classic. At 30:44, it was the longest match on the card. It was also the first time that fans thought the streak had a legitimate chance of coming to an end. From kicking out of the Tombstone piledriver to hitting his patented Sweet Chin Music (your basic kick to the face), Shawn Michaels gave the Undertaker everything he had. It was after the Undertaker caught Michaels mid-air during a backflip from the top rope and delivering another Tombstone did the Phenom seal the victory as well as end the successor to Steamboat/Savage as the greatest Mania match of all time.



The legacy of the Undertaker is one that will not only last forever within the WWE but within television as a whole. The character has been around since 1990, roughly just as long as the Simpsons. For a character to stay relevant for SEVEN years let alone 27 is quite a feat. The Undertaker was able to accomplish this. From being a mortician to a biker to a man with the powers of the dead, he captivated audiences for years, and his legacy will live on for years to come.

So what do you think? What is YOUR favorite Undertaker memory? Let me know on Twitter or rest…in….peace down in the comments below.

Images: WWE

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