Ranking the Greatest Moments of Undertaker's WWE Career

On November 22, 1990, The Undertaker walked the aisle for his first WWE match, and in the 28 years since then, he etched his name in the history books as one of the greatest and most iconic Superstars to ever compete in Vince McMahon's rings.

From the early years as an enigmatic presence to his demonic Lord of Darkness phase to the American Badass and back again, he has captivated fans with moments and matches that have immortalized him.

In celebration of his anniversary with the company that made him a household name, relive these moments that have helped define his legendary career.

Though the list could be endless, these are most representative of his career as a whole.

8. The Resurrection of the Dead Man

At Royal Rumble 1994, Undertaker challenged Yokozuna for the WWE Championship in a Casket match. So unstoppable was The Deadman that it took 10 other vile villains to trap him inside the casket and secure the champion's successful title defense.

As they wheeled the casket out of the arena, thunder rolled, and on the giant video screen came a closeup of Undertaker. Appearing to be coming from inside the casket, he cut a poetic promo on his assailant, vowing never to rest in peace.

From there, he levitated out of the screen and into the heavens.

Yes, out of the screen and into the heavens, despite being in the casket.

It was completely absurd, but the character of The Undertaker was absurd. A living deadman wrestling every week? Ridiculous. It fit the character, though, and was responsible for a moment that is as memorable today as it was when it happened.

The stuff of YouTube legend.

7. The End of an Era

WrestleMania 28 may have been headlined by The Rock vs. John Cena, but the battle between Undertaker and Triple H inside Hell in a Cell, in a match dubbed "End of an Era," remains the night's best and most memorable bout.

With Shawn Michaels as the guest referee, four years' worth of WrestleMania epics combined into one classic match that both lived up to the lofty expectations set for it and solidified The Phenom, The Game and The Heartbreak Kid as three of the great storytellers in the long and illustrious history of professional wrestling.

Dramatic near-falls, crowd-popping spots and callbacks to previous bouts fueled the acclaimed match en route to Undertaker defeating a defiant Triple H and extending his undefeated streak at The Show of Shows.

Recently, we have seen the combatants take to the squared circle again in an attempt to recreate the magic they delivered that night in Miami, to no avail. Age and a lack of emotion behind their rivalry rendered their latest matches inferior. In the process, it only served to enhance the greatness and significance of that match.

Of the hundreds of matches those two Superstars had with each other, they had never (and likely will never) have another that reached that overall quality. A lot of that can be attributed to the connection the fans had with them and the aura of The Deadman's (at the time) undefeated WrestleMania streak. 

6. Royal Rumble Winner

Prior to January 2007, Undertaker had accomplished everything there was to accomplish in his Hall of Fame-worthy career. Everything but win the Royal Rumble.

That changed on January 28, 2007, when he entered the Rumble at No. 30 and became the first Superstar in the match's illustrious history to win from that spot.

To do so, he had to overcome the united front of Edge and Randy Orton, then spar with Shawn Michaels in one of the most exciting and breathtaking finishes in match history.

He crushed the dreams of Michaels, eliminating HBK in front of his hometown fans in San Antonio.

The Phenom stood tall as pyro exploded, with his spot in a championship bout on the stage he had dominated for so long secure.

5. His First WWE Championship

One year after making his WWE debut, Undertaker returned to the Survivor Series pay-per-view extravaganza for a date with the industry's biggest star, Hulk Hogan, for the WWE Championship.

Most figured The Deadman would go the way of King Kong Bundy, Earthquake, Big John Studd and the many other unstoppable big men who were set up only to be felled by The Hulkster.

That is not at all what happened.

So fresh, unique and convincing was the character that a segment of the fans in Detroit cheered him in his battle with The Immortal One. When Ric Flair appeared at ringside, it appeared as though Hogan would overcome the odds once more, but he did not.

Undertaker dropped him with a Tombstone on a steel chair, and three seconds later, he collected his first WWE Championship in a stunner of a finish.

Just one year after an auspicious debut, the man who was midcard fodder in WCW as Mean Mark had captured the top prize in sports entertainment–even if his reign was to be short-lived.

4. A Menacing Debut

"Million Dollar Man" Ted DiBiase promised a mystery partner for his team at the 1990 Survivor Series event, and after much speculation, the WWE Universe was treated to one of the most unforgettable and iconic arrivals in company history.

Stalking toward the squared circle with little emotion on his face but with the purpose of a predator eyeing its prey, The Undertaker captivated fans right out of the gate as he joined DiBiase, Greg Valentine and The Honky Tonk Man as they battled Bret Hart, Jim "The Anvil" Neidhart, Koko B. Ware and Dusty Rhodes in a tag team elimination match.

His presence and aura were enough to keep fans interested. The dominance he unleashed over the span of his stint in the match only served to ensure he would be one of the most talked-about Superstars on the loaded roster.

The impression the Deadman left on fans, fellow Superstars and management that night set the tone for one of the most magical, mystical, dark, demented, celebrated and iconic careers in the annals of professional wrestling.

3. A Five Star Classic

WrestleMania 25 was the silver anniversary of the Showcase of the Immortals, an event that had become as synonymous with The Undertaker as any other Superstar.

His undefeated streak intact, he faced competition from the only other man who could lay claim to his crown as the most celebrated Superstar in event history: Shawn Michaels.

The Heartbreak Kid made it a goal of his to down the Deadman, add the first blemish to his win-loss schedule and cement his status as the undisputed Mr. WrestleMania.

Together, the all-time greats created magic in Houston's Reliant Stadium, delivering a five-star classic that immediately entered the discussion for greatest match of all-time.

Utilizing dramatic near-falls to keep fans guessing as to who would leave victoriously, despite all signs pointing to an obvious Undertaker victory, the Superstars wowed even the harshest of critics with a breathtaking display of storytelling and performance art.

In the end, a top rope moonsault from Michaels landed him in the arms of The Deadman, who planted him with his second Tombstone piledriver and scored another impressive WrestleMania victory.

Over the course of his career, Undertaker was celebrated as one of the best big men to ever lace up a pair of boots, but he was missing that one match, devoid of gimmicks, that proved to the world his undisputed greatness.

On that night, he attained it.

And he did so again the following year with the same dance partner on the same grand stage.

2. THAT Hell in a Cell

There are many who will look at the Hell in a Cell match between Undertaker and Mankind at King of the Ring 1998 as a defining moment in the career of Mick Foley.

Upon further review, it is a landmark moment in the career of his opponent, who showcased an edgier, more violent and unforgiving part of himself fans had not previously been exposed to.

At the onset of the Attitude Era, it was an important moment for a character who could still be irresponsibly labeled as the same gimmicky, cartoonish nonsense that doomed WWE to mediocrity. He needed a spark that endeared him to a growing and evolving audience.

As he had done in the past, he did what was necessary to create excitement about himself and his character at a time when there was a ton of internal competition to be the best at the top of the card.

The lack of empathy for Mankind as he repeatedly threw him off and through the Hell in a Cell structure remains as haunting as the images of Foley recovering to fight some more.

In what was a banner year for Undertaker in 1998, the classic against Foley propelled him forward and into his WWE title program with Steve Austin just in time for their SummerSlam showdown entitled "Highway to Hell." 

1. The End of the Streak

Winning streaks in pro wrestling are not uncommon. They are oftentimes utilized to help build a young act up or create some sort of monster showdown between the unstoppable force and immovable object.

Then there was The Undertaker's undefeated WrestleMania streak, which sat at 21-0 entering New Orleans for the Showcase of the Immortals on April 6, 2014. It had grown into a mystifying beast, a tradition of the annual extravaganza and a drawing point even greater than championships.

It is for that reason that his loss to Brock Lesnar at WrestleMania XXX made the wrestling world stand still.

The sound of the referee's hand slapping the mat for the third time. The visual of Undertaker lying flat on his back in the center of the ring and graphics touting the 21-1 record on video screens hanging high overhead like dark clouds were haunting. The last gunfighter in WWE had suffered his greatest defeat on a stage he had helped legitimize.

So unexpected was it that mainstream media picked up on it. The topic of Undertaker's defeat dominated on social media. Fans cried, damning WWE for ruining their childhoods. It was, like the man himself, a phenomenon that encompassed the industry for weeks afterwards, and it still draws questions as to whether management made the right decision.

Rarely is a loss considered a wrestler's greatest moment, but to exclude that unforgettable event from any countdown detailing Undertaker's iconic career would be irresponsible.