The Undertaker's Most Memorable Matches, Moments in WrestleMania History

Since the event's inception in 1985, no wrestler has been more synonymous with WrestleMania than The Undertaker.

Sure, WrestleMania probably wouldn't be where it is without Hulk Hogan, and plenty of other stars helped lay the groundwork for the success WWE enjoys today. But nothing can top Undertaker's undefeated streak, which lasted for more than two decades before Brock Lesnar ended it at WrestleMania XXX in 2014.

Even before WWE acknowledged his streak and made it one of the biggest stories at WrestleMania, The Deadman was routinely involved in the pay-per-view's biggest moments each year.

With The Undertaker's in-ring career winding down—and possibly over altogether—let's take a look back at his top highlights from the last 27 years.

WrestleMania VII: The Streak Begins

At the time, nobody could have possibly known what The Undertaker's win over Jimmy Snuka at WrestleMania VII in 1991 would mean from a historical perspective.

The fact he squashed Snuka in 4:20 did, however, indicate WWE was high on his potential. Eight months later, he beat Hulk Hogan for the WWF Championship at Survivor Series.

The commentary from this match is also a great example of putting over a wrestler who was still somewhat of an unknown to many wrestling fans.

Hearing Gorilla Monsoon and Bobby Heenan marvel at The Undertaker added to his mystique and helped him come off as an even bigger threat in the ring.

WrestleMania IX: The Undertaker Rides a Chariot at Caesars Palace

The Undertaker's win over Giant Gonzalez might be his worst WrestleMania match, and it came at WrestleMania IX, which is one of—if not the—worst Show of Shows WWE has put together.

Nobody expected The Undertaker to get a good match out of Giant Gonzalez, but the finish featured his opponent using a chloroform-soaked rag to draw a disqualification. It was the third marquee match on the card in which shenanigans were involved.

With all of that said, The Undertaker's entrance alone is worth going back and watching again.

This was the first time WWE went out of its way to give The Deadman an elaborate WrestleMania entrance—something that would become more commonplace in later years. Seeing him roll up in a black funeral chariot with a vulture by his side was an ominous sight.

WrestleMania XIV: The Undertaker Walks Through Fire to Face His Brother

Now, we move to what arguably remains The Undertaker's best WrestleMania entrance ever.

What this lacked in production value more than made up for with visuals. The Deadman walked to the ring while passing under a series of torches held by his druids.

From a technical perspective, The Undertaker vs. Kane wasn't a great match, but it told a pretty good story and made Kane look like good even in a losing effort. The Deadman needed three Tombstone Piledrivers to keep The Big Red Machine down for the three-count.

The bout was at least light years ahead of The Undertaker's victory over Sycho Sid at WrestleMania 13 a year earlier.

WrestleMania XV: The Ministry of Darkness Hangs Big Boss Man

The video above conveniently leaves out the moment almost everybody remembers from The Undertaker's win over Big Boss Man at Wrestlemania XV.

WWE's standards were a little looser in 1999, so chairman Vince McMahon apparently didn't think literally hanging a wrestler from the cell might be in poor taste.

After The Undertaker got the pinfall on his opponent, The Brood repelled down to the top of the cell from the ceiling of TD Garden. They then dropped a noose into the ring, which 'Taker placed around the Boss Man's throat.

Paul Bearer raised the cell enough so that Big Boss Man hung above the ring until the lights went out and somebody presumably cut him down.

This was undoubtedly memorable but not in a good way.

WrestleMania XXIV: The Undertaker Beats Edge to Win World Heavyweight Title

It was amazing to watch The Undertaker transform into one of the better technical wrestlers on the WWE roster later in his career.

Generally, legends start to slow things down when they get older. The Deadman, instead, decided to reinvent his in-ring self and do even more.

His WrestleMania 23 match with Batista was very good and emblematic of that shift, but his WrestleMania XXIV bout with Edge is superior.

Edge and The Undertaker continued to feud throughout 2008, but it wasn't until SummerSlam 2008 that they'd have another match that equaled their encounter in Orlando, Florida.

WrestleMania XXV: The Undertaker and Shawn Michaels Steal the Show

From start to finish, everything about this match is amazing.

During their respective entrances, Shawn Michaels descends from the heavens while The Undertaker ascends from the underworld. It's one of the best entrance sequences ever at WrestleMania.

Michaels also felt like somebody who could break the streak, which added to the drama. In almost every year before this, either the streak hadn't earned the gravitas it would later receive, or nobody seriously believed The Undertaker would lose to whoever his opponent was.

When Michaels kicked out of a Tombstone Piledriver—a touch made so much better by the camera zooming in on a mystified Undertaker—it felt like the streak might go down in flames.

Instead, The Undertaker caught Michaels as he was attempting a moonsault and countered it into another Tombstone Piledriver for the victory.

WrestleMania XXVI: The Undertaker Ends The Heartbreak Kid's Career

It says everything about this match that you could argue it's better than Undertaker vs. Michaels from a year earlier. The two were wrestling in the main event with sky-high expectations, and they more than delivered.

Michaels putting his career on the line also provided the necessary intrigue. No matter what happened, something historic was going down.

The finish was even a nice callback to WrestleMania XXV. The Undertaker knew a simple Tombstone Piledriver might not get the job done, so he went for a super-powered version of the move—jumping in the air before driving Michaels' head into the mat.

It proved to be the final match of Michaels' in-ring career.

WrestleMania 29: The Undertaker Defeats CM Punk in the Final Match of the Streak

In retrospect, this was the last match where The Undertaker could wrestle without noticeably showing his age, and it's easily the last really good WrestleMania match he has had.

During the weeks building up to WrestleMania 29, CM Punk and The Deadman walked a thin line between good storytelling and shamelessly cashing in on a real-life situation.

The Undertaker's persona has obviously always been tied to the specter of death, but it's different when an actual death in the real world become part of his character motivations. 

Punk pouring out Paul Bearer's kayfabe remains onto The Undertaker produced a great visual, yet contrasted significantly with the more tame angles that populate WWE programming.

WrestleMania XXX: The Streak Ends

A strong case could be made for this being the most disappointing match in WWE history—not just at WrestleMania.

WWE did little to make this feel like an important bout beyond just getting The Deadman involved. The story was rushed, and fans never got the impression The Undertaker's streak was in actual jeopardy—unlike a few of his matches in the years before.

There's also the question whether Brock Lesnar was the right guy to end the streak. Ending the run could've been a star-making moment for a younger wrestler who needed that last little push. 

Sure, beating The Undertaker made Lesnar look more of a monster, but he didn't need a ton of help in that regard.

WrestleMania 33: The End of the Deadman?

As divisive as Roman Reigns may be among members of the WWE Universe, him beating The Undertaker would have been a much more appropriate way to end The Deadman's WrestleMania streak.

At WrestleMania 33, he got the next best thing as he defeated The Deadman, who seemingly signaled his retirement by leaving his hat, gloves and coat in the ring. 

Reigns vs. 'Taker wasn't a great match on its own, though it largely achieved what it needed to, as the seven-time world champion passed the torch to The Big Dog.

The Undertaker gave a cryptic promo at Raw 25 that some read as him opening the door for a return. John Cena also issued a challenge to The Undertaker on Raw on Monday night, so he may not remain retired for much longer.