He goes by many names - The Demon of Death Valley, The Reaper of Wayward Souls, The Conscience of the WWE, and The Phenom. Sure enough, The Deadman, The Undertaker isn't just a man of too many nicknames to print here, he's also the most legendary character every created in the industry. Debuting in the mid-eighties, WCW couldn't figure out a way to utilize the imposing big man (no shock there), so he would eventually head to the WWE, debuting at the 1990 Survivor Series and he immediately captivated the WWE Universe. It wasn't long before he'd become the most popular character in the company and perhaps the business.
Perhaps the greatest accomplishment in the history of this man is The Streak. While we all know the business is a work, for over 20 years, The Phenom was booked to win at the show of shows. What started as just an over guy staying over every year eventually morphed into an attraction, and as far as WrestleMania is concerned, The Deadman's appearance at the Showcase of Immortals became as important as the WWE Championship being defended. When it was finally broken by The Beast, Brock Lesnar in New Orleans, the crowd went (no pun intended) dead silent for what was thought at that time to be either the most shocking event ever in wrestling or the biggest botch ever.
In reliving The Streak, let’s rank each and every opponent of The Undertaker based on the significance they would play on his career.
Note: This piece is specific to The Undefeated Streak and will not include Bray Wyatt and Shane McMahon.
18 Giant Gonzalez (WrestleMania IX: 3-0)
Every betting and even non-betting person could've guessed this match would be ranked at the lowest spot on the countdown. Similar to Big Evil's WCW days, The Giant Gonzalez was not used properly. He came into to the WWE as one of Harvey Wippelman's monsters that was used to exact revenge on the 'Taker for how he buried Kamala. Debuting at the Royal Rumble in 1993, he destroyed and eliminated The Undertaker, costing him a chance at the WWE Championship. Starkly different than The Phenom though, was the fact that they were right to not know what to do with El Gigante, as the big guy couldn't work at all unfortunately. The match and the feud were unbearable, but were par for the course for the day, as they'd consistently set up The Phenom against other monsters. Literally the only thing memorable or noteworthy about this match is 'Taker's entrance complete with a vulture perched on his death chariot.
17 Big Show/A-Train (WrestleMania XIX: 11-0)
The monster party would continue throughout The Demon of Death Valley's epic run. Does anyone remember the seven foot Aussie, Nathan Jones? So for everyone but the two people who do, Nathan Jones was the kind of monster Vince McMahon fancies. Naturally that meant they paired the dude up with the best big man ever, The American Bad Ass, in some sort of protégé/protégée partnership. Hindsight being what it is, considering how quick Jones quit due to not being able to deal with the rigors of the road, we should have all realized how pointless this partnership was going to be.
Nevertheless the match was still booked for 'Mania at Safeco Field. Big Show and A-Train came gunning for The Deadman and Jones. At the last minute, however, it was decided that 'Taker would do battle with his foes in a Handicap match, as the grossly inexperienced Jones was written out of the match. While it's not shown the way The Phenom's Caesars Palace entrance is shown, this is the second entry on the list where the entrance is more memorable than the match. The American Bad Ass is played out by Limp Bizkit, and with the Iraq war looming, 'Taker rode out on his bike with Old Glory flying high. Simply because this match had the Big Show over Gonzalez, it gets ranked one notch higher.
16 King Kong Bundy (WrestleMania XI: 4-0)
After The Undertaker was "killed" by Yokozuna and 1,700 other heels at the 1994 Royal Rumble, Ted DiBiase would bring back in the "Underfaker" and try to convince everyone that he was the one and only Phenom. Obviously he wasn't and The Undertaker spent the next several months feuding with The Million Dollar Corporation. IRS would hijack (reprocess) the Urn and everyone's favorite walking condominium, King Kong Bundy, would ambush The Deadman at the Royal Rumble in 1995.
The two would come to blows at WrestleMania XI (aka, the worst 'Mania of all time). During the match, Paul Bearer would take the urn back only to have Kama steal it and melt it down to wear as a chain. Thankfully, this was obligatory stuff that happened to The Undertaker at WrestleMania and The Phenom dealt an "L" to his third legend in four years. Also, this was one of the first instances of The Undertaker showing his raw power, as he delivered an earth shattering power slam to vanquish the big guy.
15 The Big Boss Man (WrestleMania XV: 8-0)
The best big man in the game versus another one of the best big men in the business, who was in the midst of a career resurgence, inside the confines of Hell in a Cell should have went much better than it did. As the entire company got more realistic and got some attitude, The Phenom went darker and more character driven. Tajer believed he was an unholy, undead cult leading creature of the night and would front The Ministry of Darkness. The first time ever Satan's Structure was erected at WrestleMania had the highest of hopes for the fans. Not even a year earlier was the epic Mick Foley performance in this match. Could The Phenom and the Boss Man come close to that level of greatness? The Undertaker was at his most vile in this match, if you could believe that, and had his unholy trio, The Brood come out and "hang" the Boss Man from the top of the Cell. Tasteless ending, leaving this match low on the list.
14 Mark Henry (WrestleMania 22: 14-0)
After Randy Orton made an issue of it a year earlier, The Streak became kind of like another title. The first contender was The World's Strongest Man, Mark Henry. Their battle would be the first time in WrestleMania history where a Casket Match was held. Nine years after The Demon of Death Valley won the WWE Championship in the same city, at the same event, he would return to the Windy City with a 13-0 record at the show of shows. The two behemoths had been duelling over a shot at then-champion, Kurt Angle, and it led to this match. Henry had spent several years at this point rebuilding himself as a malicious, nasty, heel and, of course, The Deadman at 'Mania is a sight to behold. Despite the match being so-so, the veteran hand Henry finally got a marquee spot as The Undertaker helped send Henry higher up the card. As for The Phenom, Henry was yet another big man that 'Taker made a lot better than he was.
13 Diesel (WrestleMania XII: 5-0)
Of all the humongous souls The Reaper of Wayward Souls reaped, Big Daddy Cool Diesel's was certainly the best of the big men. Also notable was the fact that at WrestleMania XII, Diesel became the first member of the legendary and controversial Kliq to become a tally mark on The Undertaker's WrestleMania win card. Their program was a damn good one too. What started as a battle over who should be the #1 Contender became a battle of wits as both men would try to one up each other in their mind games. As slick as Kevin Nash was though, he was no match for The Phenom and even though The Undertaker revealed Diesel's visage inside a coffin, Diesel took The Phenom to his limits. Diesel tested 'Taker in a way that fans had yet to see. Despite winning, the sight of seeing 'Taker get beat up actually prepared us all for what would happen the next night on Raw when Mankind debuted. This is when we began to see a more vulnerable Deadman.
12 Jimmy "Superfly" Snuka (WrestleMania VII: 1-0)
All streaks have to start somewhere and for The Deadman's walk through his WrestleMania graveyard, the journey began with "Superfly" Jimmy Snuka. The match was not met with a lot of fanfare and not promoted too heavily, but The Undertaker and Paul Bearer would get to measure Regis Philbin for a casket during their pre-match interview. This might have been the only Deadman match in WrestleMania history to not be treated as at least the undercard main event. The legend of The Undertaker would continue to grow here as the great announce team of Gorilla Monsoon and Bobby Heenan put over just how evil the big guy was and how handedly he decimated a legend like The Superfly. He was already on a tear when the showdown with Snuka came, but afterwards the general thought became a reality - The Undertaker was unstoppable.
11 Sycho Sid (WrestleMania 13: 6-0)
In early 1997, Shawn Michaels had lost his smile, Bret Hart was warring with an up-and-coming Rattlesnake, and the nWo were crushing it on the other channel. Despite never needing a title, Vince McMahon was left with no choice but to put the strap on his most trusted soldier. At WrestleMania 13, The Undertaker would ascend to the mountain top for the second time in his career, defeating Sycho Sid at the Rosemont Horizon in Illinois. When Michaels "retired," the supposed rematch to the Iron Match from a year prior with Bret got tanked and the deck needed to be reshuffled. HBK sat out of 'Mania and a month prior Austin, Vader, 'Taker, and Hart had a Royal Rumble flavoured Fatal 4-Way to determine who would be champion. A little more reshuffling of the deck would place the strap in Sid's hands and see The Deadman as his challenger. While not completely entrenched in The Attitude Era yet, The Deadman's victory at WrestleMania signaled the old guard was gone and a new era was here. A very different kind of champion was leading the company into the "Dark Days of The Deadman."
10 Batista (WrestleMania 23: 15-0)
The Phenom's latter two WrestleMania title victories were both foregone conclusions to the mythical rise of The Streak, so the matches themselves both had to be hyped very well to steal the show. Even if you knew The Demon was going to walk out with the strap, you had to believe that there might have been chance that simply wasn't going to happen and that The Streak would be broken. The Undertaker vs. World Heavyweight Champion Batista at the 23rd annual Showcase of the Immortals sought to best the night's main event instead of Shawn Michaels against John Cena. What was considered to be a throwaway match for the SmackDown main event in Detroit lit a fire under both men and the match itself wound up being one of the best in both of their WrestleMania careers. It was certainly The Animal's best showing. The match proved that The Phenom was not slowing down one damn bit and was somehow getting better with age.
9 Edge (WrestleMania XXIV: 16-0)
One year after defeating Batista, The Undertaker was again the #1 Contender to the World Heavyweight Championship and this time he was gunning for Edge in the Blue Brand's main event in Orlando. Edge had been consistently building his own legacy as well, as the tag team specialist had emerged as The Rated-R Superstar, taking all of the real life heat he had to became the top heel in the business. With both men being at the top of their games, there was no better way to close WrestleMania out and the main event was set. With Edge on as much fire as he was, there was a legit belief that The Streak would end at 15. But with The Citrus Bowl engulfed in the fires of The Deadman's stalk to the ring, that scintillating feeling grew, as all of the mind games were at an end. It became apparent, no matter how good Edge (or anyone else) was at WrestleMania, The Undertaker brings it up to level 11 to vanquish his opponents. For the second year in a row, The Phenom was the true showstopper at The Show of Shows and would close the night as the new World Heavyweight Champion.
8 CM Punk (WrestleMania 29: 21-0)
Five years prior to WrestleMania XXIX, even in defeating them, The Undertaker was taking on young lions and crafty vets who weren't given the chance to shine. So even though he might have complained that he wasn't in the WrestleMania main event, CM Punk was still booked in a big way at the 29th annual event, in a spot against The Undertaker. But not just any spot - with Paul Bearer's recent passing, Punk and Paul Heyman played that angle up full tilt to get under the skin of The Deadman, hoping he'd make a big mistake and that CM Punk would cement his own legacy and become the one in 20-1. After going 20-0 at 'Mania, the fans did start to begin questioning just how much gas was left in The Phenom's tank and how many more times he could eke out a win at The Grandaddy of Them All. Even during the era where Punk was over anywhere and everywhere, when faced with the the task of taking on The Undertaker, he was still a small fish in a big pond and again The Deadman worked the match of the night as he shut the mouth that roared.
7 Kane (WrestleMania XIV: 7-0/XX: 12-0)
When The Undertaker works against his evil younger brother Kane, you know you're going to get a supernatural build-up to the event, and luckily The Brothers of Destruction's two WrestleMania encounters were separated by several years. This allowed for vastly different stories to be told each time. Their first encounter at XIV showed how vulnerable The Phenom could actually be, as he originally declined to fight his brother. But after weeks of being destroyed by his brother and not fighting back, he was left with choice but to teach his younger brother the harsh lesson that as dark and evil as The Devil's Favorite Demon can be, The Demon of Death Valley is that much darker. That much more sadistic. And at WrestleMania XIV, Kane simply had no shot.
Several years later, having helped Mr. McMahon bury his brother alive late at Survivor Series 2003, we have The Big Red Machine to thank for Deadman, Inc. closing its doors, as The American Bad Ass biker gimmick was literally buried and The Undertaker returned as The Deadman at the WWE's home arena, Madison Square Garden for WrestleMania XX.
6 Jake "The Snake" Roberts (WrestleMania VIII: 2-0)
The Deadman's first year was one of the most successful runs anyone could have. He was undefeated and became at the time, the youngest WWE Champion ever. More importantly, evil found a friend in the sinister Jake "The Snake" Roberts and the devilish duo appeared as uninvited guests at the Macho Man's wedding reception. But just when Jake and Randy's war was about to take a turn for the absolute worst, with Roberts about to decapitate Miss Elizabeth with a steel chair, Mr. and Mrs. Macho had the unlikeliest of saviors in The Reaper of Wayward Souls. Jake would try to play mind games with the master and lose miserably. He asked The Undertaker whose side he was on ("not yours"), he would lock 'Taker's hand in a coffin, and level him with chair shots. But you can't kill The Deadman and at WrestleMania VIII, The Phenom's face turn was cemented. The match was over 20 years ago now and there is still narrowly a fan who doesn't cheer for The Undertaker, even if he is supposed to be the villain.
5 Ric Flair (WrestleMania X8: 10-0)
As we enter the top five, we see the first time since WrestleMania VII where The Undertaker was a true heel heading into WrestleMania. That year, 'Taker would face off against the beloved Nature Boy in Ric Flair's first Show of Shows since he walked in as WWE Champion ten years earlier. While it might have seemed slightly unbelievable that The Undertaker in his prime would have any trouble defeating Ric Flair, the match was set to be a No Disqualification brawl in order to even the odds. This war and the hype leading up to it showed a much different side of The Phenom. While he began his run many years before as a heel, he was a heel by design, just an undead creature from beyond the grave.
This time 'Taker showcase a more human side to his heel persona with personal attacks. After Flair cost The Undertaker his match at No Way Out a month earlier, Big Evil wanted a piece of The Dirtiest Player in the Game. Flair, a principal owner of the WWE at that time, would refuse the challenge. So Taker did what any bully would do, destroy the man’s best friend, Arn Anderson, and oldest son to get Flair to sign on the dotted line. The match itself was one of the few instances during Flair’s latter years that he looked like The Nature Boy of his younger days.
4 Randy Orton (WrestleMania 21: 13-0)
This is it, Creatures of the Night. The very moment where The Streak became The Streak. Before clashing with Randy Orton at WrestleMania 21, the fact that The Undertaker was undefeated at WrestleMania was mentioned in passing as a sports statistic. But The Legend Killer had not only targeted the legacy of The Undertaker, but he was determined to destroy the legacy of The Streak as well. Since there was seldom a big deal made about it back then, there actually was a palpable feeling that Orton might actually defeat The Deadman at WrestleMania. After all, he went over just about every other legend he faced and now he enlisted the help of his Hall of Fame Daddy and his perpetually broken arm. While putting forth a strong and serious effort, young Mr. Orton would learn what 12 other men and the WWE Universe had already known: at WrestleMania, there is not stopping The Deadman…unless your name is…
3 Brock Lesnar (WrestleMania XXX: 21-1)
Thirty years of moments - Hulk Hogan slamming Andre the Giant, HBK ziplining to the ring, Motörhead playing out The Game, Rock-Austin; all of these moments pale in comparison to the sound of 70,000-plus stunned and shocked into silence. Before WrestleMania XXX, The Undertaker actually had never beaten The Beast Incarnate. Even though the build was lackluster, even though Brock had actually lost a little heat, and even though it seemed academic that The Undertaker was going to win, The Deadman's legacy was forever altered when he decided to come to New Orleans to face The Beast. Even the match itself was standard fare from these two monsters laying their stuff in. It had been over ten years since we'd seen these two destroy each other, so it made the match exciting. It was exciting as they told a compelling story, even though we all knew The Phenom would find a way to finally fell The Beast. Until he didn't win - The Streak was over. The immortal Undertaker was humbled and made human in one of wrestling's most compelling moments ever.
2 Triple H (WrestleMania X-Seven: 9-0/XXVII: 19-0/ XXVIII: 20-0)
It would make sense that the two longest tenured WWE in-ring performers would have a trilogy of matches at WrestleMania. Despite their amazing back-to-back wars at XXVII and XXVIII, The American Bad Ass and The Cerebral Assassin's first encounter at WrestleMania X-Seven (aka the greatest 'Mania ever) might be their best, simply because the two top stars were tossed together as if they were an afterthought. That is the amount of star power the WWE had when they rolled into The Astrodome. Some afterthought. The future Hall of Famers had one of the best matches on the card.
The veterans' ability to tell a story again came back several years later in the second and third part of an epic WrestleMania-spanning saga. On the 02-21-2011 episode of Raw, the pair simply stared at each other and then the 'Mania sign to set the stage for WrestleMania XXVII, where Triple H would deliver a beating to The Phenom, the likes of which had never been seen before. For the first time in the history of his career, The Deadman was carted out of the ring on a stretcher. Even in victory, 'Taker practically begged Triple H for a rematch and Triple H finally acquiesced, this time in Hell in a Cell, which would be dubbed the End of an Era and viewed as the truest end of The Attitude Era.
1 Shawn Michaels (WrestleMania XXV: 17-0/XXVI: 18-0)
Similar to watching a Deadman at WrestleMania match where victory is imminent (unless facing Brock), Shawn Michaels was the inevitable number one choice here. Their battles were already epic long before their WrestleMania saga started. Their inaugural Hell in a Cell over a decade earlier. The Casket Match that spelled the end of HBK's career for a while. Being the last two participants and then the first two in the ring at back-to-back Royal Rumbles. There was only one way to celebrate the 25th anniversary of The Showcase of Immortals, with a clash of the WWE's most stalwart loyal soldiers from long before The Attitude Era and beyond it. Seldom does every single person feel electricity surrounding a match. Even less than seldom does the match deliver on all of the promise of glory. Mr. WrestleMania against The Streak was poetry, art, and wrestling in its best form, and if you don't think so, then you just don't understand how wrestling works.
Naturally with a match that great, there was no way to top it, except if there was something on the line besides pride. One year later, HBK put his career against The Streak and while the match was only a fraction below a year earlier, the match was HBK's swan song and. so far. he is seemingly one of the only Superstars to stay retired.