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 18. Giant Gonzalez (WrestleMania IX: 3-0)
17 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.
16 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.
15 15. The Big Boss Man (WrestleMania XV: 8-0)
14 14. Mark Henry (WrestleMania 22: 14-0)
13 13. Diesel (WrestleMania XII: 5-0)
12 12. Jimmy "Superfly" Snuka (WrestleMania VII: 1-0)
11 11. Sycho Sid (WrestleMania 13: 6-0)
10 10. Batista (WrestleMania 23: 15-0)
9 9. Edge (WrestleMania XXIV: 16-0)
8 8. CM Punk (WrestleMania 29: 21-0)
7 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.
6 6. Jake "The Snake" Roberts (WrestleMania VIII: 2-0)
5 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.
4 4. Randy Orton (WrestleMania 21: 13-0)
3 3. Brock Lesnar (WrestleMania XXX: 21-1)
2 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.
1 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.
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