Even after more than two and a half decades in the business, there’s still few things in wrestling that bring the same amount of goosebumps and anticipation as the lights going out, a gong coming over the sounds system, and The Undertaker emerging from the back. Though he’s been reduced to a part-time performer thanks to his age and legendary status, very few things in the WWE can bring up as much of a big-match feel as an Undertaker appearance—when The Deadman comes to the ring, you know something special is about to happen.
He’s been a major main-event player since he first emerged in a WWE ring at Survivor Series 1990. He’s bridged multiple eras; how many people can say they’ve won a World Title from both Hulk Hogan and CM Punk? The man is a wrestling icon, universally considered one of the top wrestlers of all time with undeniably the best, long-lasting, and consistent gimmick in the business.
If there’s anything negative to say about 'Taker’s career, it’s that his gimmick was so over that for years, the WWE was content to match him up with any big schmuck they could find, knowing that the mystique and aura of The Undertaker would carry the feud. Over the years, 'Taker’s had to deal with duplicates of himself, a stalking DDP, and the various charges of Harvey Whippleman. Combine that with a gimmick that required 'Taker to rarely show any signs of weakness or distress, and you have quite a few matches which don’t exactly hold up when removed from the context of their times.
Still, 'Taker’s feuds and rivalries have helped shape the history of the promotion like no one else. Here are 15 of The Undertaker’s greatest opponents—the ones that helped bring originality, classic matches, and goosebump-inducing moments over more than a quarter century of wrestling.
14 Bret Hart
13 John Cena
12 Randy Orton
11 Big Show
9 The Rock
8 Kurt Angle
Speaking of that Triple Threat, Kurt Angle’s goody-two-shoes All-American persona played very well off of 'Taker’s American Bad Ass style early on in Angle’s career—opposites working well for both comedic moments, like when Angle soaked 'Taker’s bike in a milk-induced celebration and in matches where Angle’s Olympic and amateur background clashed with the power and force of 'Taker’s more strike-focused style. They were both featured on SmackDown during its high point of the brand split, and their WWE Championship match on the September 4th, 2003 edition of the show was a classic, with 'Taker refusing to tap out to the Anklelock on four separate occasions before the match ended in a DQ.
6 Brock Lesnar
4 Shawn Michaels
2 Triple H
1 Stone Cold Steve Austin
The biggest star of the Attitude Era engaged in multiple classic matches against The Deadman at the height of WWE’s popularity, as 'Taker teamed up first with Kane and then with Vince McMahon as part of The Corporate Ministry to be a thorn in Austin’s side. While the two Superstars were fighting as early as 1997 and as late as 2002, it was ’98 and ’99 when everything really hit their peak—The Corporate Ministry storyline, and while Vince McMahon revealed as 'Taker’s “Higher Power” may have been confusing, it was great week-by-week television. Their best match was the First Blood fight for the WWE Championship at Fully Loaded ’99, an Attitude-Era overbooked classic. Their entire feud, though, is worth going back and watching.
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