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.
The Undertaker had an on-again, off-again relationship with his manager Paul Bearer, who turned heel on him at SummerSlam 1996 and spent the next year and a half antagonizing his former protégée. One of the men Bearer recruited to try to take 'Taker down was Vader, starting at the 1997 Royal Rumble. The two would battle it out in the Rumble itself, as well as twice clashing for the WWE Championship under Bearer’s direction. Their best match was at July’s Canadian Stampede, a great little show with a fiery hot crowd that saw Vader come just short of winning the World Title.
14 Bret Hart
The Undertaker’s debut match in the WWE came in a Survivor Series match against a team featuring Bret Hart and Hart was the first man to enter the ring against The Phenom. More relevant to this list, Hart and The Undertaker fought over the WWE Championship on multiple occasions in 1996 and 1997, including headlining SummerSlam ’97. The best match between the two, however, came at In Your House 13: Final Four in a Four Corners Elimination. After Stone Cold Steve Austin cheated to win the ’97 Royal Rumble, a rematch put Austin, Hart, Undertaker, and Vader in an elimination match to determine who would win the vacant WWE Championship. The Undertaker and Hart were the last two men, with Hart escaping from a Tombstone to win the match.
13 John Cena
While we never got the epic John Cena vs. The Undertaker, Streak v. Title match at a WrestleMania, the two did cross path early in Cena’s career with some very solid matches that have been somewhat forgotten. Cena, in his Doctor of Thuganomics persona, declared himself a locker room leader in 2003 after only one year in the WWE. The Undertaker, as the American Bad Ass, did not appreciate this young whippersnapper coming all up in his yard, and decided to express his displeasure via a number of sharp kicks to the head. The two locked up at Vengeance 2003, with 'Taker coming out on top, and had a great main event on SmackDown just before 2004’s Great American Bash. The two had good chemistry and it’s a shame we never saw a rematch during Cena’s time on the top of the card.
12 Randy Orton
Randy Orton’s Legend Killer phase helped build him up to the main-event level star he is today, and it all really started with his attempt to end The Undertaker’s WrestleMania streak in 2005—the first year “The Streak” was really played up as a thing to beat, rather than just an interesting piece of trivia. Their WrestleMania match was solid and the interference of Cowboy Bob Orton led to a Handicap Casket match which saw Orton lighting 'Taker’s casket on fire, but the true highpoint of the feud was the blowoff at Armageddon ’05 in a Hell in a Cell, a bloody, epic affair which saw both Ortons throwing everything they had at 'Taker, only to come up just short.
11 Big Show
The WWE loves their giant-versus-giant matches, though they’re usually a bit plodding and boring for my taste. One of the exceptions was The Undertaker-Big Show feud in 2008, as Show teamed up with SmackDown General Manager Vickie Guerrero to routinely interfere with 'Taker’s matches. While they had matched up before, including a Handicap match as part of the Streak at WrestleMania XIX, their No Mercy 2008 match was their best, with Show debuting his knockout-punch finisher to leave 'Taker cold in the ring. It’s a pity their feud-ending Casket match wasn’t particularly good.
No one has wrestled 'Taker more than Kane, so the question isn’t why Kane’s on this list, but why he’s not higher. The Undertaker and his kayfabe half-brother have flipped from being rivals to teammates more times than I can count and a fight between The Brothers of Destruction has always been something the WWE has gone back to throughout the years whenever they needed an opponent for The Deadman. Because they’re both unstoppable demonic characters, their matches too-often devolve into a no-selling competition, but the individual moments of their rivalry are among the top in WWE history, from Kane ripping the door off of the Hell in a Cell in his debut to Kane setting Undertaker’s casket on fire to Kane killing off the American Bad Ass and leading to the return of The Deadman. So what if their matches are often underwhelming—as far as storyline goes, it’s hard to top these two. If you want to watch one match in particular, go back to Unforgiven ’98 and the first ever Inferno match, an “only in the Attitude Era” sort of invention.
9 The Rock
The Undertaker and The Rock didn’t cross paths as much as you might expect from two of the biggest stars in the company’s history; the dramatic difference in their characters might have something to do with that. Twice, though—in the back half of 2000 and in early 2002—the two had extended conflicts over the WWE Championship. Their best match against one another came as part of a Triple Threat with Kurt Angle at Vengeance 2002, as the three interfered and attacked one another leading up to the Pay-Per-View and then turned in a well-booked, well-balanced match which saw The People’s Champion come out on top after a thrilling series of finishers at the end.
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.
Batista and The Undertaker engaged in a hot feud in 2007, with 'Taker winning his first World Heavyweight Championship from The Animal at WrestleMania 23. Something about their in-ring styles clicked perfectly, with the two going on to great Steel Cage, Last Man Standing and, yes, Hell in a Cell encounters over the course of the year. No one in history has had as many great matches with 'Taker in succession, and their physical and brutal slugfests throughout the year was the single best feud of 2007. It had to make the list, even if it didn’t last as long throughout 'Taker’s career as some of the other top names.
6 Brock Lesnar
The man who ran out for the DQ in that 'Taker-Angle match? One Brock Lesnar. The Undertaker and Lesnar have had two notable feuds. The first came in 2002, with the two feuding over Lesnar’s WWE Championship, culminating in a gory, bloody Hell in a Cell match at No Mercy, reverting the bout into a vicious and violent match, rather than the goofy “escape the cage and climb” parody of itself it was threatening to turn into. But that’s all a footnote to their more recent encounters, which saw Lesnar pull off the most shocking moment in WrestleMania history, ending the Streak at WrestleMania XXX.
Speaking of stuntfest Hell in a Cells, The Undertaker-Mankind match from King of the Ring ’98 is still the gold standard, with the image of the hell Mick Foley put his battered body through for the sake of the match being one of the most enduring of The Attitude Era. The feud between Mankind and 'Taker was more than just one match, though. Mankind’s debut in the WWE saw him interfering and costing 'Taker several matches, and included a long-term arrangement with Paul Bearer as his manager, fighting in Buried Alive matches and Boiler Room Brawls. The two never really had a bad singles match in their careers, but the Hell in a Cell will overshadow everything else they have done.
4 Shawn Michaels
The Heartbreak Kid and The Deadman have provided some of the most iconic matches in wrestling. WrestleMania XXV and XXVI saw two of the greatest matches in WWE’s history, with two legends going at it in their mid-40s and leaving it all on the table, including the classic Streak vs. Career match which saw Shawn Michaels ending his time as an active wrestler. For my money, though, their feud in 1997 was even better—a feud which started when Michaels accidentally clocked 'Taker with a chair at SummerSlam, leading to the first Hell in a Cell match in history at Badd Blood in October. That’s the match that saw the debut of Kane, as well—it’s probably the most significant match in Undertaker’s long career. Had the two crossed paths more often—they only appeared in 14 televised matches against one another, with only six on Pay-Per-View—HBK would be higher on the list.
There are many who believe that 'Taker’s 2008 feud with Edge was the best of his career and it’s hard to argue too strenuously against it. The feud started when Edge cashed in his Money in the Bank briefcase on SmackDown, and then later heated up when he interfered in a Hell in a Cell match with 'Taker and Batsista, disguised as a cameraman. The two clashed in five great singles matches in mid-2008, with the culmination being yet another classic Hell in a Cell match at SummerSlam, which turned into a sort of hybrid-HIAC-TLC match towards the end as Edge found gratuitous plunder underneath the ring, before being chokeslammed through the canvas into fire. Loads of fun. And let's not forget that 'Taker and Edge closed out WrestleMania XXIV in a classic main event encounter.
2 Triple H
Three times, Triple H and The Undertaker have matched up at WrestleMania. Their WrestleMania X-Seven clash, setup by Triple H claiming he had beaten everyone else in the WWE, was good in its own rights, but their rematches at WrestleManias XXVII and XXVIII, in No Holds Barred and (yet another) Hell in a Cell match were legitimately great, if a bit overbooked at times. More than anything, though, it’s just the fact that 'Taker and Triple H have been thorns in each other’s sides for more than a decade and a half, off and on—whether it’s The Rock introducing the American Bad Ass gimmick to help him fight off the McMahon-Helmsley Regime in early 2000, or teaming with Kane against Triple and Stone Cold Steve Austin, or Triple H desperately trying to end 'Taker’s streak to get revenge for the end of Shawn Michaels’ career, the two always seemed to click on the biggest stage.
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.