For nearly 25 years, The Undertaker has earned unmatched respect from both the WWE Universe and his peers by facing off with the very best the squared circle has had to offer. Nearly every competitor who has left a mark on sports-entertainment in the past quarter century has found themselves in the intimidating presence of the legendary Phenom at least once. But which of The Deadman’s opponents proved themselves to be the most worthy adversaries?

Watch videos of The Phenom's unforgettable returns to the ring

As The Undertaker prepares to avenge The Streak against Brock Lesnar at SummerSlam, WWE.com looked back at The Deadman’s 15 toughest opponents. These are the men that danced with the devil and lived to tell the tale.

Diesel

Following his loss to Bret “Hit Man” Hart for the WWE Championship at Survivor Series 1995, Diesel set his sights on The Undertaker. After Big Daddy Cool cost The Deadman the WWE Title at Royal Rumble 1996, The Phenom sought retribution at WWE In Your House 6: Rage in the Cage. As Diesel challenged Hart for the WWE Title in a Steel Cage Match, The Undertaker tore open the ring canvas and pulled Big Daddy Cool down to hell in a visual that shocked the WWE Universe.

The actions of both Superstars would lead to a colossal showdown at WrestleMania XII. With the tale of the tape rather even, there was a very real threat that The Deadman’s WrestleMania Streak would have ended in its infancy. Nevertheless, the virtual stalemate ended when  The Undertaker lifted Big Daddy Cool up and delivered a Tombstone to secure the win, effectively ending the rivalry. — KEVIN POWERS

Jake "The Snake" Roberts

One of The Undertaker’s earliest allies was Jake “The Snake” Roberts, who had gotten back in touch with his evil side in summer 1991. The terrible twosome struck fear into the heart of the WWE Universe when they crashed the wedding reception of “Macho Man” Randy Savage and Miss Elizabeth, unleashing a venomous cobra on the bride and groom before viciously attacking Savage.

We found out, however, that The Deadman had some semblance of a soul when he prevented “The Snake” from decking Miss Elizabeth with a steel chair. The Phenom made it clear that he wouldn’t stand for such a thing on Paul Bearer’s “Funeral Parlor,” which led to Roberts slamming a casket lid shut on Undertaker’s hand and DDT’ing Bearer.

“The Snake” smiled as he slithered away, thinking he had sent a message to The Deadman. What he didn’t count on, though, was The Undertaker’s mystic powers giving him the strength to stand up and give chase, dragging the massive casket behind him.

There was no place to hide at WrestleMania VIII for Roberts. “The Snake” threw everything he had at The Undertaker. Still,  The Phenom stood up after taking two DDTs to put an end to Roberts’ reign of terror, Tombstoning him on the arena floor and pinning him to pick up his second WrestleMania win. — BOBBY MELOK

Big Show

The rivalry between The Undertaker and The World’s Largest Athlete began when Mr. McMahon’s Corporation merged with The Undertaker’s Ministry of Darkness in 1999. Unwelcome in this new group, Big Show battled The Phenom and  chokeslammed him through the ring on the June 7, 1999, setting the tone for a rivalry that would endure for the next decade.

“When you compete against The Undertaker, your stress level automatically rises,” The World’s Largest Athlete told WWE.com. “It pushes you to a level that you don’t normally reach.”

After their initial battle on Raw, the duo formed an uneasy alliance that resulted in two reigns as World Tag Team Champions. But the legendary competitors went on to battle in the first-ever Punjabi Prison Match and on The Grandest Stage of Them All at WrestleMania XIX. Joining forces with A-Train,  the giant was unsuccessful in his bid to end The Deadman’s Streak at WrestleMania. Still, their rivalry brought out the best in the massive competitor.

“He made me want to be a bigger, better giant — a better Superstar,” Big Show explained. “I don’t care what anyone says, he’s the best ever in the ring. Period.” — KEVIN POWERS

Mr. McMahon

The “Attitude Era” has long been defined by the epic rivalry between Mr. McMahon and “Stone Cold” Steve Austin. But while The Texas Rattlesnake certainly caused The Boss a great deal of agita, it was The Undertaker who toyed with Mr. McMahon’s heart and soul.

As The Ministry of Darkness became more and more demonic during the late 1990s, the increasingly evil Undertaker focused his efforts on The Chairman in an attempt to control WWE. While competing in an Inferno Match on Raw, the satanic Deadman arranged for a box to be delivered to Mr. McMahon, who was sitting at the commentary table. Following the contest, the box’s contents were revealed to be a stuffed teddy bear which The Undertaker lit on fire. The symbolic burning fur brought The Boss to his knees and remained a lasting image in WWE lore. During that same period, The Undertaker even kidnapped The Chairman’s daughter Stephanie, and planned to wed her in an “Unholy Ceremony.”

The Undertaker maintained a rocky relationship with Mr. McMahon for many years, and  battled his boss in an intense Buried Alive Match at Survivor Series 2003. — ZACH LINDER

Yokozuna

The sight of The Undertaker’s lifeless body rising up from a casket and disappearing into the rafters of the Providence Civic Center at the 1994 Royal Rumble has long haunted those WWE fans who thought they’d seen the last of The Deadman. That night, the massive Yokozuna — assisted by a cadre of villains, including Crush and The Great Kabuki — smashed The Phenom’s mysterious urn, locked him in a coffin and, seemingly, sent him out of WWE for good.

Of course, The Undertaker doesn’t stay down for long. First returning to WWE to vanquish The “Million Dollar Man” Ted DiBiase’s ersatz Undertaker, The Deadman then went looking for retribution against the 600-pound sumo wrestler that put him out of action. At Survivor Series 1994, The Undertaker and Yokozuna met in a return Casket Match with professional throat puncher Chuck Norris serving as the bout’s special guest enforcer. This time, Yokozuna’s backup was neutralized as “Walker, Texas Ranger” karate kicked Jeff Jarrett back to Tennessee, allowing The Deadman to stuff his oversized rival in a specially made casket — double wide and double deep. — RYAN MURPHY

Batista

Winning the 2007 Royal Rumble Match presented The Undertaker with an opportunity to challenge then-champion Batista for the World Heavyweight Title at WrestleMania 23. At The Show of Shows, The Phenom defeated The Animal to win the title, but the animosity between the two Superstars was far from over. Following their epic clash, Batista and The Phenom engaged in one of the most physical rivalries of the decade.

The hostility between both Superstars wasn’t only intense, it was evenly matched. Their battles after WrestleMania —  a Last Man Standing Match at Backlash followed by a Steel Cage Match on SmackDown — both ended in a draw. Edge cashed in his Money in the Bank contract following the match on SmackDown, putting the rivalry between The Animal and The Deadman on hold.

But the duo reignited their mutual enmity at Cyber Sunday 2007 with The Undertaker now challenging for Batista’s World Heavyweight Title. The Animal retained the championship at Cyber Sunday and again inside Hell in a Cell at Survivor Series following an assist from Edge. Their final clash came at WWE TLC 2009 with The Phenom successfully defending his championship against The Animal in a brutal Chairs Match. — KEVIN POWERS

The Million Dollar Corporation

Maybe “The Million Dollar Man” Ted DiBiase was jealous of The Undertaker. For all his piles of cash, DiBiase never enjoyed the championship success or adulation from the WWE fans that came so naturally for The Deadman. Perhaps that is why DiBiase brought in an Undertaker of his own in 1994. The legit Phenom had been absent from WWE for most of the year, but returned at SummerSlam to oust the imposter.

But “The Million Dollar Man” wasn’t done. He formed a Million Dollar Corporation of the ring’s top thugs. Throughout 1995, The Deadman fended off DiBiase’s officers of chaos including Irwin R. Schyster at the Royal Rumble, the massive  King Kong Bundy at WrestleMania XI and an intense competitor called Kama who was known as “The Supreme Fighting Machine.” The shoot-fighting newcomer melted The Undertaker’s urn down to a chunky necklace, but was stuffed inside a casket at SummerSlam to bury DiBiase’s Corporation for good. — ZACH LINDER

Edge

It didn’t have to be The Undertaker. He was just in the wrong place at the wrong time. Following a brutal Steel Cage Match where The Deadman successfully defended the World Heavyweight Championship, Edge cashed in his Money in the Bank contract to win the title, setting off a chain of events that jumpstarted a year-and-a-half-long rivalry.

Forced to battle his way through the SmackDown roster thanks to Vickie Guerrero, The Undertaker finally earned a singles contest against Edge at WrestleMania XXIV where The Phenom defeated The Rated-R Superstar to win the title. The new champion successfully defended it at Backlash via submission with Hell’s Gate, but Vickie banned the hold and stripped The Undertaker of the championship. Neither Edge nor The Undertaker was able to regain the title at Judgment Day, and a Tables, Ladders & Chairs Match was scheduled for One Night Stand.  Edge defeated his rival, and The Undertaker was banished from WWE due to the bout’s stipulations.

But in the end, Edge was his own worst enemy. He had married Vickie Guerrero in an attempt to wield power on SmackDown, but when their relationship began to take a turn for divorce court, Vickie reinstated The Undertaker. The Rated-R Superstar was brutalized in a Hell in a Cell Match at SummerSlam and The Undertaker chokeslammed his rival off a ladder and through the ring. He was just in the wrong place at the wrong time. — ZACH LINDER

Randy Orton

Prior to Brock Lesnar at WrestleMania 30, The Undertaker's legendary undefeated streak was never in more jeopardy than during Randy Orton’s clash with The Deadman at WrestleMania 21. The 24-year-old Orton, looking to make a name for himself, intended to be the first man to defeat The Undertaker at WrestleMania. And for a while, he made WWE fans believe it.

The Phenom did defeat the cocky upstart on The Grandest Stage of Them All, but Orton insisted he could beat The Deadman, whether it was at WrestleMania or elsewhere. At SummerSlam, The Legend Killer’s prophecy came true when Orton defeated The Undertaker with help from his father, WWE Hall of Famer “Cowboy” Bob Orton. The mind games continued on SmackDown throughout 2005 and the two Ortons defeated The Deadman once again in a Handicap Casket Match at No Mercy. Following the bout,  they doused the casket with gasoline, lit it ablaze and The Undertaker disappeared for weeks.

When The Phenom returned, it was revealed that only one match could conclude his long rivalry with Orton: Hell in a Cell.  The Undertaker finally pinned the brash rival at Armageddon to settle their bitter score for good. — ZACH LINDER

Triple H

Few rivalries have produced more epic matches than the war between The Undertaker and Triple H.

At WrestleMania X-Seven in 2001, the two legends brawled all over Houston’s Astrodome, leaving a path of destruction in their wake. No place in the arena was safe, as they battled around (and went through) the Spanish announce table, took over the production area and used anything within reach to clobber each other. The Deadman withstood chairshots and a blows from Triple H’s trademark sledgehammer to extend his Streak to 9-0.

It would be 10 years before the two met again at WrestleMania, this time in a No Holds Barred Match. After a half-hour of all-out combat, Triple H begged The Phenom to stay down after three Pedigrees and a Tombstone, but Undertaker refused, trapping The Game in Hell’s Gate for a submission victory, his 19th. But Triple H accomplished something no other Superstar had, leaving The Deadman so battered he couldn’t leave WrestleMania on his own feet.

In what was billed as “The End of an Era,” they met for the final time inside the brutal structure known as Hell in a Cell. Once again, The Deadman weathered the storm of offense from The Game, who had a helping hand in guest referee Shawn Michaels. Nearly 80,000 people in Sun Life Stadium watched in awe as The Undertaker pinned Triple H after two devastating Tombstones, extending his unbelievable Streak to 20-0. — BOBBY MELOK

"Stone Cold" Steve Austin

When “Stone Cold” Steve Austin challenged The Undertaker for the WWE Championship at In Your House: A Cold Day in Hell, few could have predicted the intense animosity that these two cornerstones of WWE would one day have for each other.

Throughout 1998, The Texas Rattlesnake rose to championship glory while The Deadman fended off his demonic brother Kane. Once the revered veteran realized his spot as top dog had been threatened, he challenged Austin in an epic battle inside Madison Square Garden at SummerSlam. When The Undertaker came up short, a dizzying tug of war for the title took place between Austin, The Undertaker and Kane.

The Phenom’s inability to become champion led to the formation of The Ministry of Darkness. The newly demonic  Undertaker battled Austin in a Buried Alive Match and, in an infamous moment, “sacrificed” the beer-drinking hero in a macabre ceremony. In spring 1999, The Deadman briefly won the WWE Championship from Austin, momentarily giving The Corporate Ministry an unfathomable amount of power. — ZACH LINDER

Mankind

Before Mankind emerged in WWE in spring 1996, The Undertaker was able to deliver a level of punishment that could stop any foe. But this demented new Superstar presented a new challenge — pain made Mankind stronger.

After defeating The Undertaker in a singles contest at King of the Ring,  Mankind met The Deadman again in the first-ever Boiler Room Brawl at SummerSlam. Paul Bearer shockingly turned on his longtime ally to join forces with Mrs. Foley’s Baby Boy, but that seemed to instill new life in The Phenom. He finally  defeated Mankind in the first-ever Buried Alive Match and again at Survivor Series in a bout where Bearer dangled above the ring in a cage.

Their 1996 rivalry expanded the horizons of brutality, but it was their infamous Hell in a Cell encounter two years later at King of the Ring 1998 that defined each man’s legacy. In one of the most iconic moments in WWE history,  The Phenom tossed Mankind from the top of the Cell and, later, through the cage’s ceiling. Each time, Mankind came back for more, leaving The Deadman incredulous as to how one individual can thrive on so much pain. — ZACH LINDER

Brock Lesnar

Sports-entertainment has rarely seen an ascent quite like Brock Lesnar’s. From the moment he debuted in March 2002, Brock put the locker room on notice and only five months later, he was WWE Champion. And of course, a newly christened champion must face The Deadman.

Lesnar’s first encounter with The Undertaker was a title defense at Unforgiven, and the young champion might have made a mistake by making things personal with his opponent in the weeks leading up to the event. The chaotic contest concluded when each man was disqualified, leaving the WWE Universe dissatisfied. But The Undertaker had the last laugh when he brutally tossed Brock through the event’s set.

Fitting for two competitors of equal intensity, their rematch was set for No Mercy in a Hell in a Cell Match. Once again, Lesnar made things personal and smashed his rival’s hand with a propane tank to gain the advantage. The subsequent pay-per-view encounter was a vicious affair and ended with a busted open Lesnar standing tall on the top of the cage.

Brock defeated The Undertaker again at the following year’s No Mercy in a brutal Biker Chain Match, but that wasn’t the final time the two monsters crossed paths. After losing the UFC Heavyweight Championship in October 2010, Lesnar walked by The Deadman, who was seated first row. The two former rivals locked eyes and it seemed the two might come to blows. The Undertaker stood his ground, though, and later claimed there is an unsettled personal matter between the two. The WWE Universe thought that matter was resolved at WrestleMania 30 when The Conquerer infamously broke The Streak to become the one in 21-1. However, with the two now on a direct collision course towards SummerSlam, their rivalry may be at its most explosive, and surely far from dead. — ZACH LINDER

Shawn Michaels

Few Superstars are as recognized in the cultural zeitgeist as the towering Undertaker and Mr. Hall of Fame himself, Shawn Michaels. Both competitors rose to prominence during the envelope-pushing years of the 1990s, but did not often cross paths until after HBK had reached the top of the mountain as WWE Champion.

As special referee in the SummerSlam 1997 main event between The Undertaker and Bret Hart,  Michaels inadvertently nailed The Phenom with a steel chair to cost him the WWE Title. A pay-per-view encounter to settle their issues ended without a conclusive decision and their next meeting —  the first-ever Hell in a Cell Match — ended in controversy. Three months later, Shawn retained his WWE Title in a Casket Match against The Deadman, but suffered a potentially career-ending back injury in the process.

More than 10 years later, Michaels and The Undertaker  reignited their rivalry in spectacular fashion when they competed against each other at consecutive WrestleManias. The two classics are considered two of the finest matches of all time. Before the clashes, The Undertaker had never been able to defeat The Showstopper on pay-per-view. But after WrestleMania XXVI, The Phenom was 18-0 and Shawn’s career had come to an end. — ZACH LINDER

Kane

“We’ve certainly had a mixed history,” Kane told WWE.com when asked about his lifelong animosity with his brother, The Undertaker.

In truth, no rivalry in WWE history has been as enduring as the one that has burned between The Brothers of Destruction. Since The Big Red Monster first appeared in WWE at Badd Blood 1997, Kane and The Deadman have torn each other apart in gory Hell in a Cell Matches, brutal  Buried Alive bouts and even a fiery Inferno Match. But their rivalry dates back long before Kane’s arrival, beginning in the ashes of a funeral home that The Phenom burnt to the ground, leaving The Big Red Monster with physical and emotional scars he would carry with him for the rest of his life.

Like any siblings, the brothers often put their animosity aside. The former World Tag Team Champions dispatched a group of villains at Raw 1,000 and battled The Shield two weeks after WrestleMania 29. Still, their two bouts on The Grandest Stage of Them All —  first at WrestleMania XIV and  again at WrestleMania XX — remain the defining moments of their extensive animosity.

“To this day, the highlight of my career is my match with The Undertaker at WrestleMania XIV,” The Big Red Monster revealed. — KEVIN POWERS