Revisited Rivalries: The Undertaker vs Randy Orton

Two legends of the WWE ring only crossed each other once, but their feud would be a captivating yearlong feud that spanned some of WWE's biggest shows and created some of that year's most significant moments. It is a tale of a young, cocky, arrogant superstar named Randy Orton against the already legendary Undertaker. Their rivalry would span over the whole of 2005, involving Bob Orton Jr, caskets and finishing off their feud and year with a memorable match inside Hell in a Cell. The yearlong rivalry continues to be highly regarded as The Undertaker helped elevate a rising Randy Orton into superstardom.

In May 2002, 22-year-old Randy Orton received the opportunity of a lifetime on SmackDown when he faced The Undertaker for the Undisputed Championship.

This was the very first time the two ever squared off.

Throughout the match, Taker would take a hip toss, huge backdrop and clothesline over the top rope. It was a testament to how giving he would be to younger talent.

When returning to Gorilla, Vince was upset with Undertaker for being far too generous.

Taker’s retort was, “Aren’t we trying to get guys over?

Randy Orton elaborated on this backstage moment:

“The position I was in that night, to work with him, [the main thing I thought] was how lucky and blessed I was, And for whatever reason, he saw something in me. So ‘Taker said something along the lines of ‘Vince, full circle man, that’s what we do. Isn’t that what we’re trying to do here? Get guys over? Like ‘that’s the position I’m in’ kind of thing. And I just remember sitting back there. I wasn’t a part of the conversation but a fly on the wall. I just remember thinking, ‘Wow, OK’

Wrestlemania XXI

Fast forward three years, Randy Orton had become the youngest world champion and was now the self-proclaimed Legend Killer.

Bruce Prichard approached Randy to share the news that The Undertaker requested to work with him at WrestleMania.

With his confidence and arrogance at an all-time high, Randy challenged The Undertaker to a match at Wrestlemania in a 'Legend vs Legend Killer' contest.

A slap to the face was all it took for Randy to earn Taker’s full attention.

A contract signing took place between the two where Randy Orton warned The Undertaker that he had just signed a contract that would turn his undefeated streak into nothing more than a myth as Orton would turn it from 12-0 to 12-1.

In the episode of Smackdown before Wrestlemania, Bob Orton Jr approached the Undertaker and asked him to take it easy on his son. But in reality, it was all a setup as Randy Orton used his father’s distraction to deliver an RKO to show The Undertaker that he could hit the move whenever he was ready in Los Angeles at the biggest show of the year. 

At Wrestlemania 21, The Undertaker defeated Randy Orton but not before a close call between the two that hooked the crowd. It appeared as though Randy Orton had the match won at one point as he delivered an RKO, but The Undertaker kicked out at the very last second. Bob Orton Jr also appeared and interfered, hitting Taker with his cast. The ending came when Orton tried to deliver a Tombstone of his own, only for The Undertaker to reverse it and hit his trademark Tombstone for the victory.

The Streak remained intact.

While The Undertaker noted that Randy stepped up and delivered years later, the rehearsal told a different story.
Randy Orton elaborated on this during an episode of WWE Untold:

“This is my second WrestleMania, I’m 24, I’m being given the world. My f***ing dad is there, ‘Taker is there. But I get down there just as they’re finishing up. I worked with the Undertaker for nearly a year, and it all started with me missing rehearsal for the biggest match of the year,”

The Rematches

A rematch between the two occurred at Summerslam; this time, Bob Orton's interference worked. Disguised as a fan, he ambushed the ring, distracting Taker, which allowed Randy Orton to deliver an RKO and the pinfall.

As Orton celebrated with the fan, he revealed that the fan was his father, Bob Orton Jr.

Also, during the episode of WWE 24, Randy Orton joked that the reveal was nothing like Eric Bischoff’s since Bob’s makeup was so poorly executed.

A second rematch was booked between the two that took transpired on Smackdown. During the match, Bob Orton drove a truck with a casket attached to the back to ringside. The Undertaker, after the distraction, still managed to gain control and decided to put Randy Orton inside the casket. But when he opened it, he saw a mannequin of himself. The Undertaker, in a rare moment, spooked, still managed to pick up the win with a tombstone despite the craziness of the life-like mannequin of himself in the casket.

A week later, as Randy Orton and his father were in the ring, druids brought down a casket, and the Undertaker appeared on the screen. He told them to look inside the casket. Inside we see mannequins of both father and son. Undertaker told both that this would be their fate at No Mercy when they square off in a handicap casket match.

At No Mercy on October 9, 2005, The Ortons won the casket match, placing The Undertaker inside after hitting him with a chair. Afterward, they locked The Undertaker inside the casket, rolled it up to the stage, dumped kerosene on it and then set it alight. This was reminiscent of when Kane did the same to The Undertaker after his casket match with Shawn Michaels at the Royal Rumble in 1998.

The Undertaker disappeared for several weeks from WWE television until Survivor Series 2005. Randy Orton won the traditional 5-on-5 Survivor Series match for his Smackdown brand by hitting the RKO on Shawn Michaels.

As the members of the SmackDown roster hoisted Randy Orton onto their shoulders, an all too familiar gong rang.

Druids then brought a casket out onto the stage and propped it up. As the casket caught fire, The Undertaker emerged in his triumphant return.

The Undertaker then entered the ring to clean house as several members of the SmackDown roster were laid out.

Meanwhile, Randy managed to narrowly escape but soon found himself challenged to face The Undertaker in a Hell in a Cell match at Armageddon.

On December 18, 2005, Randy Orton had nowhere to run as he was trapped inside the cell against The Undertaker.

The Undertaker exacted revenge at Armageddon, picking up the victory in their vicious and brutal Hell in a Cell match, which concluded their almost yearlong feud.

With the conclusion of this epic match, the rivalry ended on a high note, telling a compelling story between the two. Before their feud, Randy Orton found himself in limbo after leaving Evolution, and his babyface run became unsuccessful and lost in the shadow of Batista's face turn against Triple H. This feud with the Deadman reignited Randy Orton and placed him back as a top heel on the Smackdown roster, where he would be positioned just a few months later in the World Heavyweight Championship match at Wrestlemania 22.

Just as Randy Orton has noted, if it wasn’t for The Undertaker, none of this would have ever happened.