As 2004 turned to 2005, Randy Orton was positioned as the top face of WWE’s Raw brand. He’d defeated Chris Benoit to become the youngest world champion in WWE history, been booted from the Evolution stable, turned face, and started feuding with Triple H in the main event.

And the fans didn’t like it.

While Orton was athletically gifted and a good worker, he wasn’t much of a face character. He’d gotten over as an arrogant heel, but as a face he was largely without any discernible personality and was quickly losing ground as a vanilla star.

So, WWE changed directions. Batista moved into the WrestleMania main event spot that had presumably been earmarked for Orton. Without any other plans lined up, Orton got shifted into a WrestleMania storyline with The Undertaker. Little could anyone have expected, that on-screen rivalry would extend for the rest of the year—a nine-month storyline with ups and downs that would not only shape each of the principal players’ directions for the rest of the year, but rope in a variety of other talents in their orbit, and shape their careers both on and off screen.

Twelve years later, Randy Orton and The Undertaker remain two of WWE’s biggest stars. Each will be featured in prominent matches at WrestleMania 33 and each are the kind of marquee players whom even casual fans can still readily identify. This article looks back at one of the definitive rivalries of each man’s career, and fifteen things you may not have known about it.

15 15. The Rivalry Wasn’t Originally Supposed To Happen

WWE clearly saw Randy Orton as a valuable commodity. They awarded him his first world title win at SummerSlam 2004 in a choice that was likely related to ensuring he’d beat out Brock Lesnar for the mark of youngest world champion in company history, besides capitalizing on how hot Orton was coming off of besting Mick Foley. Orton turned face and got locked into a feud with Triple H in which he lost the title to The Game. All signs suggest that WWE meant to give Orton his next world title win, and his more formal coronation as the man at WrestleMania 21, getting his win and his championship back from his old mentor.

Plans changed when fans cooled on Orton and warmed up to Batista. In the long run, Batista probably would have splintered from Evolution anyway and turned face. WWE read the writing on the wall, though, and gave Batista the big WrestleMania push originally earmarked for Orton. That freed up Orton. The company both still wanted to treat it as a big deal, and surely recognized he was better as a heel at that point in his career. They killed two birds with one stone, sending Orton hunting for The Undertaker’s WrestleMania undefeated streak in a rivalry that would go on for the rest of the calendar year.

14 14. The Undertaker Gave Randy Orton His First Singles Match At WrestleMania

While Orton was one of WWE’s top stars in the spring of 2005, he did not yet have a one-on-one match at WrestleMania to his name. Rather, the year before, he’d been on the right side of a three-on-two handicap match, teaming with Ric Flair and Batista to get the better of Mick Foley and The Rock’s Rock ‘n’ Sock Connection. Orton picked up the pin for his team and so moved got the biggest push of the group coming out of WrestleMania XX. Just the same, he still hadn’t had a proper showcase as an individual at WWE’s biggest show of the year.

The Undertaker, meanwhile, already had 11 WrestleMania wins under his belt at that point, and 10 of them in singles matches. While the pairing might seem like a mismatch from that vantage point, it actually fit Orton’s brash young persona nicely. He had a gimmick as The Legend Killer just months before, and so aiming to end The Deadman’s streak made a lot of sense for his character.

13 13. A Spot In The Rivalry Got Matt Hardy Into Trouble

After Orton had kayfabe injured The Undertaker, The Phenom returned at the end of Survivor Series 2005 to confront Orton. Orton was riding high at the moment, having scored the win for his SmackDown team over a cast of rival performers from the Raw brand. He sat high on the shoulders of his fell Smackdown roster members before The Deadman’s music hit.

When The Undertaker got to the ring, Orton retreated, and The Phenom was left to lay waste a to a number of smaller stars who were still in the ring and who had impeded The Undertaker’s progress on his way to get his hands on Orton. In a display of dominance, The Undertaker battered anyone he could get his hands on—but couldn’t get his hands on Matt Hardy.

Hardy purportedly thought it wouldn’t fit his character to wait around the ring to get nailed, besides wanting to protect his character against taking an unnecessary drubbing. So, he slipped out of the ring unseen rather than take the choke slam that had been earmarked for him. Hardy got in trouble for ducking out of the spot, with management upset at him going into business for himself, besides The Undertaker himself giving the younger star a scolding in the locker room after the show.

12 12. The Rivalry Included One Of The Last Times A Male Performer Intentionally KOed A Female Performer

There was a period during and coming out of the Attitude Era when it wasn’t so uncommon for men and women to physically engage on air in WWE. The company and its audience seemed to relish in the novelty of the taboo—men getting their hands on women who had wronged them or who otherwise seemed to deserve some sort of comeuppance. It’s why Triple H earned a big pop by hitting a Pedigree on Stephanie McMahon at WrestleMania X8, and why few batted an eye at the Dudley Boyz’ early gimmick of powerbombing valets through tables.

Times have changed, though. Nowadays, WWE looks out more carefully for its public image, besides having strict guidelines based on their relationship with Hasbro—their toy manufacturer—that all but ban male-on-female violence.

In The Undertaker-Orton rivalry, business really picked up when Orton RKOed kayfabe love interest Stacy Keibler. The moment demonstrated that Orton was really getting serious about focusing on his WrestleMania match, besides shoring up the heel turn that WWE was hinting at.

WWE has very rarely seen a man intentionally hitting a move like that on a woman since (though interestingly, the next high-profile instance also involved Orton, with him nailing a DDT on Stephanie McMahon four years later).

11 11. The Undertaker Got Bob Orton Fired

Bob Orton had been diagnosed with Hepatitis C early in his life. The disease is a dangerous one, known to cause liver complications, and it can only be transmitted through blood. Accounts vary as to when or to whom Bob disclosed this health issue to in WWE, but regardless he was aware that he had it when he returned to WWE to play his son’s backup against The Undertaker, and The Undertaker was among those individuals in WWE who most certainly did not know one of the men he was working with had Hepatitis.

The matter came to a head when The Deadman battered Bob bloody during a match to end the rivalry at Armageddon 2005. Afterward, The Undertaker learned of the issue and was purportedly livid with his coworkers. Bob’s time on the WWE roster may have more or less expired at that point anyway, but regardless, The Undertaker got his wish when he demanded that the company let Bob go.

10 10. The Rivalry Galvanized The Streak Angle For The Next Decade

Going into WrestleMania 21, The Undertaker was 11-0 at WrestleMania. WWE had acknowledged The Streak, making casual reference to the fact that he’d never lost at the event, and getting into it a bit more at when Triple H challenged The Undertaker at WrestleMania X-Seven. The Streak was still not the stuff of legend at that point, though, and no one had challenged The Undertaker specifically to end the streak. Randy Orton started that trend, when he decided to challenge The Deadman for the explicit purpose of making history by being the first one to defeat him at WrestleMania.

Because Orton was an ascending top star in WWE, and because The Streak was not yet as entrenched as it would become, fans felt there was a real chance he could defeat The Undertaker. Better yet, the two went on to have a very good match with lots of false finishes, establishing the paradigm of guys trying to end The Streak for years to come.

9 9. Since Their WM 21 Match, Orton And 'Taker Are The Only Two to Work Every Single WrestleMania

By WrestleMania 21, The Undertaker was already a well established part of the WWE landscape, and a regularly featured performer at ‘Mania. Just the same, after 14 years on the WWE landscape, you had to assume he had more WrestleManias behind him than ahead of him. Meanwhile, Randy Orton was less proven, and only performing in his second ever Showcase of the Immortals.

So, it might come as a surprise to fans, 12 years later, that these two would have performed in every single WrestleMania since, not to mention that they’re the only two WWE Superstars to have done so. That stat is a testament to each man’s longevity both in remaining physically capable of performing at the highest level, and for their character work remaining compelling to fans for all these years.

8 8. John Laurinaitis Put The Undertaker At Risk

The Undertaker beat Bob Orton bloody more than once in his feud with Randy Orton, and most prominently so in their the Hell in a Cell blow off match at the Armageddon 2005 PPV. The Deadman was unaware that Bob had been diagnosed with Hepatitis C. Accounts vary as to who else might have known about his condition, but reports seem consistent that Bob knew, and so did backstage powerbroker John Laurinaitis.

Laurinaitis contributed to planning the match, became aware of Bob’s diagnosis, and not only didn’t tell The Undertaker, but didn’t redirect the action of the match, still steering the steel cage encounter toward its bloody climax. The Undertaker was livid when he learned about the entire situation after the match. While Laurinaitis wouldn’t necessarily need to worry about heat from most in-ring talents, the wrath of someone with The Undertaker’s credibility could cause problems, even for an executive.

7 7. The Undertaker And Orton Feuded For Nearly A Year Without A Title Ever Being On The Line

When you think about big name, long term pro wrestling rivalries, and particularly so in the last 20 years, you’ll notice a commonality that there is usually a championship at stake for at least part of the rivalry, if not the whole time. The Undertaker vs. Randy Orton is the exception to this rule, which is particularly strange when you consider The Undertaker is a seven-time world champion, and Orton has held world title gold 12 times. Remarkably, the period when the two men were feuding with each other marks one of the longest stretches when both men were active in WWE, and neither was in contention for a title.

One might argue that the absence of a title is what made the rivalry work. The two started to feud based on personal pride and Orton’s pursuit of The Undertaker’s streak. It continued because the issues between the two characters grew progressively more personal and heated.

6 6. Orton Used Kane’s Playbook Against The Undertaker

Pop quiz—tell me which wrestler I’m describing. This guy challenged The Undertaker at WrestleMania, involved his father to make the issue more personal, and ultimately set fire to a casket with The Phenom inside in order to attempt murder, only for The Undertaker to come back and haunt him?

You might have guessed Kane. You might have guessed Randy Orton. In either case, you’d be correct.

While there were, of course, major differences between Randy Orton and Kane, and the way each man challenged The Undertaker the similarities stand out, and particularly so in hindsight. Kane and Orton represent two of The Dead Man’s longest term rivals, and thus it may not come as surprise, but they used startlingly similar game plans in their attempts at besting him. One notable difference; though each rivalry led to a Hell in a Cell Match, Kane actually beat his brother in that environment in their last iteration of the feud, before winning the feud with victory in a Buried Alive Match. Meanwhile, Orton went down in the Cell to at long last lose the war to The Deadman.

5 5. Orton Was One Of Three Main Eventers From His Developmental Class The Undertaker Put Over

The Undertaker invested the better part of a year in working with Orton. While some naysayers suggest that The Deadman ultimately winning the rivalry hurt Orton’s character, I’d argue that so few guys have gone over The Undertaker in the long run that just going toe-to-toe with him for that long helped his credibility.

Orton was not the only star of his generation to feud with The Undertaker, though. The Viper came up through WWE’s developmental system with a class of main event stars that also included Brock Lesnar, Batista, and John Cena. The Undertaker would put over Lesnar in two separate feuds in The Beast Incarnate’s first run with WWE, before putting him over again at WrestleMania XXX to end The Streak, before ultimately losing a feud to him the following year. The Undertaker also had a long rivalry with Batista in which The Animal ultimately shored up his legacy by beating The Deadman in a rough Hell in a Cell performance.

Interestingly, out of that class, John Cena was the only one The Undertaker never did meaningfully put over—beating Cena in a brief, mostly forgotten upper card feud in 2003 but, at least to date never revisiting the issue. It’s ironic, then that Cena nonetheless emerged as the face of WWE for his generation, amongst these other stars.

4 4. The Feud Incorporated Multiple WWE Hall Of Famers

While Randy Orton and The Undertaker are big enough stars to overshadow just about anyone around them, it’s interesting to note that their rivalry also incorporated multiple Hall of Fame stars. Their kayfabe issue got kicked off by none other than Superstar Billy Graham who, in a guest appearance, dared Orton to do what no one had done before, and pointing him in The Undertaker ‘s direction. In the build to their first confrontation, legend Jake “The Snake” Roberts got involved in the proceedings, warning Orton against taking The Phenom too lightly (he took an RKO for his troubles). From there, Bob Orton became a key cog in the storyline, serving as his son’s corner man, and getting involved in a number of physical altercations with The Undertaker.

The involvement of these WWE legends helped sell the immensity of the rivalry, complementing The Undertaker’s ever increasing status as a legend himself, while putting over young Orton and reminding fans of the Legend Killer gimmick that had brought him so much success earlier in his career.

3 3. Orton Claimed The Undertaker Had An Easier Time Being A Face Than Him

Years after the Randy Orton vs. The Undertaker rivalry had died down, Orton spoke in an interview about playing face and playing heel. He cited The Undertaker as someone who, particularly at this stage, had an easier time succeeding as a face. Not only was he a legend fans attached nostalgia to, but Orton cited that he had a unique and attractive character. Meanwhile, Orton had more his own personality and ring work to go on, and to make fans want to support him.

Fittingly, most fans seem to agree that Orton’s career work is better as a heel than as a face. Maybe that’s a testament to Orton being unlikeable, or maybe, as Steve Austin has often reinforced on his podcast, it’s easier for most guys to thrive as a villain than as a hero.

2 2. It Was Rumored The Undertaker And Orton Would Clash Again At WrestleMania 33

Come WrestleMania season, the Internet tends to get busy with fans speculating about what matches will take shape. The prevailing theory seemed to be that Randy Orton and Bray Wyatt might turn on each other to clash at the big show. Just the same, there was another vocal contingent that called for WWE to revisit the Orton vs. Undertaker issue.

Coming back to this feud would make some sense, particularly if WWE had kept Orton aligned with the Wyatt Family. Orton had won the Royal Rumble, but The Undertaker could have picked up the WWE Championship in the interim to justify the match up. Alternatively, WWE might have upheld Orton’s initial suggestion that he would relinquish his chance to challenge Bray Wyatt for the title out of loyalty to the Wyatt Family.

From a shoot perspective, coming back to Orton vs. The Undertaker might have done good business for WWE. While Orton was a rising main eventer in the original version of the feud, this time around it would legitimately be legend versus legend with two of the top stars of the last decade squaring off. It’s unclear how many more years The Undertaker might have in his tank; for now Orton remains on the short list of guys with the credibility to justify challenging him.

1 1. Orton Was Involved In Paul Bearer’s Last WWE Angle… And The Undertaker Wasn’t

The Undertaker’s career was profoundly intertwined with Paul Bearer. The guys worked together on smaller stages before coming to WWE, and then spent years together as a wrestler-manager pair when they got to the mainstream. When the two weren’t together, Bearer was often as not managing challengers to The Undertaker like Mankind, Kane, and Vader. Finally, Bearer became a recurring visitor to back The Deadman for special appearances or big returns.

Bearer would also return to contribute to Kane’s storylines, though, and it was in that role that he did his last work for WWE. When Randy Orton challenged Kane, he tried to get in the Big Red Machine’s head by kidnapping Bearer—Kane’s manager and kayfabe father—and locking him in a freezer. True to the eccentric and largely uncaring persona, when Kane found Bearer, he left him for dead, to show that Orton hadn’t really gotten in his head at all. WWE shot the angle in the spring of 2012. Sadly, Bearer would pass away in real life less than a year later.