Summary

• Randy Orton's rise from wrestling royalty to WWE legend showcases his unique in-ring ability and natural "smoothness."
• Orton's classic matches with Triple H, Jeff Hardy, and The Undertaker solidify his legacy as a future Hall of Famer.
• Orton's memorable encounters with John Cena, Shawn Michaels, and Cactus Jack highlight his versatility and willingness to push boundaries.

Randy Orton was always primed for potential in WWE, but even his biggest ers could not have imagined just how big he'd become as a wrestler. Early into his career, he was best known as the son of Bob Orton Jr. but has withstood the test of time to the point it's easy to forget that he comes from wrestling royalty. In recent years, even skeptic fans started to recognize Orton's unique and incredible in-ring ability, often defined by his colleagues as a natural "smoothness" that every pro wrestler strives to obtain, while Randy had it from the start.

Randy Orton ended up carving a path for his legacy that's bigger than that of the Orton namesake. A third generational superstar referred to as Legend Killer, then Viper, Orton has done a lot for himself since debuting in 2002. He's since become a movie star, a beloved internet meme (#RKOOuttaNowhere), and of course, a 14-time World Champion. Safe to say, Randy Orton is a future Hall of Famer. Someone as good as Orton doesn't get as far as he does without a few classic matches under his belt, like these.

10 Randy Orton vs. Triple H

No Mercy 2007 - Last Man Standing Match

WWE's first coronation of Randy Orton with his first WWE Championship was an ambitious attempt, but impressive storytelling on short notice. After champion John Cena is injured days before the show, No Mercy opens with Vince McMahon awarding his would-be-challenger, Orton, the title by default. He then loses it in a title defense minutes later to Triple H, who defends against Umaga later in the night. To close the show, Orton evokes his rematch clause in a main event Last Man Standing match.

The story of a vigilant babyface trying to fight back underneath a sadistic heel with his eyes on the prize never gets old, and it makes for what is, by far, The Game and The Viper's best match against each other, compared to the wars they would have years later.

9 Randy Orton vs. Seth Rollins

WrestleMania 31

It's hard to think about this match and not think about what many are still calling the best RKO outta nowhere. That moment is the biggest talking point about the match, but that shouldn't let fans overlook the match itself. Going into this, Orton was practically at his peak as a seasoned vet while Seth Rollins - the modern Mr. WrestleMania - was having his first WrestleMania singles match, still in the prime of his career.

Seth Rollins had a lot to prove with the lights on bright, while Orton was in a position to make his opponent look like a million bucks. As much as the match is best known for a tremendous spot, there is more to the match than just the spot. Story-wise, Orton had to overcome an interfering J&J Security to get his hands on a sniveling Architect.

8 Randy Orton vs. Jeff Hardy

Hell in a Cell 2018 - Hell in a Cell Match

Randy Orton's 2008 fast-paced WWE Championship match with Jeff Hardy at the Royal Rumble event is just as deserving of a mention, but what these men do in this match to each other is essential viewing, even if it's not for the faint of heart. There is a saying in wrestling about how a wrestler - especially in a hardcore setting - may throw everything but the kitchen sink at their opponent. Inside of the Hell in a Cell, Orton and Hardy threw everything at each other, including the screwdriver.

At a time when wrestling fans were convinced that modern Hell in a Cell matches had become far too tame, these two delivered an uber-violent affair that made the Hell in a Cell its own character into the story, utilized to perfection.

7 Randy Orton vs. Undertaker

WrestleMania 21

Some of the best years of Randy Orton's career came as the Legend Killer. For a rising star in the industry, this was the perfect character. A young rookie hoping to make a name for himself at the expense of legends on the roster. The concept reached its highest potential when he challenged not only the legend of The Undertaker, but the legendary WrestleMania undefeated streak of The Phenom.

While Taker's Streak had been mentioned in the past, this would be the first time that someone would wrestle him on the Grandest Stage specifically to challenge his undefeated streak, something that would become a staple of his feuds for future WrestleMania. This match would become surprisingly influential in that regard, but it's Orton's performance with a respected veteran of the sport that would help the Legend Killer carve out a path for legend status.

6 Randy Orton vs. Batista vs. Daniel Bryan

WrestleMania XXX - Triple Threat Match

This main event capped off a larger story of the night. Not necessarily just in of Daniel Bryan's earlier match in the night, but the story that anything could happen at WrestleMania. Within the hour before this began, Undertaker's Streak had just ended, something that wrestling fans everywhere would have been certain would never happen. When it appeared to be a given that Daniel Bryan would get his moment, Undertaker's unexpected loss cast a shadow of doubt over this match.

That only helped add a level of drama to this bout. As for the match, if anyone needs props for it, it's Randy Orton. Going into the match, the champion was nearly overshadowed, with Bryan and Batista being the bigger talking points on the Road to WrestleMania, but he refused to let it affect his performance.

5 Randy Orton vs. Christian

SummerSlam 2011 - No Holds Barred Match

When Christian won the World Heavyweight Championship in honor of his retired best friend, no one would have expected him to become the most hated heel of the summer. Then again, no one expected him to lose the title two days after winning it. Somehow, though, one of the more controversial moments from the PG Era was able to turn into a tremendous rivalry.

Both Randy Orton and Christian are two of the most underrated in-ring performers in WWE history, due to their smooth but also not-flashy style. As their chemistry strengthened and their feud intensified, their matches only got better and better, with the finale of their rivalry proving to be their best match. For anyone looking for a pure in-ring wrestling contest, their match at Over the Limit might be the best, but for anyone wanting an in-ring masterclass mixed with unrelenting violence, then their No Holds Barred bout at SummerSlam adds a whole new layer to the cake.

4 Randy Orton vs. John Cena

Breaking Point 2009 - I Quit Match

John Cena and Randy Orton have had enough matches to fill out this entire list, even at the begrudgement of most viewers. By 2009, these two had wrestled each other so many times that fans were getting sick of the same pairing at every pay-per-view. In fairness, the reason why these two feuded so often was because their chemistry was so sharp. Much like The Rock and Steve Austin before them, the two flagbearers of this company just had too much rich history to not revisit.

However, out of all their matches, this is the one that strikes the biggest chord with audiences. Whenever people online say, " 09 Orton?" They have this match in mind, as his vicious onslaught over Cena is almost uncomfortable to watch, but nonetheless gripping.

3 Randy Orton vs. Edge vs. Shawn Michaels vs. John Cena

Backlash 2007 - Fatal-4-Way Match

If any match could lay claim to being the best Fatal-4-Way match in WWE history, maybe even wrestling history, this would be a strong contender. All four men have gravitated around the WWE Championship in the fallout of WrestleMania 23. Shawn Michaels wanted his rematch against John Cena, Randy Orton wanted John Cena, and Edge dubbed himself the uncrowned number one contender after Orton and Michaels pinned each other in a number one contender's match on the April 9th episode of Raw.

This dispute could only be resolved with this stipulation, which was littered with non-stop action. It all reaches a crescendo in an unforgettable finish, where each opponent unleashes a barrage of finishers until John Cena gets knocked out onto Orton for a pinfall victory.

The exciting climax of this match was so great that it appears to have inspired NXT Heatwave 2024's Fatal-4-Way finish.

2 Randy Orton vs. Shawn Michaels

Survivor Series 2007

When Randy Orton finally won the WWE Championship later that fall, he and Michaels would continue feuding, especially after Orton put The Heartbreak Kid on the shelf in May's Judgment Day event, not returning until the October 8 episode of Monday Night Raw. After a string of matches ended in Orton intentionally disqualifying himself to retain, their Survivor Series match was given this stipulation: if Orton disqualifies himself, HBK wins the title, but if Michaels uses the Super Kick, he is the one that's disqualified.

It was interesting to see Michaels actively trying to brainstorm ways to incapacitate Orton without his all-time great finisher, the Sweet Chin Music. These are two of the best in-ring performers that the company ever saw, so it's natural that the culmination of their feud would be spectacular. Plus, the story of Michaels being torn between wanting the WWE Championship and wanting to inflict revenge is captivating from bell to bell.

1 Randy Orton vs. Cactus Jack

Backlash 2004 - Hardcore Match

Going into this match, Randy Orton had a perception of him as a wrestler. As most audiences expected him to be the company's golden boy primed for greatness, he hadn't proven himself yet, and therefore, was just pegged as a pretty face. That would all change at Backlash 2004, where he decided to get a little hardcore. A month removed from pinning Mick Foley at WrestleMania's Handicap Match between The Rock n Sock Connection and Evolution, Foley would pull his Cactus Jack shirt out of the closet to beat respect into this rookie.

This performance has been lauded as one of the best Hardcore matches in the history of the company, and for good reason. The imagery from this match - like Randy's back bump onto thumbtacks - remains iconic. Orton showed he wasn't afraid to get dirty, violent, and most of all, bloodied. This was considered Randy Orton's breakout performance as a singles star, and it still holds up as one of his career-best performances in WWE.