24 Years Of The Viper: Randy Orton Hits 24 Years In WWE

Chris King takes a look back at some of the most iconic feuds of Randy Orton and his 24 years in WWE.

Twenty-four years ago, Randy Orton made his debut on the April 25th episode of Friday Night SmackDown against the veteran Hardcore Holly. ‘The Viper’ has had a decorated career in WWE: grand slam champion, a fourteen-time world champion, two-time Royal Rumble winner, former Money in the Bank, and multi-time tag team champion. Here are some of Orton’s most iconic feuds in WWE. 

Randy Orton vs. Mick Foley 

The ‘Legend Killer’ was so disrespectful to Mick Foley by verbally abusing him and spitting at him. Foley retired in 2093 but made his shocking return at the 2004 Royal Rumble, eliminating Orton. The two superstars would begin a heated rivalry at WrestleMania XX, where Evolution (Randy Orton, Batista, and Ric Flair) would face off in a six-man tag team match against The Rock and Mick Foley. Orton’s victory would continue his ascension through the WWE, but it also continued his feud with Foley. Foley would take Orton to hell with him at the 2004 Backlash PLE. 

Both superstars would have a No Holds Barred Falls Count Anywhere match, which Orton himself considers one of his favorite matches of his career. 

The legend helped solidify Orton as a top heel in the company, where people had some misconceptions that a pretty boy couldn’t get hardcore and messy against the hardcore legend. Without their iconic feud, perhaps Orton’s greatest achievement may not have happened. 

Randy Orton vs. Triple H 

Evolution’s leader Triple H had been telling Orton that he was the diamond in the group. Orton was so appreciative of his mentor’s support as he challenged Chris Benoit at the 2004 SummerSlam PLE. Orton would shock the world by becoming the youngest world champion in WWE history. The very next night after a successful defense, Evolution came out to celebrate with him. With Orton on Batista’s shoulders, his world turned upside down with the iconic “thumbs down” moment. HHH went from friend to rival in seconds, bloodying up his protege out of pure jealousy and rage. The two would have a mini feud where HHH would take the world title away from Orton. 

The rivalry was restarted after ‘The Viper’ hit Vince McMahon (HHH’s father-in-law) with a vicious punt kick after he was about to fire him. Orton, along with his two Legacy stablemates Cody Rhodes and Ted DiBiase Jr., made it his life’s mission to destroy the McMahons, including

Shane McMahon and HHH’s wife Stephanie McMahon. The Viper blamed IED for his actions, but in reality it was Orton getting his ultimate revenge against his former mentor when he was viciously kicked out of Evolution. 

Randy Orton vs. The Undertaker 

In 2005, The Legend Killer was looking to do the impossible when he challenged The Undertaker to a match at WrestleMania 21. Orton was young and arrogant and was trying to do everything to break his rival’s undefeated streak at WrestleMania, but The Phenom got the job done. During the match, Orton’s father Bob Orton Jr. tried to help his son win. At SummerSlam, Orton and Undertaker would do battle again; this time, Orton’s dad would be disguised as a fan, and The Legend Killer would get the victory. 

At No Mercy, both Ortons would face Undertaker in a casket match. Orton won the contest, and as his rival lay in the casket, they lit it on fire. 

A few months later, The Deadman would make his shocking return at the 2005 Survivor Series PLE after Orton was named the sole survivor for his team. Taker rising through the fire and kicking the casket open was one of the coolest moments in WWE history. Orton thought he had the last laugh, but in true Taker fashion, he challenged him to a Hell in the Cell match. Orton with nowhere to hide inside the demonic structure, as The Phenom finally got his revenge. 

Randy Orton vs. John Cena 

This rivalry was the next generation’s Stone Cold vs. The Rock because it spans throughout the years. Orton vs. Cena was simply both GOATs trying to prove who was at the very top in the company. This storied rivalry began in 2007, when Cena was the WWE Champion and Orton was challenging him at SummerSlam. Cena would retain it, and The Viper struck back, delivering a vicious punt kick to Cena’s father, who was at ringside. They would feud for a few months until Cena got injured and needed surgery. 

All throughout 2008, both rivals would go their separate ways until the following year. After Orton’s vengeance was successful at the 2009 Backlash with winning the WWE Championship, his and Cena’s rivalry was restarted. They competed in a series of matches throughout the summer. Their iconic I Quit Match, a 60-minute Ironman Match, will go down in history as one of the greatest of all time. Cena would finally get his comeuppance inside Hell in the Cell by winning the WWE Championship. This would put a pause on their rivalry. 

Both superstars would find their way back to each other in 2014, when Orton won the WWE Championship after cashing in his MITB briefcase on Daniel Bryan. The Viper was the focal point of The Authority (Triple H, Randy Orton, and Stephanie McMahon), and Cena once again was the thorn in his side. Cena had won the World Heavyweight Championship, and this was building to a huge title unification ladder match. Both superstars would utilize everything in their arsenal, but Orton handcuffed his rival’s hand to the ring ropes. Cena went crashing through the table, and The Viper claimed both titles. 

In 2025, Cena would do the unthinkable and turn heel, which shocked the world. Mr. ‘Never Give Up’ actually gave up on his fans and verbally attacked everyone for wanting to be like him. While the self-proclaimed GOAT was gloating about defeating Cody Rhodes to become a seventeen-time WWE champion, an old rival snuck up behind him and gave him an RKO! The two longtime rivals would face off one final time at Backlash inside Orton’s hometown. Their match wasn’t incredible because Cena was still trying to find his footing as a top heel. Cena would retain the title, and sadly, this is how one of the greatest rivalries in WWE history ended.