Five Best Moments From Randy Orton’s 20 Year WWE Career

Randy Orton

Randy Orton has been in the WWE for 20 years this week. A wrestler rarely has a 20-year career, much less with the same company. 

Orton has floated between the main event and the mid-card throughout his career, with some highs and some pretty regrettable lows. So let’s look at 20 years of the Viper with some of his best moments. 

Related: Randy Orton Emotional Over Triple H, Kurt Angle Undergoing Surgery

His Debut 

Orton was born into wrestling. The son of Cowboy Bob Orton and Bob Orton Sr initially didn’t plan to wrestle and instead joined the Marines. That didn’t work out, so Orton entered the family business despite warnings from his family. 

Early on, the natural skill and athleticism were evident. Less than a year into the starting, he was signed by WWE and sent to the OVW developmental program in Louisville, Kentucky. 

At OVW, a young and cocky Orton trained alongside John Cena, Batista, and Brock Lesnar. After less than a year in developmental, Orton joined the main roster, where he wrestled in a few forgettable feuds. That all changed when he linked up with Ric Flair, Triple H, and Batista to form Evolution.

Joining Evolution 

Evolution dominated WWE for a brief time, representing the past, present, and future of wrestling, and led to Orton’ becoming the youngest World Champion in WWE history. His first of 14 WWE titles. 

Becoming The Legend Killer 

My favorite Randy, beating up on all the old-timers and emerging out of his family’s shadow to become of the most feared wrestlers in the game. And it was during this time that Randy began using his signature RKO.

From setting the Undertaker on Fire to that insane hardcore match with Mick Foley, Randy established himself as a legend in his own right. 

The Dark Years 

We can’t forget the dark times when Orton was constantly in trouble for causing trouble backstage or being popped for PEDs a few times. Randy was given too much too soon, and his immaturity caught him. Highlights from this time include Rated-RKO, Legacy, and on and off again feuds for the WWE titles. 

An Older, Wiser Viper 

Over the last five years, we have seen an old and wiser Randy Orton. Frequently taking up and comers under his wing, Randy has matured into a consistent fan favorite who continues to put on some of the most consistent matches in all of wrestling. 

I love his time with Riddle. I know they will break up eventually, but for the time being, I love seeing a calm and demurred Randy dealing with the Scrappy-Doo energy of Riddle.


And, of course, no article on Randy Orton will be complete without a celebration of the three most dangerous words in Sports Entertainment. There are so many to choose from, but I will show you my favorite. I’m biased because I saw this live in person, but hard to argue this one at WrestleMania on Seth Rollins isn’t the best.

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What’s your favorite Randy Orton moment? Share your thoughts in the comments below.

Hunter Patterson is a writer based in Los Angeles. He loves writing about pop culture, popcorn, and pro wrestling.... More about Hunter Patterson

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