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Randy Orton’s Most Despicable Moments in WWE

Originally posted on Last Word On Sports
By Shiraz Aslam | Last updated Mar 15, 2026 10:33 AM ET

Randy Orton is a 15-time World Champion, a 2-time Men’s Royal Rumble winner, and a Grand Slam Champion. Orton has a stacked resume, but the Viper didn’t achieve these accomplishments by playing nice. Rather, he has found more success as a despicable heel.

His iconic theme song clearly states that he “hears voices in his head.” Unfortunately for the WWE roster, those words are absolutely true. When Orton becomes unhinged, he is a psychopath with no morals who will cross all boundaries to get what he wants. The 15-time World Champion recently turned heel and betrayed Cody Rhodes.

The WWE Universe can expect Orton to pull off some disdainful acts. While it’s difficult to underestimate his menace, it would be difficult, even for Orton, to top these despicable acts.

#5. Randy Orton Burned The Undertaker Alive in a Casket

As the son of Cowboy Bob Orton and mentee of Triple H/ Ric Flair, Randy Orton was always destined for greatness. However, a main-event-level feud with The Undertaker in 2005 showed everyone what Orton could do atop the card.

Taker defeated Orton at WrestleMania 21 in an underrated gem. This was the beginning of their long program. The Viper would cost the Phenom the WWE Title and play his own set of mind games. Through some shenanigans, the Legend Killer also defeated Taker.

Nonetheless, he outdid himself at No Mercy 2005. The father-son duo of Bob and Randy Orton battled The Undertaker in a Handicap Casket match. The Ortons won the match by successfully closing Taker in the casket, but they weren’t done. After destroying the casket with an axe, the Viper set it on fire, effectively committing murder on live TV.

Eventually, The Undertaker returned for vengeance. However, Orton’s actions spoke volumes about his desperation and unscrupulousness. The Legend Killer would not hesitate to kill his rivals if they posed a serious threat to him.

#4. Orton Punted John Cena’s Father in the Head

The worst part of Randy Orton’s run of terror in the late 2000s is that he grew more dangerous with each passing year. In 2005, he was burning the Deadman in a casket. By 2007, he was terrorizing and physically tormenting a middle-aged businessman just because he was John Cena’s father.

John Cena Sr. was casually sitting in the front row watching a match between his son and Booker T. Things took a turn for the worse when Orton interfered and attacked Cena. Although it appeared as if the Viper would punt the Champ in the skull, he quickly turned his attention to the front row.

The unhinged Viper pulled Cena’s father over the barricade and nearly kicked his skull off his body. It looked brutal and left fans appalled. Getting physical with a non-athlete is already deplorable, but nearly concussing them is a heinous crime.

#3. The Viper DDTs and Kisses Stephanie McMahon

By 2009, no one was safe from Randy Orton, not even the McMahon Family. The Viper began feuding with his bosses in the early part of the year. It started with verbal insults, but quickly got physical in an ugly way. Vince McMahon was about to fire Orton, but was instead met with a Punt Kick.

Stephanie McMahon brought back her brother, Shane O’Mac, to neutralize the Randy Orton problem. However, Orton had two loyal partners in Cody Rhodes and Ted DiBiase Jr. Together, the Legacy easily dismantled Shane McMahon’s resistance. Finally, Triple H entered the fray, but he had to pay a heavy price for being the savior.

During a Handicap match on RAW, Orton handcuffed HHH to the rope. He was about to attack his WrestleMania opponent with a Sledgehammer before Stephanie McMahon came out to save her husband. This was an ill-advised move. Rhodes and DiBiase cornered HHH’s wife, and Orton delivered a draping DDT on Stephanie.

When things couldn’t get any uglier, the Viper kissed the fallen Stephanie McMahon as Triple H looked on helplessly with anger and the crowd was appalled beyond measure.

#2. The Miz’s Parents Are Forced to Watch Their Son Being Destroyed

Over time, it felt as if Randy Orton had toned down and controlled himself to a degree. However, there were occasions when he still heard voices in his head. Orton became a corporate WWE Champion at SummerSlam 2013 by aligning with Triple H and forming the Authority.

Over the next few months, the Authority would dominate the roster, and Orton had a free pass. With unlimited power at his disposal, Orton showed a more remorseless side of himself. While Daniel Bryan was his prime target, The Miz also had to endure Orton’s brutality.

On an episode of RAW in September 2013, the A Lister was picked apart and destroyed by Orton in front of his parents. The Miz’s mother looked on in tears helplessly as the WWE Champion dismantled her son.

#1. Orton Nearly Ends Edge’s Career Once Again

The 2020 Men’s Royal Rumble holds a special place in the hearts of hardcore WWE fans. After a 9-year retirement, Edge finally returned to the ring. Everyone was happy except for a jealous, selfish, and unhinged Randy Orton, who the Rated R Superstar had eliminated from the Rumble.

Edge made his return to RAW the night after the Rumble. Orton appeared to congratulate his friend and proposed a Rated RKO reunion. However, the Hall of Famer should have known better. The Viper delivered a thunderous RKO and unleashed a brutal assault that resulted in a Con Chair To to the skull.

The Viper betrayed his friend, but his intentions were clear. Orton wanted to force Edge back into retirement and send him back home to his kids and wife. This was the beginning of yet another epic heel run for the Apex Predator.