As a WWE fan of around 25 years and with an extensive knowledge of the company’s history, I have seen a lot. A lot of good and a lot of bad. A lot of squeaky clean baby-faces and a lot of downright dirty heels. I challenge anyone to find me a more dastardly heel than Randy Orton. Orton burst onto the scene way back in 2002, carving out a hall of fame career littered with its fair share of despicable moments. A pretty controversial figure both in and out of the ring, Orton has certainly given us a lot to talk about over the years and a lot of memorable moments inside the squared circle.

In a mix of shocking, disgusting, memorable and downright dirty moments, join me as I run down my personal Top 10  list of Randy Orton’s Most Despicable Deeds!

10. The ultimate sign of disrespect.

In a moment that Carlito would be proud of, Orton committed an act that a lot of people deem to be the most disgusting you can inflict on another person. We watched in shock as Orton spat in the face of the hardcore legend Mick Foley and then took it a step further doing the same thing to Harley Race. This led Triple H to demand that Orton handed over his World Heavyweight Championship, Did Randy listen? Hello no! Hunter was the next in line to literally feel the venom of the Viper.

9. The 2^nd dirtiest player in the game.

Remember Rated RKO? One of the most dangerous tag teams we have ever seen with a phenomenal resume to prove their credentials, the tandem took things a step too far when they attempted to cave in Ric Flairs skull. The “Nature Boys” head was “crushed like a grape” after a brutal attack, with Randy & Edge delivering a brutal Conchairto. Arguably the greatest to ever lace his boots, there was surely no better target than Flair for solidifying yourself as the top heel team in the business.

8. You can’t see him…

Showing that being a great heel doesn’t just come from spitting vitriol into a microphone, Orton would physically decimate John Cena after the leader of the Cenation tore his pectoral muscle in a match with Mr. Kennedy, Orton targeted Cena’s injury after the match, delivering two brutal RKOs along the way and putting Cena on the shelf for a number of months, in turn forcing him to vacate the title that Orton himself would later go on to win. Taking out the ultimate babyface? That’s a sure fire way to solidifying yourself as the top heel in the company.

7. Setting The Undertaker on fire

If you want to make a name for yourself, who better to go after than The Phenom? Randy and his hall of fame father, “Cowboy” Bob Orton, had not long defeated The Undertaker in a two-on-one handicap casket match when Randy sent the ultimate message by setting the casket on fire. If there had been any doubters to Orton labeling himself the “Legend Killer”, they were certainly silenced here.

6. The girls just keep falling for him…

Way back when, there was a period in time when Randy was actually a believable babyface who you didn’t expect to betray you at a moments notice. This was all set to change though as Orton struck his then-girlfriend Stacy Keibler with the most “out of nowhere” RKO you’ve ever seen. Not content with taking out his better half, Orton would take things to the next level when he gave the Fabulous Moolah a beautiful birthday present – an RKO – in front of her hometown fans.

I’m sure he bought her some flowers too… erm…

5. The Undertaker’s last ride

Not content with trying to burn The Deadman to a crisp, Orton dragged the legends carcass onto the back of the recently departed Eddie Guerrero’s low-rider, Randy then drove Taker straight through the SmackDown stage in another heinous attempt to kill a legend. While the attack itself was bad enough, this one struck a chord through the WWE Universe. The disrespect on show, using Latino Heats prized possession, elevated Randy to a new level of heeldom. You must be thinking “there’s no way he would disrespect Eddie any further…”

4. Insulting the legacy of Eddie Guerrero

Well you’d be wrong! How about driving that very low rider out on to the stage? How about reading out offensive quotes from Eddie’s biography? Yep, Orton once again stepped things up and sunk to a level further than we could have ever expected. I will never forget the exact moment when he told Rey Mysterio that Eddie Guerrero was residing in hell and not in heaven. I was absolutely shocked, angry and devastated… all of the things a heel is meant to make you feel. A truly disgusting act that Orton pulled off to absolute perfection.

3. Ears to you Jeff.

Now this one made me feel a bit queasy, something that doesn’t happen often. During his feud with Jeff Hardy, Orton disgustingly tortured the charismatic enigma by pulling at his ears and spacers for weeks. However, this was taken to the Xtreme (get it?) during their subsequent hell in a cell match when Orton would insert a screwdriver into Hardy’s earlobe and twisted it vigorously. I can still picture the uneasy faces of the people in attendance. This was Orton at his psychotic, deranged best.

2. Punting John Cena’s father in the head

Ah… The Punt. The most brutal attack In Orton’s arsenal. Rightfully outlawed, the punt kick was responsible for taking out many respected legends. However it found a new unexpected victim after Orton lost his title to John Cena at SummerSlam 2007. Vince McMahon would lay down a challenge for Orton, demanding that he proved himself worthy of another title shot. It was here that Orton would make an impact that sent shock waves through WWE and especially the Cena family.

With John Cena at his mercy, Orton lined up a devastating punt to the head, but to everyone’s surprise he would stop just short of the delivering the fatal blow. Instead, Orton rolled out of the ring, grabbing Cena’s father from over the barricade and punting him in the head at ringside before simply walking away. Calculated, cruel, disgraceful… perfect.

1. Rated RK… Oh…

Spoilers ahead for anyone who hasn’t seen the 2020 Royal Rumble yet but… what the hell are you waiting for?

I don’t like to rank peoples misery (yes I do) but I think it’s safe to say that Edge’s sudden retirement in 2011 was the most heartbreaking case of a superstar stepping away before their time. Edge was on top of the mountain at the time, having to relinquish his championship as a result of doctors warning him that further in ring activity could potentially kill him. Nobody saw Edge returning. Daniel Bryan did it sure, but Edge… no chance. That was until the most unbelievable return OF ALL TIME as Edge entered the Royal Rumble match to a thunderous ovation the likes of which you will rarely see.

This past Monday Night Raw saw Edge appear and address the crowd of his situation and his intent to return to active competition. Edge was interrupted by longtime friend and former tag team partner Orton, who hit the ring to welcome home his compatriot. Orton would then tease getting the band back together before striking Edge with one of his famous RKOs. Not intent on betraying one of his closest allies, Orton would deliver another crushing Conchairto to the previously injured and rehabilitated neck of Edge, resulting in some of the most furious heat I have ever heard. What made this so special was Orton’s performance throughout, his face painted with discomfort, despair and doubt. He sold this attack to perfection, showing that even he knew he had gone way too far this time.

So those were my personal Top 10 despicable deeds in Randy Orton’s long and illustrious career. Most superstars would be happy to have 1 or 2 of those over the course of their time in WWE, but I had to cut out at least another 15. Randy Orton has set himself apart and proved himself to be the greatest heel of his generation. Possibly ever other generation before him too.