At 71, Jake Roberts Named The 5 Hardest Wrestlers He Ever Faced

At 71, Jake Roberts names the five hardest wrestlers he ever faced. He carried a snake to the ring. He invented a move that ended careers.

He looked into the eyes of the biggest, the baddest, the most dangerous men alive. And he smiled. But five men made Jake Roberts question everything.

Most men who've lived the life Jake Roberts lived don't make it to 71. drug addiction, personal tragedy, physical destruction, a wrestling career that spanned four decades across every major promotion on Earth. He's been through wars that would have broken ordinary men before the first bell even rang.

But here's what most people don't ask and what Jake almost never answers. Which men specifically made him sweat? Which opponents got inside his head?

Which five wrestlers forced Jake Roberts, the master of psychological warfare, to fight on someone else's terms? Today, we have those five names, and the stories behind them will change how you think about an entire era of professional wrestling. This is the countdown from hell.

Number five, Ricky the Drgon Steamboat. May 1986, Saturday night's main event. 50 million American households watching on NBC.

Jake Roberts had been in the WWF for barely two months. He was still building his reputation, still establishing The Snake, and Vince McMahon handed him the keys on national television. What happened that night became legend.

Jake planted Ricky Steamboat with the DDT on the concrete floor right in front of Steamboat's wife, Bonnie, whom Jake had pointed to just before delivering the blow. Steamboat didn't just go down. He was knocked unconscious.

He sustained a concussion. The arena went silent. Now, here's what most people forget.

Jake Roberts didn't want to do that spot. He was genuinely afraid he'd injure Ricky Steamboat for real. maybe permanently.

It only happened because Ricky Steamboat himself looked Jake in the eye and said, "I trust you. I can protect myself. " That moment, that exchange of trust between two men in a business built on deception tells you everything about why this feud was so brutal.

Because Steamboat was the one opponent Jake could never truly rattle. Other guys, Jake could get inside their heads. The snake, the promos, the darkness.

It worked with Ricky Steamboat. Jake threw everything at him and Steamboat came back every single time. Steamboat won almost every match in that feud.

Jake won exactly one by count out and even then only because Steamboat threw him back in the ring and didn't make it back himself in time. For a man whose greatest weapon was psychological superiority, facing someone immune to psychological warfare is by definition the hardest opponent you can face. Ricky Steamboat didn't just challenge Jake physically.

He challenged what Jake believed about himself. That's why he's number five. Number four, ravishing Rick Roode.

If Ricky Steamboat challenged Jake Roberts in the ring, Rick RDE went after something far more dangerous. He went after Jake's wife. On the April 23rd, 1988 edition of WWF Superstars of Wrestling, Rick Roode, as part of his gimmick, picked a woman from the crowd to kiss after his match.

That woman happened to be Cheryl Roberts, Jake's real life wife. She refused. RDE insulted her.

And when Jake came to her rescue, a feud was born that no Booker had planned because it was real. Then Rude escalated. He had Cheryl's face airbrushed onto his tights.

He wore her image to the ring every single night and he kissed those tights on national television. Jake tore them off rude mid-match on live television in a moment so raw and so personal that the crowd didn't know whether to cheer or hold their breath. But here's the layer that makes Rick RDE number four on this list.

RDE was pound-for-pound one of the most physically perfect athletes in WWF history. 6' 251 lb of chiseled muscle. He could work a crowd and he could actually wrestle.

He wasn't just a character. He was a legitimate physical threat every single night. And unlike most of Jake's opponents, RDE didn't wilt under pressure.

He turned the heat back on Jake. He made it personal from his side, too. And a feud where both men genuinely cannot stand each other is a completely different animal than a working rivalry.

Jake has spoken about this feud multiple times over the years. The anger was real. The motivation was real.

And when the motivation is real, so is the danger. Rick RDE made Jake Roberts walk to that ring with his heart rate elevated before the first bell even rang. That's why he's number four.

We're three names away from the top. And the further up this list we go, the more the word hard stops meaning physical. It starts meaning something deeper.

The next three men on this list left marks that no amount of time has ever fully healed. Number three, Andre the Giant. 7'4 in tall, 520 lb.

When the WWF told Jake he'd be working a program with Andre, Jake's first reaction, his own words, was, "Are you freaking kidding me? " Because working a match with Andre the Giant wasn't really a match in any traditional sense. It was an experience, an ordeal.

Andre didn't give you anything in the ring, nothing. You couldn't predict him. You couldn't plan around him.

And if Andre decided he didn't want to go somewhere, you weren't going anywhere because there was simply no mechanism available to the human body to move Andre the giant. So Jake did what Jake always does. He found the psychological lever.

He discovered, or at least he convinced the entire world, that Andre the Giant was terrified of snakes. On national television, Jake unleashed Damian on Andre and the eighth wonder of the world crumbled. He fell to the mat.

His body shook. Bobby Heenan pounded on his chest trying to restart his heart. The arena went absolutely silent.

50 million people believed they had just watched Andre the Giant suffer a cardiac arrest. It was theater. Andre knew it was theater.

But here's what most people don't know. Years later, Jake admitted that the snake did bite Andre during their time together. The fangs got stuck in Andre's shoulder, and Andre, all 7'4 of him, didn't even flinch.

A man who can absorb a snake bite and keep his face perfectly still, is not a man you want to be alone in a ring with. At Wrestlemania 5, Jake hit the DDT on Andre the Giant, the move that had put every man he'd ever faced down for 3 seconds. and Andre didn't go down cleanly.

Jake couldn't fully execute it because you cannot DDT 520 lbs the same way you DDT a normal human being. Jake won that match by disqualification, not by pinfall, not by submission because Andre attacked the referee against the eighth wonder of the world. A disqualification was the best result available.

Number three. Number two, Macho Man Randy Savage. This is the one that surprises people because when most fans think about Randy Savage and Jake Roberts, they think about Jake as the aggressor, the villain, the snake.

They see Jake crashing the wedding, sending a cobra as a gift, making Miss Elizabeth scream. They forget what it actually cost Jake Roberts to be that villain. SummerSlam 1991.

Randy Savage and Miss Elizabeth got married on WWF television and Jake Roberts playing the most effective villain in wrestling at that moment crashed that reception with the Undertaker and unleashed a live cobra. The country lost its mind. Elizabeth's parents watching at home were so horrified by what Jake Roberts was doing to their daughter on national television that they put enormous pressure on the WWF to shut the entire feud down.

But before any of that happened, Jake Roberts had to prove to Randy Savage that the cobra was devenomized before Savage would agree to the angle. And Jake's method of proof was simple. He lifted his own pant leg and he let the cobra bite him to show Randy Savage it was safe.

That is the level of professional commitment this man operated at. But Randy Savage was equally committed. And here's why Savage is number two.

Randy Savage was one of the most intense, most driven, most physically committed human beings in the history of professional wrestling. He trained obsessively. He prepared obsessively.

He worked obsessively. In the ring, there was no off switch. Jake has spoken about working with Savage.

When you're in there with Randy Savage, you are always at 100%. Because Savage simply does not know another speed. There's no coasting, no easing into it.

From the opening bell to the final bell, Savage gives everything he has every single second. At this Tuesday in Texas in December 1991, Savage won their PPV match. And afterward, Jake escalated to territory that genuinely shocked an industry not easily shocked.

He slapped Miss Elizabeth on camera in front of millions of people. The heat was so nuclear, so personal, so real that it stopped being a wrestling feud. It became something else entirely.

Jake has been open about his frustration that the feud ended too soon, that Elizabeth's parents put pressure on the company, that he and Savage never got the Wrestlemania blowoff match they deserved, a match that, by Jake's own admission would have kept him in the WWF. A feud that was emotionally draining, physically punishing, politically complicated, and ultimately unfinished. Randy Savage.

Number two. There is one man left. One man who above all others pushed Jake Roberts to his absolute limit.

And he was not supposed to be on this list. Number one, the Undertaker. In 1991, Jake Roberts helped build the Undertaker.

Think about that sentence. The Undertaker debuted at Survivor Series 1990. He was young.

The character nobody had ever seen before. But the mythology was still being written. The dead man was still becoming the dead man.

And the man chosen to help write that story. Chosen to help develop one of the greatest characters in wrestling history was Jake Roberts. Jake became the Undertaker's dark partner in one of the most psychologically complex storylines WWF had ever attempted.

He guided the ultimate warrior through a series of tests, a coffin, a buried alive segment, a room filled with live snakes, a treasure chest. It was psychological horror storytelling decades before WWE regularly attempted anything close to it. And then Jake turned, revealed he'd been working with the Undertaker all along, and closed the final segment with the line that still gives people chills.

Never trust a snake. The problem was now Jake had to face the monster he helped build. Wrestlemania 8, March 29th, 1992, Indianapolis.

This was Jake Roberts last match in his first WWF run, and the opponent was the Undertaker. Jake hit the DDT twice. The move that had put every man he'd ever faced down for 3 seconds.

The move that was not just a finisher, but a statement, a full stop at the end of a sentence, a declaration that said, "This is over. " Every single time it landed, the Undertaker sat up. Think about what that moment does to a man.

Jake Roberts had built his entire psychological identity around one truth. The DDT ends it. No exceptions, no arguments.

The DDT ends it. That certainty was the foundation of everything. The promos, the confidence, the willingness to walk into any arena in the world and face any man alive.

All of it rested on that one unshakable fact. And the Undertaker sat up. Jake hid it again.

The Undertaker sat up again. The Undertaker rose, hit the tombstone pile driver, and Jake Roberts stayed down. It wasn't just a loss.

It was a dismantling of the one psychological certainty Jake had carried through his entire career. The Undertaker didn't just beat Jake Roberts that night. He broke the myth.

But here's the layer that makes this number one and the reason it sits differently than every other name on this list. Jake Roberts helped build the Undertaker. He was part of the architecture, part of the mythology.

He helped hand Vince McMahon the blueprint for one of the most enduring characters in the history of professional wrestling. And then that creation, the thing he helped build, the monster he helped bring to life, turned around and ended his chapter. There is no harder opponent than the one forged from your own hands.

The Undertaker. Number one. Five opponents.

Five different kinds of hard. Ricky Steamboat, the man the psychological warfare couldn't touch. Rick RDE, the man who made it personal.

Andre the Giant, the man physics protected. Randy Savage, the man who burned everything down and still came back for more. And the Undertaker, the man Jake helped create, who turned around and closed the book on that era of his career.

Jake Roberts spent a lifetime telling other people's stories in that ring, weaving darkness and psychology into something that felt more real than real life. What he rarely admits is that his greatest story was always his own. He was bitten.

He fell. He stayed down. And then slowly, painfully, on his own terms, he sat back up.

Maybe he learned that from the one man he couldn't beat. Jake the Snake Roberts was inducted into the WWE Hall of Fame in 2014. He is 71 years old.

He is still talking. If you want more deep dives into the untold stories of wrestling's greatest era, subscribe. The next one drops soon.

And trust me, you're not going to see that one coming either.