On Raw, CM Punk committed his greatest transgression yet, brutally assaulting The Undertaker and dumping the contents of Paul Bearer’s urn on him. Relive some of WWE's other most dastardly all-time deeds, including fiery assaults, heartbreaking betrayals, grave mistakes and more of the most heinous crimes ever perpetrated in WWE!

Sins of the Ring

There are moments of glory the WWE Universe will always remember. Hogan slamming Andre. Eddie winning the WWE Championship. Then there are moments they can't forget — the double crosses, heartbreaking betrayals and fiery assaults that remind us how dangerous a career in WWE can truly be. In this Top 25, WWE.com looks back in anger at the most sinister things ever done in and out of the squared circle. Enter at your own risk.

Chris Jericho breaks into television

As a boy growing up in the frigid northern expanse of Winnipeg, Manitoba, Canada, Chris Jericho idolized Shawn Michaels. The fame, the good looks, the talent — Jericho wanted it all. So what led him to smash his hero’s face into the “Jeritron 5000” television screen live on Raw in September of 2008? If you believe the nefarious Superstar, it was retaliation — a justified act done in response to HBK faking an injury to beat Batista one month prior. In reality, it was envy. Despite years of success in the squared circle, Jericho knew he would never be able to achieve the greatness of his idol and in order to deal with these shortcomings he would annihilate Michaels. Y2J never did destroy the legend, but he came close — HBK suffered an eye injury that night that was so severe, he was almost forced to retire.

Team Lay-Cool starts a war of words

When Michelle McCool and Layla said they were going to make Mickie James’ life a living hell on SmackDown in late 2009, they weren’t kidding. After cutting up her ring gear with scissors and attacking her in the locker room, Team Lay-Cool did their worst on SmackDown in November of 2009 when they made a video that would permanently scar the southern belle. Creating their own version of the nursery rhyme “Old MacDonald,” the mean girls superimposed Mickie’s face on a swine and christened her “Piggie James.” Sticks and stones? Team Lay-Cool’s cutting words did more damage to James than a Singapore cane ever could. The former Divas Champion may have fought back, but Michelle and Layla’s bullying affected her so deeply that she was gone from WWE within months.

Mr. McMahon picks his poison

Like a true villain, Mr. McMahon would do anything for revenge, including hurting the things he loved the most (more on that later). Case in point, poisoning WWE with the New World Order in 2002 in order to kill the company he created. Like a petulant child who would rather break a toy than share it, The Chairman was so incensed over having to split control of WWE with Ric Flair that he brought in Hulk Hogan, Kevin Nash and Scott Hall to destroy the promotion just as they had done with World Championship Wrestling in the mid-90s. The plan ultimately failed (the trio weren't the same studs they used to be), but McMahon's madness was never so apparent.

Big Boss Man serves the food of the dogs

The Big Boss Man prepares a meal for Al Snow that ends up becoming a nightmare.

To find a bad guy as sinister as Big Boss Man, you’d have to leaf through the pages of a comic book. And not just any comic book, but one of those weird ones from the 1950s that the government banned. Think we’re exaggerating? Then you must’ve forgotten the time in the summer of 1999 when the enforcer from Cobb County, Georgia kidnapped Al Snow’s beloved dog Pepper, killed it, cooked it and fed it to him. Yes, that really happened. Part of the blame here has to go to Snow for actually eating the dish, but Boss Man can't be forgiven for turning SmackDown into "Tales from the Crypt."

JBL crosses the borderline

There are bad guys the WWE Universe loves to hate, and bad guys they just plain hate. JBL falls into the latter category. A snide, unapologetic bully who beat-up Hornswoggle and once drove a car into John Cena, the grinning Texan was never as despicable as he was in 2004. Locked in a bitter rivalry with the legendary Eddie Guerrero, JBL set his sights on his rival’s heritage and ran down Mexican immigrants to the point that he actually went to the Texas border to chase away a family crossing into the United States.

Andre makes a giant statement

How would Andre the Giant be remembered today if he hadn’t sided with Bobby “The Brain” Heenan against Hulk Hogan in 1987? The lovable oaf from Princess Bride? Probably. Sports-entertainment’s one true giant? Probably not. Had The Eighth Wonder of the World not turned his back on his friends and his fans in pursuit of the WWE Championship, there would have been no WrestleMania III, no 93,173 fans jammed into the Pontiac Silverdome, no WWE Title one year later. The Giant betraying the WWE Universe may have been reprehensible, but it's what truly made Andre a legend.

King Kong Bundy causes big trouble

Standing 6-foot-4 and weighing 450 pounds, King Kong Bundy had a hard time picking on somebody his own size. What was he going to push around? A Buick? But the man Gorilla Monsoon dubbed “a walking condominium” proved he was as spineless as he was big when he ambushed famed midget wrestler Little Beaver at WrestleMania III. Dropping all of his girth on the 60-pound man, Bundy nearly ended Beaver’s life that night and cemented his reputation as WWE’s biggest scumbag.  

Hart family drama

Symbolism turned stipulation at Survivor Series 1994, where Bret Hart defended the WWE Title against Bob Backlund in a submission bout in which winning required a ringside representative to throw in the towel. Tainting the contest was The "Hit Man's" splenetic sibling Owen, who manipulated his own mother to not only cost his big brother the championship but injure him at the hands of the crazed challenger. Backlund locked in a crossface chicken wing for minutes that felt more like hours while Owen shed feigned tears, emoting a faked concern that compelled Helen Hart to toss in Bret's unguarded towel. Instantly, the youngest Hart son celebrated, snaring his brother's loss-signaling cloth which Owen proudly toted long after - like a championship, meriting his most infamous deceit.

The Million Dollar Man makes a technical foul

The Million Dollar Man & Virgil find a way to cheat an innocent child out of $500.

At his worst, The Million Dollar Man could be as cartoonishly evil as Scrooge McDuck or Mr. Burns from The Simpsons. So much so, it's almost surprising there isn't footage of the wealthy Superstar taking candy from a baby. He came close enough in 1988, though, when he plucked a young boy out of the audience and offered him $500 bucks if he could dribble a basketball 15 times in a row. The crowd smelled a rat the minute the deal was made, but the kid still went ahead with it, bouncing the ball 14 times before The Million Dollar Man stuck his boot out and sent the ball flying. Unrepentant, the WWE Hall of Famer left the defeated child with this: “When you don’t do the job right, you don’t get paid.”

"Stone Cold" Steve Austin gets rundown

"Stone Cold" Steve Austin’s time at the top of WWE from 1997 to ’99 was the greatest run in sports-entertainment history. It came to an end at the 1999 Survivor Series. Mere hours before The Texas Rattlesnake was scheduled to battle Triple H and The Rock in a Triple Threat Match, he was run down by a car in the bowels of Detroit’s Joe Louis Arena. The shocking incident lost much of its impact as the mystery unraveled — first it was blamed on Rikishi who claimed he did it for The Rock, later it was revealed that Triple H was the mastermind behind the whole thing — but the nine months Austin spent incapacitated forever changed WWE.

J.R. gets barbecued

From being brutalized by the 350-pound Mankind to having his ankle damn near torn off by Jack Swagger, Jim Ross has survived more than a few attacks in his long career in sports-entertainment. But Good Ol' J.R.’s most horrifying run-in with a Superstar came in 2003 when he was set on fire by the monstrous Kane. As mentally unstable as ever after being forced to unmask, The Big Red Monster became unhinged in the middle of an interview with J.R. and began to shout, “You need to feel my pain!” The maniac then threw Ross on the floor, covered him in gasoline and dropped a lit match on his back. The ensuing terror of the WWE Hall of Famer burning in flames was so disturbing, it has rarely been seen since.

Big Show's grave injustice

Yes, Big Boss Man actually did something worse than butcher a man's dog and feed it to him. In a moment that should have qualified the maniacal Superstar for some serious psychiatric care, Boss Man crashed the funeral of Big Show’s recently deceased father and did the unthinkable. Inexplicably driving the same car from the “Blues Brothers” movie, the lawman interrupted the giant’s eulogy for his dad, hit him with a car, then hooked a rig to the casket and drove away with it. Horrified at what was happening, The World’s Largest Athlete instinctively leapt on the coffin and was dragged across the cemetery before tumbling off. What Boss Man did with the corpse after that was unclear, but it left everyone in the WWE Universe to wonder: “What the hell is wrong with that guy?”

The Nexus delivers a Raw deal

June 7, 2010 might have been Viewer’s Choice Night on Raw, but the show’s destiny ultimately fell into the hands of a vicious band of former NXT Rookies known as The Nexus. Led by Wade Barrett, the rogues emerged at the end of the night, storming the ring and decimating then-WWE Champion John Cena. Not content with merely dismantling The Champ, The Nexus laid waste to everyone and everything in its path, including the ring itself. The attack served as a chilling sign of things to come on Monday nights, as the faction would terrorize Raw for months.

Zach Gowen's bad chair day

People wanted to like Brock Lesnar. He was big, he was charismatic, he rarely lost. But for some reason, The Next Big Thing wasn't interested in adulation. He made that perfectly clear in 2003 when he grabbed the wheelchair-bound Zach Gowen — a young WWE fan who lost his leg to cancer as a child — and threw him down a flight of concrete stairs. If that wasn’t heinous enough, Lesnar actually laughed while he did it. The act was so monstrous, even the unflappable Mr. McMahon seemed disturbed by it.

The Million Dollar Man proves he's filthy rich

They say money can’t buy happiness — but it can get you a lot of other things. Just ask The Million Dollar Man. In his time as WWE’s most despised villain, the mega-rich rogue bought luxury cars, fancy furs — heck, he even purchased actual people. But the wealthy Superstar’s most dastardly dealing came in the winter of 1988 when he paid cash money for the WWE Championship. Striking a deal with Andre the Giant, The Million Dollar Man orchestrated a scheme to wrestle away Hulk Hogan’s coveted title that was so complex that he actually paid a man to have plastic surgery in order to look like referee Earl Hebner. Crime doesn't always pay, though. The scam quickly unraveled and The Million Dollar Man never went on record as champion.

Mankind goes to hell and back

The horrifying sight of The Undertaker throwing Mankind off the top of the 16-foot high Hell in a Cell structure at the 1998 King of the Ring may have been the defining moments of WWE’s Attitude Era. It was brutal, but the fact of the matter is what came later was even more devastating. After paramedics attempted to take Mankind away from the ring, the madman broke away from their grasps and climbed back up to the top of the cage, busted shoulder and all. The Deadman, showing no mercy for his battered opponent, immediately grabbed him by the throat and chokeslammed him through the ceiling of the structure. The impact was so vicious, it knocked Mankind out and sent his tooth through his lip and into his nostril.

Earthquake squashes Damien

“Mean” Gene Okerlund called it one of the most appalling incidents he ever witnessed, and with good reason. In 1991, the massive Earthquake used his enormous 460-pound frame to squash Jake Roberts’ python Damien in the center of the ring. Roberts, who had been tied up in the ropes by the Canadian behemoth, had no choice but to watch his snake crushed to death before his eyes. Few Superstars were better at the psychological game than Jake Roberts, but that incident would forever disturb The Snake.

Stephanie McMahon feels The Viper's kiss

Name a Superstar more vicious than Randy Orton in the early part of 2009. Piper in the '80s? Triple H in 2000? You can argue both, but few villains can match the campaign of terror The Viper waged against The Game and the McMahons at the end of the decade. Hellbent on destroying Triple H before their encounter at The 25th Anniversary of WrestleMania, Orton targeted the man's family, punting his father-in-law in the head before DDTing his wife in front of his eyes and then kissing her face. The Viper hasn't been as vicious since, but every opponent now knows what he's capable of.

CM Punk crashes the party

This was CM Punk at his most depraved. Disheveled, unhinged and flanked by the dead-eyed zombies in his Straight Edge Society, the soulless Superstar crashed a celebration for Rey Mysterio’s daughter on SmackDown in 2010. Knowing that Mysterio would have no choice but to stay by the side of his wife and children, Punk took his time as he slinked across the ring and warbled his way through a haunting rendition of the “Happy Birthday” song. There was no physical aggression here, but there didn't need to be. Punk embarrassed Rey in front of his family — a humiliation more painful than any bare-knuckle beating.

Jimmy Snuka gets creamed by a coconut

In the nearly 30-years that have passed since “Rowdy” Roddy Piper smashed a coconut over Jimmy Snuka’s head on “Piper’s Pit,” the shocking act has become the stuff of parody. Hell, Hot Rod even reenacted the stunt on Zack Ryder’s spiked hair at WrestleMania XVII. But don’t' let the parodies fool you. When Piper cleaned Snuka's clock in 1983, it was as nasty as it gets. Treating one of WWE's best loved Superstars like an animal, The Rowdy One knocked his rival out with “the coconut shot heard round the world” before shoving a handful of bananas in his mouth. Mania like this would shock the WWE Universe, but earn Piper distinction as one of WWE’s most unpredictable legends.

Matt Hardy is a victim of love

WWE has been likened to a soap opera for years, but that comparison was never as apt as it was when a real life love triangle spilled from the locker room into the ring in 2005. Once WWE’s most popular couple, Matt Hardy & Lita’s relationship came to a shocking end when the former WWE Tag Team Champion discovered his girlfriend had been cheating on him with his one-time rival, Edge. Obviously shredded, Hardy went to war with The Rated-R Superstar, but the jilted lover’s rage barely mattered. Lita & Edge were unapologetic about their adultery and saw to it that Matt’s life and career were torn apart.

The Undertaker takes a bride

Thirsting for power in the spring of 1999, The Undertaker and his Ministry of Darkness descended upon WWE like a heavy fog blanketing a cemetery and few were quite as terrified by The Phenom’s evil intentions as Mr. McMahon’s daughter, Stephanie. Following a “higher power,” The Deadman and his minions stalked The Chairman’s child for weeks before abducting her, lashing her to an ominous Undertaker symbol and forcing her to participate in a twisted wedding ceremony on Raw. Despite his combative relationship with her father, “Stone Cold” Steve Austin ultimately rescued Stephanie from a cruel fate as The Undertaker’s bride, but Mr. McMahon’s little girl was never quite the same.

Shawn Michaels cuts Marty Jannety out

What is it about the dissolution of The Rockers that has made it the most iconic breakup in tag team history? Was it the way Shawn Michaels ruthlessly drove Marty Jannety’s head through the plate glass window of Brutus Beefcake’s “Barber Shop” talk show set? Was it the way HBK's cowboy boot cracked so perfectly against his partner’s chin? Nah. In truth, it was the way Shawn Michaels went on to become arguably the greatest Superstar ever to compete in WWE, while his old friend was left behind to become a punchline. Say what you will about survival of the fittest, but it doesn’t get much bleaker than this.

Jake Roberts sinks his teeth into Randy Savage

Besides that Tuxedo Match that ended with Howard Finkel in his underwear, there isn’t much footage in the WWE archives that is more unsettling than this. In Fort Wayne, Ind., in October of 1991, Jake “The Snake” Roberts attacked a helpless Randy Savage with a dangerous cobra, forcing the serpent to sink its fangs into his rival's arm. Raw and visceral, the carnage would disturb any viewer, but watch Roberts. As pandemonium ensues with EMTs rushing the ring and children in the audience bursting into tears, Jake stays calm and repeatedly slaps Savage’s face like a predator toying with its prey. The smacks aren't meant to harm Macho Man, just remind him that Roberts has him right where he wants him. Cold blooded indeed.

Mr. McMahon screws Bret

Fourteen years later and we’re still disgusted by the events that concluded the 1997 Survivor Series. Why? Because, in the end, the bad guy won. After screwing Bret Hart out of the WWE Title in the champion's home country, Mr. McMahon didn’t suffer. Instead, he parlayed his new-found infamy into literally a billion dollars worth of success. Hart, on the other hand, went down to WCW where he was criminally misused before a concussion brought a premature end to his legendary career. In the years since, "Hit Man" has come to terms with what happened that night — he even got a chance to pound The Chairman at WrestleMania XXVI — but nothing can change the fact that he was the victim in the lowest moment in the history of sports-entertainment.

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