The Magnificent Seven: The Top 7 Most Heelish Acts in Pro Wrestling

In the modern era, WWE has insisted that face-heel designations are unimportant relative to fans choosing who and what they wish to get behind. Call me old fashioned, but I maintain that the face-heel divide is the number one fundamental drawing card in professional wrestling. Yes, we fans pay money to support our favorites, but we also shell out to see the characters we despise get their comeuppance in the form of physical punishment, injury, and humiliation—such is the nature of the pro wrestling business. And contrary to the moral ambiguity of cheering while someone gets hurt in the UFC Octagon or when a hated professional athlete is legitimately hurt, in pro wrestling we know that we are taking in a story–that watching Triple H scream in pain and tap the mat is not an indication that another human being is actually broken, but rather a dramatic representation of the same phenomenon.

But what makes us hate heels? Cheating, betrayal, bullying, vicious attacks—these are all pieces of the puzzle. Taking into consideration the full history of wrestling, it’s nearly impossible to narrow a list to just seven of the most heelish acts, but here I present my best effort to capture seven particularly nefarious moments that drew heat, captured the imagination, and, as the saying goes, most made us want to cheer the good guys and boo the bad guys.

#7. Big Show Swings the Rey Mysterio Into a Ringpost at Backlash 2003

While Kevin Nash lawndarting Rey Mysterio in a parking lot back in WCW may be more iconic, there’s something particularly devilish about Big Show’s post-match attack on Rey Mysterio at Backlash 2003 that has always stuck with me. The moment came in the aftermath of a Show-Mysterio match that Show– obviously the much bigger man–won handily. Rather than leaving his badly beaten foe to be carried out of the arena, Show went one step further as a bully, a jerk, and a vicious son of a gun when he lifted Mysterio and the stretcher and swung them like a baseball bat into the ring post—an awesome demonstration of his power, a sick visual, and all the more brutal for Mysterio landing head first at ringside.

#6. The Road Warriors Go After Dusty Rhodes’s Eye in 1988

The Road Warriors are an underrated case of natural bad guys who were too cool for the fans to boo. Time and again they came in as some of the most intimidating villains on the block, only to turn face when the fans couldn’t resist cheering them. In 1988, the NWA made a new effort at turning them heel and did all that they reasonably could, between the duo destroying tag partner Sting to start the turn, and then launching this particularly vile attack against Dusty Rhodes. Three years after Magnum TA threatened Tully Blanchard’s eye with a spike in their iconic I Quit match, The Road Warriors removed a spike from their signature shoulder pads and, with minimal provocation, made their best effort to blind The American Dream.

The incident was purportedly an act of rebellion on the part of Rhodes after TBS warned him to tone down the violence, and it led to him leaving the promotion. Regardless, it served up an unforgettable bit of graphic villainy in the annals of pro wrestling.

#5. The Sandman Feigns Blindness

The Sandman was one of ECW’s most iconic performers, and in one of his most memorable angles, Tommy Dreamer knocked a lit cigarette into his eye, apparently blinding him. The angle set a number of pieces in motion—Sandman became a martyr, Woman bolstered her heel cred by turning on Sandman and blaming him for his own incapacitation, Dreamer became more of a hero for defending Sandman and dedicating his career to him. This all led to an elaborate retirement ceremony for Sandman, which culminated in him heeling on Tommy Dreamer in a vicious attack.

In an era on the cusp of Attitude and NWO domination, ECW flirted with the line between reality and sports entertainment, and managed to dupe a portion of its smark audience into believing Sandman was legitimately blinded (to his credit, he reportedly played blind in his real life, well outside the arena during that period), and those who weren’t fooled nonetheless bought into it being a captivating wrestling angle. The ensuing revelation that he had been faking the whole time, and that he would attack Dreamer after he had stood up for him was positively dastardly, and a masterful heel move.

#4. Andre the Giant Rips Off Hulk Hogan’s Cross

The wrestling world has seen far more hellacious and violent heel turns than that of Andre the Giant, such as Shawn Michaels throwing Marty Jannetty through a plate glass window or Terry Funk piledriving Ric Flair through a table. But when you’re as massive as Andre the Giant—both in terms of physical size and star wattage, everything you do feels a bit bigger. When the WWF presented trophies to world champ Hulk Hogan and the undefeated Andre the Giant, the big guy left in a huff, resentful that The Hulkster was showing him up. The next time we saw him, the stage was Piper’s Pit and Andre came out to challenge Hogan to the biggest wrestling confrontation of all-time—a one-on-one bout to main event WrestleMania 3. This was no friendly challenge, though, but rather tantamount to a pro wrestling death threat when Andre came with his new manager, arch-heel mastermind Bobby Heenan, in tow, and proceeded to tear Hogan shirt and, most powerfully, the crucifix from his neck, drawing blood from Hogan’s chest. For over a year and a half to follow Hogan and Andre would engage in a feud that may not have produced any particularly good matches from a purist’s perspective, but nevertheless carried with them an atmosphere of magnitude—big-time matches between two larger than life personas, each of whom was masterful at bending a crowd to his whims. It all started when Andre rejected the fans, Hogan, and, symbolically, God himself to start his lone big-time US heel run.

#3. Hollywood Hogan Turns on WCW

In the scheme of big heel turns and massively heelish acts, this entry, like the one before it on this countdown, wasn’t particularly violent or dramatic in a vacuum. Given the full context, however, and the crowd reaction, I don’t think there’s much argument against it having been one of the greatest turns of all time and a truly special moment in the history of heeldom.

The fledgling NWO—before it was even known as such–was one of the hottest heel acts ever in wrestling, with Scott Hall and Kevin Nash running roughshod over WCW. Things looked like they would come to a head at Bash at the Beach 1996 when Sting, Lex Luger, and Randy Savage were pitted against The Outsiders and a mystery partner. The mystery man didn’t show up at the opening bell, and thus it looked as though WCW’s three-on-two man advantage might play in their favor. Then Luger got knocked out cold, evening up the sides. In the late stages of the encounter Hall and Nash had control and Hulk Hogan emerged from the dressing room, seemingly to fill in for Luger—only to drop arguably the most iconic leg drop of all time on Savage (the closest runner up would be Hogan leg dropping The Iron Sheik to win his first world title). Reality set in and the match ended not in a pinfall, submission, DQ, or countout, but rather a meltdown of nuclear heat on the part of the live crowd as the fans realized that wrestling’s greatest hero had just gone bad. Hogan proceeded to cut the first of what would be many, many lengthy heel promos, which led to the audience literally throwing garbage in the ring and booing its hearts out—a simply phenomenal reaction to a spectacular heel moment.

#2. The Horsemen Make a Hit on Dusty Rhodes

In 1986, in the early days of the Four Horsemen, the concept of the heel stable was still a new one, and the principle of a group of bad guys teaming up to beat up a face was a huge heat-getter. As such, The Horsemen did something truly iconic when they hopped in a car, video taped themselves following Dusty Rhodes and eventually beating the holy hell out of him in the parking lot of Jim Crockett Promotions. The grainy, shaky footage added to the gruff realism of the moment, and the NWA was wise to promote the moment not as live action (often a dead giveaway as to how contrived moments are in pro wrestling) but rather as footage that was self-recorded outside the confines of a wrestling show or a wrestling arena—dastardly documentation of a heinous attack on one of wrestling’s great heroes of the era. The attack culminates with Rhodes tied to a truck, The Horsemen surrounding him, talking trash, choking him, and ultimately breaking his arm with a baseball bat.

In the spectacular world of professional wrestling, sometimes the most memorable moments are those that run contrary to convention. Moments thatrather are gritty and ugly—that are not so much escapist as legitimately difficult to watch. As heel moments go, this one played that particular dynamic to perfection.

#1. Jake Roberts Threatens Miss Elizabeth

I was late in my elementary school career and coming of age as a wrestling fan when Randy Savage and Miss Elizabeth engaged in “The Match Made in Heaven”—getting hitched at SummerSlam 1991. The moment felt like a perfect capstone to a perfect love story. Savage had retired following a classic match with The Ultimate Warrior at WrestleMania 7, and made one last turn for good, reunited with beautiful Miss Elizabeth to seemingly ride into the sunset. In unprecedented fashion, their nuptials went off without a hitch and got the main event spot at a major PPV.

All seemed well when, after the show, Savage and Elizabeth opened gifts at their reception—only for one box to contain a king cobra. A moment later, The Undertaker had KOed Savage with an urn and Roberts was backing Elizabeth into a corner with his snake. In threatening the WWF’s ultimate damsel in distress, Roberts became the WWF’s ultimate villain, the encore to which came when he sicced the cobra on Savage too, tying up The Macho Man in the ropes for the snake to sink its fangs into his arm in front of a live audience weeks later. In a still-very-cartoonish WWF landscape, Roberts injected a sense of darkness and real danger that foretold a less family friendly product to develop years later.

What are your picks for wrestling’s most wicked heel moments? Let us know in the comments section.

Read stories and miscellaneous criticism from Mike Chin at his website and his thoughts on a cappella music at The A Cappella Blog. Follow him on Twitter @miketchin.