Those are the best kinds of heels, generally - the scummiest of the scummy, the most reprehensible fiends that have ever graced WWE's TV cameras. Their villainous exploits are generally so memorable that years after the fact, we can recall how they made us feel. And how they made us feel is definitely a subjective thing.
For this list, there will be both moments that I found to be truly riveting in their ghoulishness, while others received a less-than-optimum reaction, perhaps being a little too silly or demented to have the desired effect. And those can be debated until the end of time, because how something makes you feel is, again, subjective. But there's no denying that the actions on this forthcoming list were truly carried out by certified creeps.
10. Rick Rude Pays "Tribute" To Cheryl Roberts (1988)
Ravishing Rick Rude was a womanizer of the highest order, believing himself to be entitled to whatever sleek, vibrant gal that he so desired. He would handpick women from the crowd to give a passionate smooch to, and didn't take kindly to refusal. That was the case when one selected woman turned down his offer, revealing herself to be Cheryl Roberts, wife of Jake "The Snake".
Rude and Roberts warred throughout the summer and fall of 1988, but it was in a match against Junkyard Dog at that year's SummerSlam that Rude unleashed a truly devious work of art. Known for his customized airbrushed tights, Rude dropped the waistline of his during the match, revealing a second pair underneath - with Cheryl's face emblazoned on both the crotch and backside. Rude swivelled away suggestively, and it took only three seconds for an irate Jake to hit the ring in an attempt to kill him.
9. Jake Roberts Makes It Personal (1991)
But Roberts was no saint himself (now *there's* an understatement). In 1991, Roberts turned heel and entered into an extremely-intense feud with a then-retired Randy Savage. The most visceral image of the entire rivalry came shortly before Survivor Series, when Roberts snared Savage in the ring ropes, and sic'ed a cobra onto Macho Man. It quite literally bit into Savage's arm.
Depending on your point of view, that may have been mere child's play compared to the post-match fracas at This Tuesday in Texas when Roberts DDT'd a victorious Savage several times, before threatening another snake attack. Miss Elizabeth tearfully pleaded while shielding Savage, which only seemed to stir twisted feelings inside of Roberts. Then, to everyone's horror, Roberts smacked Liz across the face before departing. His promo after the fact, in which he veered into sexual lust, was both gripping and disgusting at once.
8. Kane's Family Reunion (1998)
In the dark and twisted realm of Kane and The Undertaker, all things are possible, many of them absurd. There were seemingly no limits to a feud so macabre that it made Fangoria look like Highlights for Children. Fire was a recurring item within the rivalry, as a casket with Undertaker inside was set ablaze, while a random crew member was also scorched by a sadistic Kane.
But the kicker had to be the time that Kane brought the caskets containing he and Undertaker's dead, charbroiled parents out on Raw is War. You know you're watching professional wrestling when a man can watch his father's casket be immolated, before being Chokeslammed into his mother's coffin...by his little half-brother. Just makes me miss the Attitude Era even more.
7. Big Boss Man's Drive By (1999)
What is it with this company and caskets? Incredibly, the most bats**t-crazy angle involving a casket didn't include The Undertaker. Instead, it involved the man he once left to die in the desert (Big Show) and a man he once lynched for a lark (Big Boss Man), and if you didn't laugh at least three times watching this angle, you're a liar.
But yeah, Boss Man was pretty scummy, crashing the funeral of Big Show's father while driving the Bluesmobile, running over Big Show, hooking up the casket to the back of the car with a chain, and then driving off with it. The sight of Big Show body-surfing the casket in an attempt to prevent Boss Man from, you know, stealing his dad's corpse, would've been a viral video had it been released in the social media age. This would've made Boss Man the most disgusting heel ever if people weren't so busy cracking up at the footage.
6. Vince Humiliates Trish (2001)
Okay, this was much less funny, unless you count Paul Heyman's immortal did-he-just-say-that line about getting to see a certain sitting President while in DC. Ultimately, Vince would get his in Trish's presence several times over (her smacking him at WrestleMania, her being present when Vince was shoved into Rikishi's ass, etc), but this is one of those bits that just didn't wash, even 17 years later.
It started awkwardly enough when a vulnerable Trish attempted to do anything to earn forgiveness from Vince at his most repulsive. This included barking like a dog while on all fours, and being made to take her clothes off against her will. The Attitude Era pushed the envelope in a multitude of ways, but this was one that felt truly uneasy, no matter how much comeuppance Vince would ultimately get.
5. Ciampa Takes A Ring Off It (2018)
The supreme villain in today's wrestling world is Tommaso Ciampa, who works harder to be an asshole than Tiger Woods did to regain his championship golf form. In the entire feud with former friend Johnny Gargano, you couldn't ask for a more likeable hero and a more detestable fiend across from him. Of the many awful things that Ciampa has callously done to Gargano.
It was almost beautiful, the heinousness of Ciampa removing Gargano's wedding ring, then spitting on it, before flinging it deep into the crowd at NXT TakeOver: Chicago this past June. Any heel whose entire existence hinges on, "What can I do today to be more disgusting than I was yesterday?" is an automatic winner. And his Twitter is eviler, and thus better, than yours.
4. The Screwing Of Katie Vick (2002)
I guess the intent was that we were supposed to go, "Man, Triple H is a dick!" Instead, we were too busy cursing those with creative authority that greenlit this regrettable segment. Even Triple H, years later on the Opie and Anthony Show, admitted that the whole experience was "mortifying". What began with your usual garden-variety accusation of murder spiralled into something much, much worse than murder.
Triple H filmed a vignette that was supposed to be "found footage" of departed cheerleader Katie Vick (girlfriend of a certain future politician) lying in a casket, while Helmsley played Kane (mask and all). Then Triple H got undressed and proceeded to simulate sex with the lifeless baton-twirler, rhythmically doing the coffin conga with her until he "screwed her brains out". Well, say this much - it was definitely not something a babyface would do.
3. Orton Steals A Kiss (2009)
Finally, something far less cartoonish. Randy Orton was in his element as a slimewad in early 2009, justifying his assaults on the McMahon family through a diagnosis of intermittent explosive disorder. When he laid his hands on Stephanie several weeks before WrestleMania XXV, there seemed to be far more control to his actions, and his eyes showed he knew exactly what he was doing.
While Triple H was handcuffed to the ropes, he could only watch as Orton DDT'd his wife to the canvas, before placing a small kiss on her face, his eyes locked on the infuriated eyes of helpless WWE Champion. It's moments like this where you truly want the babyface to get revenge, and had the 'Mania match been an Eli Roth-esque bloodbath, it'd have been cathartic.
2. Punk Urns Undertaker's Ire (2013)
It's hard to call it "divine intervention" whenever anybody dies, but the sad death of William "Paul Bearer" Moody in March 2013 would add a wrinkle to CM Punk's forthcoming WrestleMania match with The Undertaker. Lacking a fundamental angle for the match, WWE invoked the death of Moody by having Punk abscond with Bearer's urn, as part of the mind games.
Punk made a point to disrespect the urn as much as possible, tossing it to himself like a football, dropping it onto the floor, and even dumping the contents of the urn all over Undertaker during a beatdown the week before WrestleMania. Some interpreted the ashes inside to be those of Bearer's, which only fanned the flames of those wanting Undertaker to score ultimate revenge.
1. Sara Has A Stalker (2001)
This one could have been paid off a little bit better. So somebody had been secretly videotaping Undertaker's wife Sara during private moments, narrating the footage through a distorted voice. The stalker was later revealed to be Diamond Dallas Page, part of the early wave of WCW invaders. Turned out that he had his eye on making The Undertaker go crazy.
The angle was really ineffective, on account of Page generally getting his ass handed to him by 'Taker on the regular. Also, they couldn't decide if DDP's actions were just "mind games" to screw with Undertaker, or were part of an unrequited obsession with Sara (as evidenced by a candlelit shrine he had created of her). Most would've guessed the former, since Page was then married to a genuine bombshell in Kimberly, after all.