Wearing the Black Hat: The Most Entertainingly Evil Acts in WWE History

This might not be something that the WWE wants to hear as they continually push John Cena as the unflappable "good guy" who will never fail in his battles, but as we grow older there is something about the concept of evil that fascinates and even entertains us.

Part of this I imagine is because we are all inherently good people at heart (I'm an optimist), and so we know that there are certain lines of societal rule that you simply don't cross. And no one really wants to cross those lines in the first place. And when there are people who do cross those lines, well, we rightly condemn them as not indicative of society as a whole. If we were all petty foul creatures at heart, I seriously doubt we'd still be around as a species long enough to develop a medium where I can blab about finishing moves and be wildly entertained by the creative comments section below (especially when I'm an idiot and initially forget to even mention the Figure Four).

…But for some reason the realm of professional wrestling doesn't quite play by the same rules as the rest of the real world. Because there are only so many ways that "bad guys" can express how eeeeevil they really are, it falls on the heel to get creative. After all, they're not getting over because of how much the fans like them, but in how low they will stoop just to piss us off. Take this for example.

Everything about this moment is *supposed* to be awful. Randy Orton, the established company heel, is currently in the middle of beating up Daniel (YES!) Bryan, when some fan desperately shouts for the ref to ring the bell to disqualify Orton. Except Orton pauses, directly addresses the fan in full view of the camera, and then proceeds to taunt the poor bastard while smoothly transitioning into a suplex onto the announce table and crushing our poor hero. That moment, at its core, is supposed to make us hate Randy Orton and pay money to see his ass get kicked. (Which plenty of people did for WrestleMania 30.)

…Yet there's a small and objectively terrible part of each of us that probably found this moment really entertaining.

There's a lot of debate going on these days about what the role of a heel should be in today's WWE, especially in the wake of Jim Ross' comments on the subject, but in the meantime I'd like to propose another angle. After spending far too much time traipsing around the WWE Network and the rest of the internet, I've compiled a list of my personal top five moments where a heel stopped being just a jerk and became an entertaining jerk. And because I understand that's a pretty subjective topic to tackle, I will include a short breakdown as to why the moment is entertaining.

As always, just because I say something is entertainingly evil, doesn't necessarily mean that what you think is entertainingly evil is objectively worse than what I've written. After all, why on earth discourage the creativity and opinions to be had in the Cagesider Comment Section?

Let's begin!


Seeing as I'm late to the game in being a wrestling fan, whenever the topic of nWo comes up I run into…a lot of opinions. The primary opinions about the gimmick seem to be thus:

1.) In the beginning? WHITE-HOT.

2.) As time drew on, less entertaining and more obviously a way for Hulk Hogan and his buddies to hog the spotlight. (Though I've found that apparently the nWo Wolfpack gimmick was pretty over at the time of its run…until the Fingerpoke, that is.)

Thankfully, this is a moment that occurred early on in the formation of the nWo, when they didn't take up the majority of the WCW roster and it was mostly Kevin Nash and Scott Hall stirring shit up.


It's hard to picture now, when we live in an age where "Kayfabe" no longer means anything close to what it used to, but when Nash and Hall were screwing with WCW in the early days of the nWo, it was absolutely gripping television. As you can tell from the background noise on that clip, the crowd wasn't really reacting because they had no idea what was going on. This was something unlike anything they'd seen before. And that small, objectively terrible part of us can't help but chuckle at simply how blatant Kevin Nash is. For God's sake, this is like that Casey Heynes video in reverse: instead of a kid realizing that he is larger than the puny twerp bullying him and that it is time to remind the world of that fact, here's a genetic freak taking on a guy that looks like, well, a lawn dart, in his hands and then throwing him right into the side of a truck. THUMP. It's like the absolute worst escapist fantasy you could think of if you were momentarily given the powers of the Hulk: instead of using your power to smash things for good, you'd just be smashing everyone who wronged you for the pettiest of reasons. Speaking of petty...


Chris Jericho is a comic gold mine. I could write an entire book on his greatest hits, but right now I wanna focus on his little feud with Dean Malenko. (Partially because it's wildly entertaining, and partially as an apology for forgetting the Texas Cloverleaf in my last article.)

On March 15, 1998, Malenko failed to beat Jericho for the WCW Cruiserweight title, and then announced to interviewer "Mean" Gene Okerlund that he was going home. This would probably have made him the heel in the situation, but Jericho decided to run with the idea of being perhaps the greatest douchebag champion in the history of anything.


Jericho did this shit for months, taking it far past the standard "dismiss your challenger as a whiny baby sort" that Cena tends to use if he feels threatened and directly into "I am secretly terrified of this man who nearly took my belt so I must remind the world of his inadequacies at every possible moment" territory. This is the period of time that Jericho gave us promos like the one above, and you're crazy if you think I'm not including a link to the legendary "Man of 1004 Holds" promo as well. This is so disproportionate, so needlessly self-aggrandizing, that it stops being the work of a man you despise and becomes that of a man you love to despise. (Oh, by the way, Dean Malenko got around to kicking the shit out of Jericho at WCW Slamboree on May 17, 1997.)


Much like Chris Jericho, Randy Orton could probably get himself a couple of lists on his lonesome considering all of the crazy stuff he's done. He's not even close to 40 yet, and he's been around the company for years. You'd think that people would learn to stay away from a man who does stuff like this, but evidently they never learn. Which brings us to this next moment.

It takes place during an incredibly bitter feud between Randy and Triple H. Though there were obviously several years separation, one can probably say that Randy's exile from Evolution (not that one. This one.) led to the increasing hostility between the two, with Randy going after not just Triple H but his extended family. And by extended family I mean of course you know who I mean. Orton punted Shane and Vince McMahon, and with the help of his little stable Legacy (Ted DiBiase Jr. and Cody Rhodes), managed to get Triple H handcuffed and helpless at the corner of the ring, leaving Stephanie McMahon completely defenseless...


Let's get something straight here. In real life, anyone who has the gall and/or lack of morals to do to Stephanie McMahon what Randy Orton did to her deserves to take an unprotected gore from Rhyno…at the very least. If you are built like a prototypical super soldier you'd see in one of the Halo games (or perhaps that sick-looking Destiny game that Bungie is releasing later this year), then you have a responsibility to understand that you can seriously hurt people if you aren't careful. And if you know this and don't care about it, well...

But this is professional wrestling. And this involves the McMahon family.

Remember, this is a few years removed from the infamous "Reign of Terror" where Triple H and Stephanie ran roughshod over the company (no, not this one. The other one. The one in the Attitude Era. No, the other one.), either kicking peoples' asses (Haitch) or firing their asses (Stephanie). For the record, I still haven't forgiven Trips completely for firing my boy Mick Foley after that hellacious cage spot. But that's neither here nor there.

My point? Despite the WWE understandably operating under the "kids don't have the attention span to pay attention to continuity going back several years" mindset, there were a lot of people who remembered every little thing that Stephanie and Trips had done over the years, and this was also a few years after the closing down of WWE's ECW brand, which effectively turned WWE into the monopoly it is today. So, sick and twisted as Randy Orton was acting (and admit it, you know he plays an excellent unhinged heel when they let him), that small and objectively terrible part in all of us was fighting back a smirk when Randy spike-DDT'd Stephanie onto the mat. Not even the legitimately awesome revenge Triple H got could keep us from chuckling at the shot Randy'd gotten in.


See, this one is tricky. Because when you talk about Jake Roberts' feud with the Macho Man (Oh Yeeeeeah!), you kind of have to talk about these two events in tandem. This event I'm writing about, and the other more infamous one. Yet I'm only going to talk about this event, because of a simple reason.

I didn't find Jake Roberts having that fucking king cobra biting Randy Savage entertaining. I legitimately found it scary.

But I digress.

Before THAT happened, there was the wedding of Randy Savage and Miss Elizabeth. You know, for a desensitized smark like myself, seeing a relationship like this and how it was covered in the medium of professional wrestling is strangely nostalgic, even though it's kind of hokey. But it's a good hokey, the kind that puts a goofy smile to your face that you can't really explain but that you're glad to have. Put it this way, they can have a million on-screen weddings in WWE, but none of them will EVER top Randy Savage and Miss Elizabeth's wedding.

Which brings us to the opening of the wedding gifts, and in particular the one that Mr. Jake Roberts decided to send...


This one really becomes funny when you stop and think about just how many questions Jake had to ask himself in order to pull this off. Questions I imagine that went something along these lines: What kind of snake should I get? What would be the least suspicious wrapping paper and box to put it in? Which guard is stupid enough to accept a delivered gift from ME for a wedding and won't bother to check the contents? Do I dress the snake up in a little outfit just to mock them? And perhaps my personal favorite: How do I convince my buddy THE UNDERTAKER to play along with this?

You know. Logistics.


Let me start this off with a qualifier. Roddy Piper is, by all accounts, one of the friendliest and honest men in the history of the business. He also appears to be a devoted family man (who apparently drew mocking from some of the people in WCW because he wore his wedding ring even in the ring), and if you are a fan who happens to run into him at a convention or show, all reports indicate he'll respect your presence.

I say all of this because it is also true that Roddy Piper was (and is, really) one of the greatest heels in the history of the business. And this is probably his crowning achievement.


…HOW? How did they get away with this? Can you imagine a moment like this in today's WWE? Not only would the company immediately shoot the idea down, but if it somehow managed to leak through the backlash would be titanic. (Remember, this is the company that temporarily fired Daniel Bryan for choking Justin Roberts by his tie.)

And think about just how much research that Piper had to do in order to hit every single racially insensitive stereotype he possibly could in order to get under Jimmy "Superfly" Snuka's skin. Okay, I'm a moron, so I get the coconut and the pineapple, but the bananas schtick seems like it's mixing offensive stereotypes. Which in a way steers this back from jaw-droppingly racist and more into absurdist racism (which is really quite redundant when you think about it). It's less the horrifically casual racism displayed in 12 Years A Slave and more in the over-the-top ridiculous category like Leo DiCaprio's character's bullshit rant about phrenology in Django Unchained.

Thirdly, if rumors are true that Piper just ad-libbed all of his interviews, how did Snuka not just straight-up murder Piper? That is a terrific dedication to your craft, especially when the guy's just bashed your head in with a coconut and you took the set down with you.

Objectively, this is a terrible act. We would pay money to see Piper eat a Superfly Splash off of the top rope because of this. But that comes later. Right now, we're watching this moment and all we have are our current emotions. And while the better part of us will win out and will recognize the evilness of this act (and know that we would never do such a thing), hiding deep in the back of our head will be that objectively terrible part of us that's probably thinking...

So what do you think, Cagesiders? Did I miss any particularly entertaining evil acts, or do you think something was put in the wrong spot? Sound off in the comments below. I'm sure I'll return to the Art of the Finisher series in the future, but for now hope you enjoyed this one.


Once again (this is becoming a running gag, I think), this takes place during a CHIKARA match, with Incoherence tag-teaming against the Super Smash Brothers. But no one will remember the match itself, but rather the mind games Delirious played with Player Uno for the entirety of the thing. Just wait for the ultimate insult that he saves for the very end. Watch the whole thing from start to finish for the full effect.

The FanPosts are solely the subjective opinions of Cageside Seats readers and do not necessarily reflect the views of Cageside Seats editors or staff.