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Who Is The Greatest Wrestling Heel Of All-Time?


It was a crazy week in The Basement with Robbie Fox and I giving our thoughts on The Suicide Squad as well as the first episode of What If that spawned some hellacious Barstool What Ifs.

However my favorite trip to our underground podcast lair occurred when Loki writer Michael Waldron dropped in to talk old school wrestling while promoting his new TV show Heels that debuts on Starz tonight.

In full disclosure, I was a little skeptical about hopping on the pod with my close personal friend Michael when Robbie asked because I haven't cared about wrestling since I stopped watching almost 20 years ago, which is crazy to think about because I cherished the cartoonish 80s/90s WWF as a kid and was OBSESSED with the sexually charged violence of the Attitude Era WWE along with the more mature WCW and flat out crazy ECW. But Robbie said it wouldn't be a problem since we would just be having a casual discussion about wrestling among three fans and boy was he right discuss anything from this decade and mostly this century.

We talked about which heels we all grew up loving since they are the straw that stirs the drink in the grappling world (Waldron is closer in age to my old ass than our little baby fox Robbie), how moments like Hulk Hogan going Hollywood on WCW changed his perception of wrestling, and what it was like watching scrambled Pay-Per-Views back in the old days of cable.

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You know Waldron is a real one when he watched wrestling the way most of us watched the Spice Channel

But a good chunk of the pod was about our favorite heels growing up since they are the straw that stirs the drink in the grappling biz as well as the name of Waldron's newest project. So check out the video above at the top of the blog or listen on your favorite podcast site if you are an audiophile for some good wrestling talk along with some light ball washing for Waldron crushing Season 1 of Loki.

For the record, here are my 3 favorite heels:

3. Ric Flair

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I didn't pay much attention to WCW as a kid because I grew up North of the Mason-Dixon Line and had running water in my house. So a good chunk of Ric Flair's early heyday was lost upon me until he entered the WWF and became the biggest motherfucker in the Federation. I've seen plenty of heels pull the kind of cowardly stunts that Flair used to pull. But the way he did it after all the cocky swagger would drive me NUTS, which is the mark of a great heel, along with the unreal promos he used to cut.

For the record, @NoContextFlair is a Must Follow on Twitter

The thing however that made me go from disliking Ric Flair to hating him with every fiber of my being was when he tried to besmirch the good name of Miss Elizabeth.

Miss Elizabeth was the first crush of my life and at that point was the greatest woman on Earth outside of Mama Clem. So Flair going at her instantly made him my biggest enemy on the planet instantly. God damn that man was great at generating hate.

2. Vince McMahon

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Winning the silver medal is Vinnie Mac. Pretty much everything we loved about Stone Cold Steve Austin, which is a whoooooole lot of love, came from our hatred of Vince McMahon. The prick boss that does everything he can to keep the working man down in between outrageous rule bending and the most vicious dad voice yells you have ever heard. The fact he did all of it while running a company that ate all its biggest rivals is easily the most impressive thing I've seen in sports entertainment and the reason I know Barstool will indeed land on the moon since him and Portnoy are pretty much the same exact human.

1. Bobby "The Brain" Heenan

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I have no problem declaring the debate for GOAT heel as a two man race between Ric Flair and Vincent K. McMahon because they were the stars of the show but Bobby Heenan will forever be my favorite heel just because of the unbelievable dirty moves he pulled as a manager as well as the wittiness of the countless lines he dropped that completely flabbergasted Gorilla Monsoon as an announcer. 

Bobby The Brain was truly the king of the spinzone and for my money the best manager as well as best announcer to ever get in the wrestling game, which considering their importance to the show is no small feat. God damn I miss that dude.

There are PLENTY of other worthy heels on my list including Triple H, Chris Jericho, Rowdy Roddy Piper, The Rock, Macho Man, Mr. Perfect, and The Million Dollar Man to name a few. God dammit do I love and miss wrestling. We really need another Golden Era to jump off soon now that I have kids who are old enough to understand what's going on so I can use them as an excuse to go to live events and buy shirts that nobody my age should be buying.