20 Most Hated Heel Moves In Wrestling History

Significantly underrated on the mic and in the ring, Ray Traylor was also one of the most beloved performers on the roster, and by all accounts a truly sweet guy, and a devoted family man. Despite that, there was no heel in wrestling meaner or more sadistic in the late nineties than the Big Bossman.

Returning to the WWF in late 1998 after a five year stint in WCW, Ray Traylor’s nightstick-wielding alter ego wore SWAT-team black and was a committed villain, aligning himself with The Corporation as Vince McMahon’s enforcer.

Now, some would say that the most heelish thing Bossman ever did was while feuding with Al Snow. Weird Al’s pet chihuahua Pepper had become part of the company’s storylines, replacing ‘Head’ (the decapitated mannequin head he used as a prop/weapon/valet) as the object of his affections. Since the Attitude Era had no sense of proportion, poor Pepper became a bargaining chip between the two of them, culminating in the Bossman kidnapping the dog and then feeding Snow a meal that… well.

The payoff to that bizarre, cartoonish angle was the infamous Kennel From Hell, which made my list of the most unwatchable matches of all time. However, it’s my opinion that the angle that followed with the Big Show trumps that story for sheer villainy.

The Big Show’s father had just died (in the storyline - his father had passed away years before in real life), and the Bossman would continually needle him, sexually harassing his mother and reading offensive poetry ‘in tribute’ to the deceased in the ring on Smackdown. But it was the funeral itself where the Bossman upped the ante.

Dressed eerily like a comically oversized character from that year’s smash hit The Matrix, the Big Show was delivering the eulogy when the villain gatecrashed the funeral in his giant Bluesmobile cop car, this time with a hilariously huge megaphone strapped to the roof, through which he shouted barely comprehensible insults at Show and his family.

When Show lunged at the car, Bossman was able to partially run him down, which gave him time to strap chains to the coffin (muttering something brilliantly bizarre about Show’s father always wanting to be a drag queen) and drag it off behind his cruiser, with Show valiantly leaping aboard the coffin to try and stop it being carried away.