Jon Stewart is a heel. It’s official. As much as we liked him on The Daily Show, we have to hate him now. Because he’s a heel and we have to hate heels.
Usually, when celebrities show up in wrestling, they want to be cheered and promote their movies or albums or chapstick or something. But some actually like to mix it up so much that they get involved with storylines and even turn heel. So, it’s not only Jon Stewart we have to hate. Here are six more celebrities who turned heel in wrestling.
Morton Downey, Jr.
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Downey, Jr. was a singer, songwriter and shock TV guy, according to Wikipedia. And, at one time, he was a big enough star to wind up on Piper’s Pit at WrestleMania V. When the segment starts, Brother Love comes out, and Downey calls him all sorts of fat and gay to the delight of fans. He’s got the crowd on his side, then, when Piper comes out, they get in each other’s faces. This, of course, leads to Downey being a total douche and Piper’s infamous fire extinguisher spot.
Mike Tyson
Mike Tyson was a heel for, like, two weeks. After a legendary brawl with Steve Austin that changed the course of the Monday Night War, Tyson joined the heel faction DX in what was supposed to be a move to stack the deck against Stone Cold Steve Austin in his match against Shawn Michaels at WrestleMania 14. Now, how much of a heel Tyson actually was depends on what you think happened in the story. Was Tyson a mole from the beginning? Did Tyson change his mind at some point and decide to join Austin? It’s a burning question I’ve never had answered.
Dennis Rodman
He never quite turned heel because he was always a heel. He showed up in WCW already affiliated with the NWO and Hulk Hogan, and was a natural bad guy. Of course, the celebrity foil was Karl Malone, also known as the sh*ttiest dad of all-time. So, I’m not quite sure we were all cheering for the right person. To Rodman’s credit, he managed to have a pretty great brawl with Macho Man that’s probably the best celebrity wrestling match of all-time. Rodman is probably the longest-running celebrity heel, too. So, it’s natural he joined Kim Jong-un in the ultimate heel turn of all-time.
Pete Rose
He showed up at WrestleMania 14 as a sports hero. Then he proceeded to cut a heel promo on the Boston crowd. It was pretty amazing to watch. He turned heel in record time. Then Kane, who was supposed to be a heel, popped up and gave Rose a tombstone piledriver. Rose would eventually come back to get beat up by Kane and he always played a heel. So, him being a heel is something you can…*takes of shades*… always bet on.
Kevin Federline
There may never have been a more natural celebrity heel than Kevin Federline. He ruined Britney Spears! Britney! So, when he showed up on RAW, he was booed harder than anyone else in the company. People hated him so much that John Cena got cheered when they squared off. Like Rodman, Federline was a natural heel, but his mic work was impeccable. The guy showed up on RAW and asked the crowd if they wanted to hear him rap. Then he said they’d have to wait until his album drops. Guys. That’s heel work. He even got a pin on Cena on RAW. I don’t know why K. Fed didn’t just go to wrestling full-time. What else does he have to do?
Floyd Mayweather
Floyd Mayweather started off as an underdog against Big Show, so, naturally, he was supposed to be the good guy. But WWE underestimated how hateable he is. After a few weeks, they revved up his heel tendencies and let himself become a natural heel. He never did anything to signal an official heel turn, but he started showing up on TV flashing his money and running with an entourage. By the time WrestleMania rolled around, he was as much a heel as Big Show. He even used knucks to win the match. Dastardly.
