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Greatest Real-Life Heel Turns

30 May

“I’m such a heel. I don’t know what came over me.” -Chevy Chase, “Fletch”

beginningGood versus evil. Heroes versus villains. Face versus heel. It is a battle that has been featured everywhere including history, television and movies. And although good always triumphs over evil (at least, we are supposed to believe this), evil seems to have so much more fun.

It has been a long-standing rule in attending wrestling events live that you always “cheer the goodies and boo the baddies.” This rule and many others are what contribute to a hot crowd and a great overall show because the wrestlers feed off of a hot crowd. They jump a little higher, run a little faster, and take bumps with a little more flair. However, true wrestling fans will have no problem respecting and even cheering for a heel if they just flourish while being one. That is why, every once in a while, if a wrestler is not cutting it as a face or becoming a main part of a storyline, they undergo a heel turn. And after that heel turn, they become main eventer and better than they ever have been. Some great examples of those who have flourished after a heel turn include Edge, CM Punk and Randy Orton, just to name a recent few.

However, heel turns don’t just happen in wrestling. They happen everywhere. In sports. Pop culture. Even history. There have been so many examples of people and characters starting out good, encountering a heel turn, and then becoming ten times better than when they first started. So in order to prove this fact right, I have decided to search far and wide for the best heel turns in movies, television, sports, music and history. Each category will feature the ultimate heel turn followed by a number of honorable mentions. Now, before you read on, a fair disclaimer: There are literally THOUSANDS AND THOUSANDS of heel turns that can be put on this list. But these are the ones that I believe are the best. You have your own opinions and I have mine. And like the saying goes, “Opinions are like assholes. Everyone has one. And sometimes they are full of shit.” So if you don’t agree with me, well then, you write an article for a website and list your favorite real-life heel turns. And I’ll read it and agree or disagree. But until that day comes, you’ll just have to settle with reading mine. Enjoy.   

Movie/Television Characters

Winner: Jack Torrance (Jack Nicholson) in “The Shining”

charactersThis was probably the easiest decision I made when it came to deciding a heel turn to be the best of its certain category. Out of the countless heel turns that have happened in the decades of movies and television, Jack Nicholson’s performance in the “The Shining”…well…shines. It portrays that classic devolution of a simple man to a psychotic killer with such ease and perfection. I remember when I first saw the movie. I was expecting to be scared out of my mind. But I wasn’t. I was more impressed with the cinematography of it all. The music played with your emotions and make you think something was going to happen, but most of the times, it didn’t. There were no moments in which something scary would pop out and scare you. All of that was taken away so the main focus of the movie would be on the heel turn of Nicholson from a loving family man to wanting to kill his own family. He went from one extreme to the other seamlessly. And it was a marvel to watch. It was the #perfectheelturn. Well, except for the fact that he died from freezing to death in a cornfield maze (SPOILER ALERT). Man, I am so glad that this website keeps me entertained. Because you know what happens with someone when they do all work and no play. Don’t be a dull boy. Keep reading.

Honorable Mentions

Harvey Dent (Aaron Eckhart) in “The Dark Knight”

It is simply amazing just how much someone’s demeanor can change when half of their face and body is burned beyond recognition. Harvey Dent’s heel turn in the movie was certainly unexpected since most of the focus of the movie was on the Joker. It was a #shockingheelturn. It kind of makes us kind of wonder what “The Dark Knight Rises” will bring.


Nina Sayers (Natalie Portman) in “Black Swan”

Trying to be the best and number one can make someone do and think some crazy things. Like your split personality is out to get you but not before it has sex with you and rocks your world. I mean, who hasn’t let their split personality go down on them, right? RIGHT? That’s a #crazyheelturn. I will say this, though. When Mila Kunis popped her head up and wiped off her mouth, I may have blown a load. Maybe.


Sebastian Cane (Kevin Bacon) in “Hollow Man”

It was the ultimate question. If you were invisible, what would you do? Try to see a hot woman naked? Definitely. Screw around and scare a couple of kids? Perhaps. Murder your entire research team in cold blood? #Scientificheelturn.


Scar in “Lion King”

While Disney movies have a long history of heel turns in their movies, Scar’s heel turn from loyal brother to Mufasa to undermining him to gain the throne was probably the most elaborate one in their movie franchise. Those who pay attention to the movie could have seen it coming a mile away, but children watching it are truly flabbergasted by it. Killing your brother, making his son believe he did and force him to run away, and gaining the throne to abuse it for your own power? #Powerhungryheelturn.

Movie/Television Actors

Winner: Michael Richards

actorsIt is no surprise that most people’s favorite part of “Seinfeld” was Michael Richards’s character Kramer. He was weird. He was surprising. He was funny. And even though success outside of “Seinfeld” did not come his way, he could not do any wrong with us beloved fans. Then one night at the Laugh Factory in California, he did do wrong. His attempt at silencing a heckler which turned into a racist rant shocked us so much. It was hard to imagine that such vile words could come from a man whose character was so warm-hearted and nice. Maybe all the hair product that he used for his crazy hair finally went to his head. Maybe all the Kenny Rodgers Roasters that he ate in that one episode really made him into a white supremacist. All we do know is that because of his heel turn at that comedy club, Michael Richards has given us two quotes that will live in infamy: One about how much pretzels make him thirsty and one about how much he loves kitchen utensils being shoved up the backside of someone with darker skin than him. Doing something so reprehensible that you have to go on late night television and apologize? #Oopsheelturn.

Honorable Mentions

Jay Leno

He warmed our hearts every late night and was the perfect replacement after the legend Johnny Carson left. And when he left “The Tonight Show,” we were all sad but fine with the fact that it was time to move on for him. Then, Leno pulled the “Brett Favre” and changed his mind and wanted to come back. And he didn’t care if it meant Conan O’Brien was out of a job. He wasn’t going to have anyone go over on him, no matter how long he was out of the game. Sound like someone familiar? If you smell what I am cooking. That’s a #returnheelturn, for sure.


Mel Gibson

The man was a genius in all the “Lethal Weapon” movies. Then, it turned out he wasn’t a big fan of Jewish people. Not only that, but a number of voicemails also put him in hot water. Guys, learn a lesson from this. If you have something angry to say to your woman, say it to her face and not on a voicemail which can then LIVE ON FOREVER. My personal favorite is when he told his ex-wife that she should “rot unless you crawl back, suck my dick, and say you're sorry. IN THAT ORDER!” The older he gets, the crazier he gets? #Alzheimer’sheelturn.


Chevy Chase

What can I say that hasn’t already been said by Mullet in his article? Just give his a read. #Douchebagheelturn.


Woody Allen

Marrying the adopted stepdaughter of your long-standing girlfriend’s previous marriage? After you helped her grow up since she was 10 years old? And it makes your adopted and biological children not want to see you or affiliate with you in any way whatsoever? #Heelturnwithabackcountryaccent.


Winner: LeBron James

sportsWhen he first emerged into the National Basketball Association, LeBron James was the quintessential poster boy. He was the boy that grew up in a small town that wasn’t exactly known for basketball greatness. He wanted to bring a NBA title back to that small town and finally put Cleveland on the basketball map. It didn’t matter if he was successful. He had millions of fans in Cleveland, Ohio, the United States, and the world admiring him and proclaiming him to be the next Michael Jordan. And then, he turned heel quicker than the Cavaliers’ championship hopes (sorry Mullet). The fact that he had to go on national television and announce his decision shows just how much of a douchebag he was turning into, and it was the metaphorical middle finger to all those fans supporting him. It’s the equivalent of when the Rock joined the Corporation just so he could be WWF Champion. LeBron left Cleveland and all the fans that adored him just so he could win championships and be successful. He turned heel on all the fans just so he could be the champion that he longed to be. Now all he has to do is win one. Or five. Or six. Or seven. Yeah, that was a scumbag move, LeBron. I’m sure Mullet would agree. Turning on your hometown just so you can be a champion and live bigger and better? #Championshipheelturn.

Honorable Mentions

OJ Simpson

He was one the best collegiate and professional running backs ever. He was a Heisman trophy winner. He had charisma and natural acting ability, which is why he starred in numerous television shows and movies including “The Roots” and “The Naked Gun” trilogy. However, in 1992, all of that changed. First, there were the murders of Nicole Brown and Ron Goldman that he was charged and put on trial for. And while he was found not guilty, he didn’t stop there. After a variety of other charges and court cases, OJ Simpson was found guilty of robbery, kidnapping, coercion, and conspiracy when he led a group of men to steal his sports memorabilia from a hotel-casino in Las Vegas. And he is currently serving a 33-year sentence and won’t be eligible for parole in 5 years. He had it all, and in one fell swoop, he lost it all. It’s a heel turn that kept going while everybody was screaming at him to stop. That’s an #unfortunateheelturn.


Michael Vick

He could do it all. Pass. Run. Score. His play on the football field amazed everybody and opened the era of the rushing quarterback. However, what everybody didn’t know was that Michael Vick could also organize dog fights and bet on them. This skill cost him 23 months in federal prison. Two years away from the game of football. And while Vick has done a face turn since he has been out of prison by going back to football, still being able to play, and keeping himself out of trouble, this heel turn was one that nobody ever expected. Doing bad, paying the price, and then turning face after? That’s a #lessonlearnedheelturn.


Tiger Woods

Number of PGA Majors Tiger Woods has won: 14

Number of mistresses that Tiger Woods had (allegedly): 13

Amount of money he lost in his divorce settlement to Elin Nordegren: $750 million

Amount of people that feel sorry for him: 0

That, my friends, is an #unsympatheticheelturn


Tonya Harding

Heel turns can happen anywhere, even figure skating. Before her heel turn, Tonya Harding was a well-known figure skater. However, later on in her career, she failed to meet the mark numerous times and beat her competition, including Nancy Kerrigan. So, in order to be on top again, Tonya Harding conspired in a plot to injure Kerrigan to the point where she couldn’t compete in the 1994 U.S. Figure Skating Championships. It worked and Harding went on to win. However, in the Olympics that same year, Kerrigan placed second in figure skating while Harding placed eighth. After that, she would face legal trouble for her plot, and she would never skate professionally again. While this is a competitive heel turn, she failed overall and now her life has come to boxing and talking on “World’s Dumbest” on TruTV. This is more of a #that’swhatyougetheelturn.


Winner: Chris Brown

musicOh man. What could be said about this that CM Punk hasn’t said? The man emerged into the music scene as a young entertainer with a big voice and even bigger dance moves. Girls couldn’t help but love him. Especially Rihanna. But then he made the ultimate heel turn by beating her up and making her face swell up like it was stung by a hundred bees. And sure, violence on women is not a foreign concept in the WWE. I mean, Mae Young has been put through more tables than I can remember. But there is a difference between pretending to harm women and ACTUALLY DOING IT. And with an umbrella (ella-ella-ella, hey, hey), nonetheless. Chris Brown has not even begun the turn back to being a face. Since that unbelievable beating, Chris Brown has smashed a window at “Good Morning America”, made outrageous comments, and even won a Grammy and think that it absolves you of all the bad he did. The fact that he has girls pining over him and willing to take a beating from him just to get with him makes him more of a heel. So what is the only way everyone will actually absolve Chris Brown of what he did? Well, an actual beating from CM Punk would do. But in any event, nothing shatters your “so cute” persona like beating a woman. That’s the #lowestofthelowheelturn

Honorable Mentions

Bobby Brown

Turning heel is certainly Bobby Brown’s prerogative. After hitting it big with New Edition and pretty much his only big hit during his solo career with “My Prerogative,” Bobby Brown’s erratic behavior came into the light. His addiction to numerous drugs (marijuana, cocaine, crack, and heroin just to top it off) and alcohol led to numerous drug possession and DUI arrests. He’s also been cited numerous times for lewd content with numerous women. However, he is probably most known for taking the beautiful singing talent of Whitney Houston and introducing her to a world of drugs and abuse. Even though he denies it, it is no doubt that Whitney Houston was never the same due to her relationship with Bobby Brown. Taking a beautiful face and turning her heel in the process? #Draggingsomeonedownheelturn.

Phil Spector

He is a famous musical producer and has worked with the likes of Ike and Tina Turner, the Ramones, and the Beatles. However, he turned heel in 2003. And I mean, REALLY heel. He killed a person. KILLED a person! And now, he is serving 19 years to life in prison. Something tells me he should have just...Let it Be. Which is a song he produced. Get it? Now that, kiddies, is a heel turn to the utmost degree. Kind of like a #playingasongbackwardsheelturn.

Britney Spears

The woman was a goddess. She had a siren voice with the sexy body to match. She was the perfect female pop singer. Then, in all of a short while, she shaved her head, started attacking paparazzi, and started acting weirder than R-Truth with Little Jimmy. It was the ultimate #goingnutsheelturn. But hey, I guess realizing how much of a mistake marrying and starting a family with Kevin Federline will do that to you.

Johnny Cash

Out of all the heel turns on this list, this is the only one that I and probably everyone else loved. After striking out trying to make it big in music with Christian gospel, Cash decided to make edgier music. Then he truly became the Man in Black. While he had several hardships and bouts with drugs and narcotics, he never strayed away from who he truly is. And that truly made him the success that he was. Trying to be good but then ultimately becoming bad because that is who you truly are? A #heelturneveryonecanenjoy.


Winner: Benedict Arnold

historyWhen it comes to heel turns and betrayals, there is no historical figure that encompasses it better than Benedict Arnold. I mean, if your name is pretty much the coined term for betrayal, then you must have committed the ultimate betrayal. For all you non-history buffs out, let me explain. Benedict Arnold was a general during the American Revolutionary War who fought for the American side. However, after obtaining command of West Point, he plotted to surrender it to the British forces. Fortunately, the plan never succeeded and Arnold switched sides eventually. But the fact that the American Revolution was almost doomed and things could have been a lot different due to the actions of one man is a very powerful thing. I mean, consider that for a second. One man could have ultimately changed this country and the way we have been living for the past 230 plus years! Betraying your country? Perhaps altering history and life today? And having your name become a term for betrayal and backstabbing? That is treason. Which is the #ultimatebetrayalheelturn.  

Honorable Mentions

Richard Nixon

If old age was a sign of respect, Richard Nixon was one of the most respectable presidents there ever was. However, all that respect went out the window when it came to Watergate. I mean, if men were going to break in and steal important information about the other party, they could have at least turned off their flashlights so that Forrest Gump didn’t see them. Doing whatever you can to win, like breaking the law? #Cheatingheelturn.



He turned on Jesus which ultimately led to his hanging from the cross and death. And for what? It’s not like he was going to be the new Messiah or something. “Some men just want to watch the world burn.” Or watch men get nailed to a cross and die. #Noreasonheelturn.


John Edwards

He could have been the Vice President of America in 2004. He could have been the President of America in 2008. However, he decided to have an affair with a former campaign worker and father her child while cheating on his wife of over 30 years who had breast cancer and eventually passed away in 2010. Not only that, but he used over $1 million of political donations to hide the affair. I’m still deciding if Edwards or Vince McMahon portrayed a worse husband. In any event, that’s a #doubleheelturn.


The United States of America

The early treatment of the Indians. The South seceding and fighting the North in the Civil War. The Asian-American internment camps during World War II. Dropping the Atomic Bomb. Needless to say, there have been a number of heel turns. However, America is currently a face and has been since its face turn back in 2001. Which just shows you how much the cycle goes round and round from heel turn to face turn and back again. And how, sometimes, good heel turns can be forgotten. That is the #forgottenheelturn. Please, never forget…heel turns.


Hopefully you enjoyed the article. If not, I’m going to pull a heel turn and take it out on somebody. What kind of heel turn will I take? Well, after reading this article, there are certainly a number of them to choose from, wouldn’t you think?

Follow Whidden and all of his unbelievable heel turns on Twitter @MKWhidden. Also tweet @Podswoggle some more great real-life heel turns using the hashtag #RealLifeHeelTurns

Michael Whidden

Michael Whidden

Been Watching Since: 1994

Favorite Wrestler, currently: Kevin Owens

Favorite Wrestler of All Time: Stone Cold Steve Austin

Least Favorite Wrestler, currently: Matt Hardy

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