The 10 Best Heel Turns of All Time

Green Room is the best and most underrated thriller of the 21st century. The film it reminds me the most of is The Thing. The Thing with punk rock and Nazis. The plot is simple - a band gets trapped in a remote venue after witnessing a murder and realizing it’s a Neo Nazi club. The film is claustrophobic and the pace is unrelenting. One of the reasons it’s so good is that a third of the way into the film, the leader of the Nazis shows up and it’s our beloved Jean-Luc Picard! The moral and just Professor X. Sir Patrick Stewart is the kind of actor you want as your grandpa. Green Room turns his velvety voice to one of complete menace. He speaks to our protagonists through a locked door with the same calming tone Professor X might speak to Rogue only this time he instills ti with a deep sense of dread. If you haven’t seen Green Room and are prepared for a white knuckle experience I couldn’t recommend it more. 

Julia. America’s Sweetheart. She’s never played a character more quietly disturbing than in the so called “romantic comedy” My Best Friend’s Wedding. The plot is the stuff of your average rom-com. Julia’s character is best friends with Dermot Mulroney’s who’s about to marry Cameron Diaz’s. Then she realizes that she actually loves Mulroney and now needs to stop the wedding. In a normal rom-com Diaz would play an absolute pill and we, the audience, would be rooting for Julia to get the guy. My Best Friend’s Wedding is NOT a normal rom-com. Julia Roberts plays an absolute sociopath who is determined to ruin the lives of everyone around her. Even her sunglasses scream - Professional Killer. It’s a truly evil performance. 10/10. 

A mere 2 years after uttering the famous “That’ll do pig” James Cromwell was laying waste to all of the Los Angeles underworld in L.A. Confidential. It’s a bit of a spoiler to out Cromwell as the villain, which is revealed in the final 3rd of the movie, but it’s almost 30 years old so get over it I guess. The fact that it’s a late reveal actually makes the heel turn even more impactful. During the first half of the movie Cromwell maintains much of his trademark avuncular warmth as police captain Dudley Smith, advising his police underlings and calling them boyo in a terrible Irish accent. It makes the reveal that he’s the man behind all the murder and blackmail that much more horrifying.      

The Siege is a deeply fascinating movie. The fact that it came out in 1998, 3 years before 9/11 and the War on Terror only makes it more interesting. Denzel Washington stars as an FBI agent dealing with Terrorism in New York City and plays foil to none other than John McLane himself, Bruce figgin WIllis. Willis plays a fascist army general who uses a terrorist attack in New York to place all of Manhattan under martial law and place Arab Americans into concentration camps. Willis turns down his sarcastic New Jersey charm and amps up his cold steeliness. He’s basically Sean Penn in One Battle After Another without any of the funny stuff. A future article is coming about Bruce Willis as an actor above action star, and we’ll talk more about him and this movie. The film is problematic and confusing and prescient in myriad ways and Willis is excellent in it.

Gregory Peck, with his 6’3” frame and baritone voice, was one of the best of his era at projecting the American good. He was Atticus Finch for god’s sake. But put a mustache on him and god damn could he twirl it. In life he was the Yin to Ronald Regan’s Yang. A lifelong democrat he opposed the Vietnam war, the Hollywood Blacklist, and also unlike Regan, was a good actor. Peck was even placed on Nixon’s enemies list so you know he was a decent fellow. It makes it that much more shocking that in 1978 he played the Nazi angel of death, Joseph Mengele, in a bonkers sci-fi thriller about Nazis hiding in South America trying to clone Hitler. Peck and Laurence Olivier hold the film together and prevent it from becoming an over the top farce. Could there be a more divergent pair of roles than Atticus Finch and Joseph Mengele?      

Williams had played it straight a few times before Insomnia, but in movies like Awakenings and Good Will Hunting, it was his goodness that showed through, his doctor working himself ragged for his patients. Both Dr. Malcolm Sayer and Dr. Sean Maguire dedicate themselves to the people they’re taking care of and in both films you leave wanting him to take care of you. In Insomnia Williams leaves just enough his inherent kindness in his performance as killer Walter Finch to help you understand how his victims may have been lured to him. Finch speaks with the confidence of a man who truly believes the garbage that he says, and because it’s Williams you listen, even if you don’t believe. 

Another Comedian playing a villain, this time it’s Albert Brooks. . The nebbish beloved comedic presence from Modern Romance and Broadcast News plays a gangster who wields a straight razor. Like Cromwell’s, Stewart’s and Williams’ performances on this list he doesn’t completely devoid himself of the kindliness we know of him from other roles, he simply wears it as a mask that covers up something darker underneath. The scenes where he’s playing nice then contain an anxiety because we know the mask could slip at any moment, and our familiar friend will disappear and something uglier will emerge. Many of these performance work because on some level they feel like a betrayal. What happened to the presence we know and love?!

The Paperboy is another movie I find fascinating. Lee Daniels was fresh off a double Oscar Nominee for Precious. Matthew McConaughey was in middle of The McConaissance. Cusack, Nicole Kidman, and an eager to prove himself a serious actor Zac Efron were along for the ride as they adapted a well regarded book. And this is what they made? I have already written a little about camp and this is another film I think deeply about in that regard. Did the actors think or know this was camp when they made it? Camp is something you usually can’t do on purpose so did they think they were doing something serious and prestigious? I don’t know, do you? The fact is that they made something completely unhinged, and John Cusack is at the center of it. Those who know me, know I have a deep odd fascination with John Cusack. The epitome of the 90s male. A whip smart wisecracker who can wield a gun, but is sensitive. His sarcastic veneer will fall and you will see the gooey center underneath. I’d love to have been a fly on the wall to listen to Daniels decide on who he wanted to play a dim reclusive swamp dweller. I know Loyd Dobbler! it’s a wild choice on just about every level, but somehow Cusack nails it. That is to say, nails it within the context of this absolutely insane movie.  

The courage it takes for not just an A-lister, but THE A-list superstar to play a character as detestable a Calvin Candie should be applauded. I wrote about this performance at length here, so I won’t belabor too much, but it’s still crazy to me that Titanic and Tiger Beat’s golden boy played this villainous a role.

This is it. The GOAT. The best stunt heel turn casting of all time. Henry Fonda was Tom Joad. Henry Fonda was Abraham Lincoln. Henry Fonda was Juror #8. One of the great apocryphal Hollywood stories involves director Sergio Leone pitching Fonda on playing the villain in this film. As the story goes, Leone said to Fonda, "Picture this: the camera shows a gunman from the waist down pulling his gun and shooting a running child. The camera pans up to the gunman's face and...it's Henry Fonda." The fact that it was Henry Fonda in the opening scene killing a young boy was part of what made the movie. Fonda was the Tom Hanks of his era, the moral center of countless movies. Both Leone and Fonda knew the baggage he brought to the movie and they knew the effect it would have on the audience. This is a zenith of cast against type. Not only is Fonda’s Frank murderous and greedy, but he also beds the leading lady. Can you imagine seeing Tom Hanks in a sex scene? It’s a context I’m glad we never got. In Once Upon a Time in the West Fonda nails Wrath, Lust, Greed, Pride, & Envy. 5 out of the 7 deadly sins aint bad.

Did I miss anyone? I’ve enabled comments on the Cinema Sickos site now, so feel free to yell at me there.

Happy Watching,

Matt