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How To Write Flawed Heroes, From The Writer Who Perfected The Art Form

Terence Winter, writer of Oscar-nominated The Wolf of Wall Street and The Sopranos and creator of Boardwalk Empire offers some insights into writing complicated heroes.

Lots of screenwriters strive to make audiences fall in love with a character or view them as evil incarnate; fewer can go on to make those viewers feel conflicted about their choice. Long before Breaking Bad gave viewers constant gut-checks about whether they still wanted Walter White to succeed, The Sopranos provided similar uncertainty. Tony Soprano was not the first troubled hero to murder his way into our hearts, but as critic Alan Sepinwall points out, he just may be the modern prototype. As it turns out, the guy who wrote more episodes of The Sopranos than anyone else went on to bring even more wildly flawed lead characters to blistering life afterward.

Terence WinterImage: Stephen Lovekin | Getty Images

That writer, Terence Winter, is the man responsible for Boardwalk Empire, a show whose main characters are corrupt politicians, bootleggers, and gangsters. He also recently wrote the screenplay for Wolf of Wall Street, which was directed by Boardwalk co-conspirator Martin Scorsese. That film, which was nominated for several Academy Awards, followed the exploits of a smooth-talking sociopath, whose magnetism made the film watchable though what we were seeing was repugnant on many levels. Winter spoke to us recently about how he's taken a wide roster of charming killers from concept to, uh, execution.

Mine Your Environment (It Helps If That Environment Was A Mob-Affiliated Meat Store)

I grew up in Brooklyn and worked in a butcher shop that was sort of run by mobsters. Well, not run by mobsters, but ultimately owned by a very big one. It’s just sort of osmosis when you grow up in a neighborhood like that; you rub elbows with people who are in that world, and I obviously never had anything to do with it, but I kept my ears open and my mouth shut, and I was sort of able to figure out how these guys thought, and what the psychological process was—the basic tone of their demeanor.

Just Listen

I love eavesdropping on people and listening to people talk. Just the different rhythms they have and turns of phrase, the things weird people put in a colorful way. Things that just sort of ring funny on your ear. New York is such a crowded place and you can’t help but interact with people all the time. Put a bunch of lab rats in a crowded space, they’re going to start fighting and pecking at each other. And it was definitely like that here in the ‘70s, you were just sort of thrown into this psychological experiment of "Let’s cram too many people into one space, turn the heat up, and see what happens." What happens very often is people argue and get into fights and break each other’s balls. I didn’t know it at the time, but it was really an education in how people under pressure react to each other.

You Can Show Any Point In a Character’s Life, So Choose Wisely

There’s a lot less real estate to tell a story in a feature. Fortunately, we were very lucky to have time on The Sopranos and Boardwalk to have hours and hours to get inside a character’s head and make a case for them one way or another. It’s a great luxury. It’s like writing an epic novel—you get to know more about these people than you ever would in a feature.

For instance, every movie you’ve ever seen about Al Capone shows him at the height of his power, and sort of like Al Capone’s Greatest Hits. If you can only spend two hours with Al Capone, you want it to be when he’s at the top of his game. On Boardwalk, we meet Al Capone when he’s a kid driving a truck. That Al Capone is so much more interesting to me because we get to see him become the guy we know, and we had hours and hours to do it, and really see what formed him and what made this guy tick and that’s so much more a luxury as a storyteller and more satisfying for the audience.

Different Actors Project Different Kinds of Menace; Write Accordingly

Someone like Jim Gandolfini, who is absolutely physically tremendous and imposing, he can do a lot with a little. On the flipside, an actor like David Proval who played Richie on The Sopranos in season 2 was unbelievably scary, and he wasn’t a big guy. He has more menace in his eyes than most actors do in their entire bodies. He didn’t have to yell or ever raise his voice. He’d just look you in the eyes and say the lines and you’d totally believe it. You were ready to hand over your wallet or anything else he wanted in a heartbeat. It wasn’t about physicality, it was about attitude and demeanor. It really depends on the actor.

Your Antihero Need Not Be Likable—Just Real and Entertaining

The rule for me is that the character has to be compelling and interesting and entertaining. Are you entertained?

Likable is not high up on my list. It doesn’t hurt, of course. Relatable certainly helps too. I think in any character or any bad person, if you show those people in all their colors, you’re going to find moments of humanity, even if it’s the worst person in the world. Al Capone is a great example on Boardwalk Empire. Here’s a guy who’s a horrific figure in history and killed dozens if not hundreds of people. But if you get to spend time with him as a character and see him at home, and his relationship with his deaf son, you start to feel for the guy. He is a human being at his core. We all are. Even the worst of us, if you see all aspects of that person, you’re gonna find moments of, if not empathy then relatability and maybe you’ll have moments where you go, "hmm, at times, even Al Capone could have a soft side." Maybe you won’t.

Your Antihero Can Indeed Go Too Far, But Maybe Shouldn’t

If the story takes a character [beyond redemption], that’s where it takes it. If it gets to the point where people don’t want to watch anymore, then that becomes a problem. I think there are certainly characters that skirt that edge. I think anybody who hurts animals—that’s one of the traditional things that’s unredeemable. Anyone who hurts children—completely unredeemable. That’s a character that I wouldn’t want to watch. It would be too uncomfortable for me. The irony is, you can see a guy kill 50 people, but don’t hurt a dog. Obviously, a dog is entirely defenseless and innocent, and you can make the case that it’s just gangsters killing each other and it’s different. Killing animals is something that might make you not only not be on board anymore, but you might not want to watch the character at all.

[Images courtesy of HBO | Paramount Pictures]

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