Terence Winter in Sheep’s Clothing: The Wolf of Wall Street Scribe Explains How to Create a Believable Bad Guy

Terence Winter is no stranger to wolves.

With writing credits on HBO series The Sopranos and Boardwalk Empire (for which he is creator and executive producer), he has brought more snarling, beastly personalities to television screens than almost any other writer. His latest screenplay for The Wolf of Wall Street, starring Leonardo DiCaprio and directed by Martin Scorsese, takes another iconic criminal as its subject—this time, though, one from real life. Based on the audacious 2007 autobiography of the same name. The Wolf of Wall Street follows the rise and fall of money-laundering stockbroker Jordan Belfort during the ’80s and ’90s. It’s an extravaganza of drugs, sex, money, and the ephemeral power that ties them together. Winter grew up in New York around the same time as Belfort, and dreamed, too, of “making a lot of money and being important”—an urge that, while not saddling him with the dubious morality of his characters, sure has proved helpful in creating them.

We sat down with Winter to discuss finding the man in his wolf.

Kerry O’Conor, MovieMaker Magazine (MM): What sparked this whole journey?

Terence Winter (TW): I was originally sent the memoir by producer Alexandra Michan. I read it in one sitting; I could not put it down. The book is hilarious. You really can’t believe you’re reading a true story. I had been optioned by Leonardo DiCaprio’s company (Appian Way Productions), and had Martin Scorsese attached to it so it did not get any better than that. We were off to the races from there.

MM: Did you do a lot of research outside of the book?

TW: I met Jordan in real life and he was incredibly forthcoming and truthful, even about the most painful aspects of his life—and there are many. I met with his ex-wives, I spoke to the FBI agent who arrested him, I had dinner with his parents. I toured all the different places he lived. I wanted to soak in as much as possible. 

I still felt that one thing was missing: Jordan wrote about these incredible speeches he would give to his sales team a couple of times a day, and I wished we had them on tape. Unfortunately, nothing like that existed. So I said to him, “If I filled up a room at CAA with young assistants, would you give one of those speeches for me?” At first he was reluctant, but he warmed up to it. I set aside a day/ There were probably 50 people in the room, and he just became the Wolf of Wall Street. He had this room mesmerized; I could not take notes fast enough. A lot of what he said that day found its way into the actual movie. That was the final piece of the research puzzle.

The research went on for six weeks or so. Then the writing of the first draft took me three to four intense weeks, where I locked myself in my office and wrote.

MM: How did it help to meet Jordan in person?

TW: One is sort of taken aback at how boyish he appears to be. Inn the book he comes across like a slick Wall Street operator, and then you meet this funny, young-looking guy. It takes you a moment to recalibrate what you know about him and they comport that with the guy standing in front of you. But it actually explained a lot to me: “This is why the guy’s able to get away with what he gets away with so often and so well.” He is really sincere to a certain extent. He didn’t set out to be the world’s greatest supervillain. He drew lines for himself in the sand that he kept stepping over and found himself up to his neck in water, not knowing how he got there. I told Marty that I wanted to write this in the style of Goodfellas, with Jordan’s voice describing things and people. This could be a companion piece to Goodfellas and Casino.

MM: So you wrote with Leo in mind.

TW: Definitely. I was able to filter my version of Jordan through Leo’s voice and envision Leo doing it. And he did it 100 times better than I could ever have imagined it. That’s the beauty of working with an incredibly talented actor. They take something you’ve written and they’ll find a way to read a line that you hadn’t even thought of, and make it so much better and more real.

MM: Was there a difference in writing a white-collar criminal like Jordan Belfort as opposed to a man of violence like Tony Soprano or Nucky Thompson?

TW: No. You have to keep in mind that any one person is a lot of different colors. I don’t think you should set out to write criminals as bad people—most of them rationalize their bad behavior. Tony Soprano, if you talked to him, would say he’s a soldier and the people he hurts have it coming. The same goes for Nucky. So write them like real people who have a worldview that doesn’t include them being criminals.

Jordan started out wanting to be a guy who was really successful and to make a lot of money. Unfortunately, when you find yourself on Wall Street, the name of the game is making money for your firm. How you get there, no one really cares. You can see how, but for the grace of God, you may have fallen victim to that kind of thinking yourself had you been in that circumstance. Many people have.

Jonah Hill and Leonardo DiCaprio in The Wolf of Wall Street

MM: Unlike much of your other writing, this is non-fiction. Did you enjoy the reality of it, or did you find that it constrained you?

TW: A little bit of both. On the one hand, a lot of the work is done for you. You know what the story is; your job is to put it into a manageable structure. The book is huge. IT’s a big, sweeping story. The movie itself is three hours—if we told everything that was in the book it would have been 18 hours. It’s also non-linear, so the challenge was trying to find a spine for this thing, and figuring out how to hang these incidents on the right structure.

Sometimes you can get constrained by the reality of the story you’re telling. That’s a challenge we face on Boardwalk Empire as well—we deal with a lot of historical characters—and I’m not going to change history in any dramatic way. Honestly, it’s a very minor problem. This story was so rich that any instance of “Gee, that didn’t fit well,” were more than made up for. 

The biggest challenge was making Jordan not necessarily likable—I knew he would be compelling and funny—but a character that you actually wanted to spend three hours with. I wanted the audience to be seduced by these guys.

MM: Are there any changes in your methodology when writing features as opposed to television? Television is more collaborative, I imagine.

TW: It is in the sense that I have a writing staff to bounce ideas off of. In this instance, I had some initial meetings with Marty and Leo to talk about the tone and the manner with which e tell the story, but then I was in my own vacuum and I didn’t meet with them until we had a first draft.

During the writing process, it’s no different. I really need to be in the zone and do it to the exclusion of everything else. I live inside the script to get a handle on the whole thing. I can’t look out the window; I can’t listen to music; I can’t take phone calls. There’s no middle ground for me. I hear of writers who drink and work. If I had a glass of wine, the last thing I would want to do is write. I’m always amazed!

MM: “Write drunk, edit sober,” they say. You practiced law before you moved to California. Were you writing then?

TW: Being a writer was my deep, dark secret. I wanted to make a lot of money and be important. The only two jobs I knew that fit that bill were doctor and lawyer. Writing didn’t enter my consciousness as a job choice until I was in my twenties. And even then, it just seemed like something other people did.

I did train myself early on to be able to write in different locations. I knew that if, God willing, I had a career, I’d have reason to write in hotel rooms, in trailers, or in a directors chair on a set.

MM: Do you have advice to aspiring writers?

TW: Dedicate yourself to this as if your aspiration was playing professional sports. The level of difficulty of having a career in this business requires you to be that much better than everybody else at it. There’re so many people who want to do this that you’ve to to really learn your craft. Keep working at it and don’t stop until you get what you want. MM

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