Terence Winter
“When I got my Writers Guild card, that was the happiest day in my life up until that point. I remember saying to my sister, ‘If I die tomorrow, I’ll be happy.’”
Hungry Like The Wolf
Terence Winter chronicles his tenacious climb from unknown law school grad to sitcom writer to Boardwalk Empire creator and scribe behind the new white-collar crime saga The Wolf of Wall Street.

Written by Dylan Callaghan

(December 20, 2013)

Terence Winter is really good at writing about bad men. He made his scripting bones telling the stories of Tony Soprano, Nucky Thompson and now, real-life Wall Street con and drug abuser Jordan Belfort for the Martin Scorsese-helmed new film The Wolf of Wall Street, starring Leonardo DiCaprio as Belfort.

By his own admission, Winter is good at telling the tales of morally bankrupt characters because, on some basic level, he relates to them. None more than his latest subject, Belfort, who like Winter, grew up in New York with a deep hunger for success that led him to Wall Street. Winter left Wall Street quickly, electing to attend law school and ultimately head for Hollywood to pursue screenwriting with zero experience or contacts.

Belfort’s choice to stay was a choice, “I could have easily chosen,” Winter admits. And though the self-anointed “Wolf of Wall Street” served what some consider a modest 22-month prison sentence and was ordered to pay some $200 in restitution, he is now free, successfully working as motivational speaker and author having paid only a tiny fraction of the damages he owes. So, says Winter, there is the matter conscience that separates them. But Winter’s own ambition bordered on unreasonable – a ballsy risk-taking personality that has driven him from an unknown East Coast law school grad with zero scripting experience to one of the most respected scribes in the biz.

Winter spoke with the Writers Guild of America, West Web site about how “bad guys” lavish success seems to blind people to their gluttonous criminality and brutality, and why, in the business of Hollywood, if you don’t define yourself, others will do it for you.

The Wolf of Wall Street is based on Jordan Belfort's life and memoir. To what extent is this a bit like The Sopranos or Boardwalk on The Street – like stocks and robbers?


Photo: © 2013 Paramount Pictures
Leonardo DiCaprio in The Wolf of Wall Street.

Well, it certainly felt familiar in that the lead character is somebody who lives well outside the bounds of normal society and normal propriety. Jordan had such a life of excess and debauchery… there are certainly similarities to lives led by a Tony Soprano, for example, or a Nucky Thompson, although Jordan was real. Jordan obviously didn't kill anybody but certainly lived a life that most of us only dream about, and some people have nightmares about. It's the kind of life where, voyeuristically speaking, you look at a guy like Jordan and you go, “Wow, what must it be like to be that guy?”

What central themes emerged when you were writing this script?

It was about crossing lines in the sand and slowly becoming something very different from what you started out to be. Jordan really started out as a guy who obviously was very ambitious and wanted to be successful at all costs and really started to veer, inch by inch, into becoming a person that he didn't even recognize ultimately. It's just sort of how power corrupts, how greed corrupts, how one excess after another leads to a life that you don't even recognize as the one you started out to achieve in the first place.

For me it was particularly interesting because Jordan and I had a fairly similar upbringing; we're both from New York – he in Queens and me in Brooklyn – and both ambitious young kids. Jordan was sort of the path I didn't take that I could have very easily taken. It was actually the path I tried to take. I actually worked on Wall Street in my 20s and went to law school and then I went off to Hollywood to write and Jordan kept on the track to where he was going. It's just really easy, it seems, to fall down that rabbit hole of greed. You start to rationalize your behavior. He put drugs into that mix and just incredible excess. That behavior is often rewarded in our culture. That's another thing that the movie looks at quite a bit… I don't think a lot of these guys even feel like they're doing anything wrong, and that's sort of one of the byproducts of white-collar crime – these guys are applauded.

Winning masks the stench.

Winning at all costs. Yeah, I mean if you're making money and successful, that's the bottom line. It doesn't matter how you got there. You have the cars, the houses, the girls, the boats, everything else, the jewelry, people very often don't care. A lot of people look at Scarface, and just remember the mansion and the piles of coke and the jewelry. Even with The Sopranos it was always interesting to me that people admired Tony and wanted to be Tony, and they only looked at what they viewed as the positive aspects of being Tony Soprano or Nucky; the money, again, the girls, the power, the strip clubs, all that stuff looks like real fun.

I used to remind people that all [Tony] wanted, potentially, was to put a bullet in his head. He suffers panic attacks because he's so freaked out about the life he's living. His home life is a mess, his relationship with his wife and children are a mess, they just want to turn a blind eye to that.

Have you worked before adapting a novel or a memoir to a feature script?

No, this was the first time. I had written Get Rich or Die Tryin’. My original draft, at least, was based very closely on 50 Cent’s life, but that wasn't based on a novel, that was based on conversations with him. This was the first time I actually had a book to work with.

Tell me a little bit about how your process works when you're working with material like that.

I decided very early on one of the things I was interested in doing was telling the story through voice-over. Jordan's asides, his sense of humor, his observations about things were so interesting and so different that I thought, Wow, that just really lends itself to voice-over. It was a lot of stuff that wouldn't really make sense in dialogue, but it was just, again, his comments. I spoke to Martin Scorsese about that early on, and he was interested in doing it with the voice-over in the style of Goodfellas and Casino, so that was really great. So that's one way.

Scorsese is a master of voice-over – how much did that inspire the idea? You also obviously have this great, strong voice of Jordan…

It was very freeing. I mean I knew I could always go there to augment things that were on a page… I knew I had that in my back pocket writing the script, and it was really fun and interesting way to introduce him for the first time… There's a several minute long sequence that opens the movie with Jordan talking about who he is, where he came from, what drives him, that sort of stuff. So that I knew I would do right away. But in terms of the book, that was really just a question of the rise and fall…

Classic narrative structure.

Like a lot of gangster or crime stories are. This was, of course, the white-collar variety, but it was really just the rise of Jordan, how he invented himself and how he invented what he did, and of course, how he ended up in prison. Whether or not it actually is a real fall at the end is open to debate, given the punishment or the lack thereof for a lot of these guys. So it was just really a question of taking the timeline and then deciding what events are were going to focus on. The book is big [so] it was a question of picking and choosing the moments that I wanted to depict and in some cases combining scenes and events, and combining people – there are a lot of people that make up this story. That's the challenge of telling a story in only a few hours as opposed to writing a novel or a book.

To what extent does the use of voice-over, when done well, make the job of creating the character and creating an empathetic link with the character and the viewer easier?

Oh, absolutely. I mean you have the opportunity to hear someone's thoughts and have them explain what they're doing. I don't like voice-over when it’s a replacement for deftly done exposition, or a voice-over that's not giving you more information than is already there. If somebody's walking down the street and the voice says, “I was walking down the street…” Yeah, I see that, you know, you need to tell me something I don't see here. So in that sense when it's employed in a way that's clever or a counterpoint to what I'm watching, that's great. If you need it to patch holes in a story or dialogue then you're in trouble. If I ever had to resort to that I'd feel horrible that I'm not doing my job as a writer. But in terms of creating empathy, as you say, some of [the voice-over] is me speaking as I imagine Jordan would put something, but much of it is him, and it gives you a clearer picture of who this guy is.

How involved was [Scorsese] with the scripting stage?

Not too much. We had an initial conversation about how I'd approach it. I wanted to make sure that he was okay if I did use voice-over. I didn't want to go off on a road he wasn't interested in going down. Then I went off and I did all my research, met with Jordan a bunch of times, his parents, his ex-wife and employees, the FBI agents who arrested him and just soaked it all in. I took some field trips to Long Island where he had his offices and his house, and I sort of absorbed it all, and then I just went off and wrote.

I outlined for about two weeks, a week and a half, and then it was a very frenzied month of writing. It was like 15-hour, 16-hour days I basically locked myself in my office and just came out to eat and went back in. I just really sort of lived in that world for about 30 days straight.

Jeez, so you were doing 16-hour days?

Yeah, I can get in the zone, you know? When I'm in that zone I really don't like to break it. I like to just live in the world of the script. When I hear people take months and months on a project, it feels like so much starting and stopping for me. I'd so much rather just live in that world for as long as it takes to get it done because it just feels immediate to me. A lot of it is a function of television, too. So much of what we have to do has to be done so quickly so I am used to just saying, “Okay, we start shooting this thing a week from Monday, we need a script.” I am used to having to power through things. So the idea of writing for an entire day is not unusual.

I totally get the idea of an intensive process being better, but I am sort of marveling at the 16-hour day stretch. It seems like you would run into some stamina issues.

Yeah, I don't know. I mean, I'll get up, I'll take a nap, I'll walk around, I'll exercise, I'll stretch every hour or so just to keep it going, and coffee plays a big role. If I sense it's diminishing returns, I'll stop, I'll go to sleep, because it's pointless to sit. If I can't focus, if I find myself re-reading the same thing I wrote five times in a row or something, okay, time to take a break. I'll do other things. I'll read things that aren't part of the project I'm working on… But again, the idea of doing it in an intense, collapsed timeframe just helps me keep the entire piece in my head at the same time. I'm just much more aware of, okay, this scene is setting up something later. It's just easier just battling through it.

Is there a difference for you between the TV writing and features?

The actual writing is the same. You know, episodic TV is different, obviously, in the sense that you're not necessarily wrapping up every story. Actually, when it's working well it does feel like a movie. The best episodes I've been involved with in television have always felt like mini-movies – sort of self-contained stories that sort of stand out from the rest of the series. But the actual writing is essentially the same. I don't approach it any differently, I outline – I'm a very big believer in outlining and knowing where I'm going before I plunge in.

Succumbing to the desire to write before you have an outline is the siren song that has left so many writers dashed on the rocks and wishing they didn't dive in, you know? For me the hardest part is outlining, figuring out that story, where you're going. It's just really hard, that's the real work. Once that's done the writing of it is so much more enjoyable when you know where you're going. I totally get the impulse to say, “Oh, I'll figure it out.” Certainly great screenplays and teleplays have been written with people forging ahead. For me I've been burned more often than not by not having a pretty clear path going into it without a basic outline.

You get lost in the woods.

Oh yeah, you'll be on page 70 and realize you have no idea how this thing ends or where you're headed. Early on in my career I fell for that several times, but then I just said, “You've got to outline, you've got to figure it out.” And it's hard.

The majority of writers I talk to outline, but there's a lot of very successful ones that don't outline. They insist not outlining takes them places they would not otherwise go and makes the work fresher. How much spontaneity is still left [when you outline]?

There's a lot of room for discovery even working within an outline. I always make the analogy of driving across country from New York to Los Angeles, for example, and you'll stop in these cities along the way, that's what the outline is. It doesn't mean you can't take a day trip along the way somewhere else, go down a path that looks interesting. As long as you know basically you're heading to Los Angeles, you'll get there. So within that trip, there's a lot of room for discovery of all kinds of oddball things and characters and moments.

Also, for me it helps make connections and setups and payoffs become easier because I know where I'm heading… I'll very often stumble on something that I realize, Wow, this actually connects really well to the ending I'm heading to and it's a really great moment. I just feel the outline is sort of the person in the boat sailing alongside you as you're trying to swim the English Channel, you know? You have that if you get into trouble, you know where the story is going, and if not, you just keep paddling.

When you came out here you were a relatively freshly minted East Coast lawyer with no contacts or very few... You started in the trenches, where you kind of learned the craft on shows like The Cosby Mysteries, Flipper, Diagnosis Murder, and Xena, Warrior Princess. You've done all these incredibly prestigious shows since then, but how much of that early work do you still carry with you in your technique?

Well, to answer your first question when I came out here, it was incredibly invigorating. I felt like I parachuted out of a plane and just landed in a strange place, and there’s something really great to be said for taking yourself out of your comfort zone. I didn't know a soul in Los Angeles, I didn't know anything, I'd never been here before. I was approaching this as a complete novice. I'd never written a script before. I just knew I wanted to do it and I knew I was going to do it…

Every morning I'd wake up and realize, Oh my god, I'm in Los Angeles, what am I doing here? Oh yeah, I'm here to be a writer. It was just like a shot of adrenaline, and I just really focused on that. I lived like a monk for three years, writing stacks, just got a job where I could pay my bills during the day, came home at night and wrote.

I literally would stop at nothing, and I wouldn't go to bed at night until I asked myself the question, What did you do today to further your writing career? Unless I could answer, I wrote a scene, I sent out a script, I made a phone call to an agent, I'd get my ass out of bed and do something so I could go to bed at night knowing I am one inch closer to becoming a writer. I created sort of a phony agency to get my specs out there, to get people to read them, I applied to every fellowship program I could and eventually I got into the Warner Bros. Sitcom Writers’ Workshop. They got me placed on one of their shows, it was something called The Great Defender.

The guys who ran that show and created it were Frank Renzulli, who went on to be one of the first writers on The Sopranos years later, and George Schenck and Frank Cardea who had created Crazy Like a Fox and subsequently took over The Cosby Mysteries. I didn't know because of my naiveté, I was so thrilled to be employed as a writer I didn't look at the job offers in any kind of hierarchy. I couldn't believe people were offering me jobs to write on TV, it was a dream come true. When I got my Writers Guild card, that was the happiest day in my life up until that point. I remember saying to my sister, “If I die tomorrow, I’ll be happy. I'm so thrilled I achieved this goal.” So for me the standard of taking a job was you had to ask me, “Do you want this job?” And I would say, “Yes.” I didn't care if it was Xena, Sister, Sister, The Cosby Mysteries or anything else, I just said yes. I didn't know that people would judge me based on my credits. I thought, Well, I'm a writer, writers write all kinds of different things. Years later, of course, I realized that’s not true. You get pigeonholed, and they look at your credits and go, “Oh well, this guy's an eight o'clock sitcom writer, and he couldn't possibly write such and such…”

But you escaped, you jumped ship. You got to The Sopranos. How did you make that transition so well?

At some point I made a concerted effort to force people to look at me in a different way. I realized I was getting pigeonholed as an eight o'clock sitcom guy, for example, or soft drama writer, and I thought, Okay, I've got to write something completely different and edgy. I wrote a script that ultimately became a movie called Brooklyn Rules, which had a mob component to it. It was vastly different and got me a lot of notice in the feature world – that was my first entrée to David Chase on The Sopranos.

Even The Wolf of Wall Street is sort of a departure for me. Because of The Sopranos – and this isn't a complaint at all – I've gotten sent mostly a lot of mob/crime things so this was interesting, it was a shift away from that. It was crime of the white-collar variety but it wasn't a mob story…

But you know, the answer is, you've got to force people to look at you differently, and you do that by writing something that defies their expectations. It's just human nature for somebody to say, “Oh you want a musical guy, get the guy who wrote Chicago.” Until that person makes you look at them differently and writes a horror movie, you're going to be the guy who's known for musicals. If you're interested in having a diverse resume then you've got to take the bull by the horns.

Read how Terence Winter got Jordan Belfort to resurrect “The Wolf” in the January 2014 issue of Written By.