Terence Winter
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Oscar-nommed scribe reveals an early affinity for the underbelly of life

Terence Winter is Oscar-nominated for adapting Jordan Belfort’s memoir “The Wolf of Wall Street.” Winter spent years working on sitcoms, then writing characters who are fascinating but unsympathetic on “The Sopranos” and “Boardwalk Empire.” Here, he talks about the circuitous path to his writing career.

What was your childhood like?

I grew up in Marine Park, Brooklyn, the last of five (children). My dad died when I was 7, and my mom went back to work as a secretary at Texaco. She was in her early 40s with five kids to raise, and my dad didn’t have any life insurance. So all credit to her.

What did you want to be when you were 10?

A con man. I discovered Abbie Hoffman’s “Steal This Book.” That was like a bible to me, it was all about how to steal things, how to make free phone calls, to shoplift. It introduced me into the world of criminals and con men. Around that time, I saw “Oliver!” I wanted to be the Artful Dodger. Or a baseball player.

Any early career paths?

I studied auto mechanics at William E. Grady Vocational High School. But when I was a junior, a teacher made us write short stories. She said, “You’re a talented writer; you should go to college.” I wanted to open a deli.

What was a turning point for you?

I was living in a basement apartment and I had an epiphany: If I didn’t make something of myself, I’d be in that apartment for the rest of my life. I was determined to go to college. I was walking around Greenwich Village and stumbled upon NYU. That was the extent of my college research. I thought if I pick a major no one else wants, maybe I’ll eliminate my competition: They offered a major in medieval history. So suddenly I’m in NYU. I had no money and no idea how to study, but I was determined. It was a matter of going to school full time and working full time at night. You name the job, I did it: taxi driver, security guard at an emergency room, the guy who delivered the New York Times. I was the midnight-to-8 doorman on the Upper East Side. I ended up majoring in journalism and political science.

What were your goals?

My ambition at that point was to be rich. So I went to law school at night. During the day, I worked in the legal department at Merrill Lynch. I was on the trading floor when the stock market crashed in 1987. That scene (in “Wolf”) where the bell goes off at 4 o’clock and it’s dead silence for about a minute and people were just standing there and finally saying, “What the fuck just happened?” — that was taken from my experience. A quarter-mile away, Jordan Belfort was working for L.F. Rothschild. When I (later) read his book, I thought, “I understand this guy.”

The second epiphany

I ended up practicing law for a couple of years and I was successful, but miserable. My deep dark secret came to the surface: I wanted to be a sitcom writer. I didn’t want to be rich any more. I quit my job, sold everything and went to L.A. in 1991. I lived like a monk for three years, just writing scripts. I learned it wasn’t about the pursuit of money, it was the pursuit of something I was passionate about.

How do you work with unsympathetic characters?

I’ve realized if you paint any human being in all the colors of emotion and psychology, people will find moments of empathy; even the worst person is a human being. With “Wolf,” we just wanted to present his story without judgment and let the audience make of it what they will. We just wanted to hold up a mirror to what’s going on on Wall Street, what has gone on, and what continues to go on.

Did financial colleagues like the movie?

All of them loved the movie. Most people say it’s accurate — and in some cases, doesn’t go far enough.

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