02/15/2012 09:31 am ET | Updated Apr 16, 2012

An Interview With Terence Winter: Executive Producer and Creator of HBO's Boardwalk Empire (Part 2 -- On Writing for TV)

In his role as showrunner for HBO's Boardwalk Empire, Terence Winter usually gets a fast response from any agent he calls. This was not the case in 1990, however, when he was 29 and trying to break into television. As a newly minted lawyer, a Brooklyn native transplanted to L.A., and an aspiring sitcom writer, he followed up with agents who'd agreed to read his scripts, but soon gave up in frustration when he realized they couldn't distinguish his carefully crafted spec episodes from the hundreds of other submissions on their desks.

A less determined person might have renounced his ambitions, but Terry Winter sized up the situation and devised a creative solution. After learning that a New York-based law school colleague was bonded as a literary agent, he made the following offer: using his friend's name on the letterhead, Winter would fund the creation of a new literary agency (which consisted of an answering machine and P.O. box) and would pass on ten percent of whatever he earned as a writer. His friend agreed, so Winter moved ahead with the plan, submitting spec scripts to the 26 network sitcoms on the air, fielding calls if producers phoned back and even serving as his own messenger.

Winter's luck suddenly changed with a Friday afternoon call from Winifred Hervey Stallworth, then showrunner for The Fresh Prince of Bel-Air. She asked to see a teenage-slanted script, so that weekend Winter whipped off a spec episode of The Wonder Years, then delivered it to the Fresh Prince office the next Tuesday. His work impressed Stallworth who invited him to come in and pitch ideas. Having cracked the door open with his ingenuity, he made some contacts that eventually led to his first writing assignment: an episode of The Great Defender. Over the next five years, he wrote for many other series including Xena: Warrior Princess, The Cosby Mysteries, Flipper, and Sister, Sister, rising to producer for the latter two. Then came The Sopranos, the epic show for which Winter won four Emmys, three Writers Guild Awards, and an invitation from HBO to create his own series, Boardwalk Empire, which will launch its third season this fall.

In Part Two of our phone interview, Winter speaks about his unexpected admission to New York University; his decision to follow his heart and become a writer; his special regard for three mentor-colleagues -- Martin Scorsese, Frank Renzulli, and David Chase; and his 2007 film, Brooklyn Rules.

The way you broke into TV should give hope to all young writers. But how did you find the nerve and the courage to pursue such an independent path when you had to do everything yourself, even donning a baseball cap to deliver your own scripts?

It's not really accurate to say 'nerve and courage' because my choices were born of unhappiness. I knew I'd made a terrible mistake by initially pursuing a legal career [he attended St. John's University School of Law], but that was the result of somehow thinking that a law degree was the validation I needed before I could pursue what, in my heart, I wanted.

The idea of growing up in Brooklyn and saying, 'I want to be in the movie business and be a writer' -- who does that? Other people do that. The idea was to be a cop or a fireman. Even a lawyer was a big stretch -- that was a huge deal; I didn't know any lawyers as a kid. So the concept of Hollywood was just so remote. It wasn't until I was in my late twenties and starting to develop more self-confidence that I thought, 'Do you want to stick with something you're really not good at it and really not enthused about just because it's safe and respectable, or do you want to have a life you can really embrace and that allows you to reach your full potential?' Once I was able to make that choice and say out loud, 'I want to be a writer,' the world really changed for me dramatically. And I finally said, 'I'm going to go for this,' so I got on a plane and went west. And I showed up in L.A. with a really intense work ethic and a real drive to succeed, and I planned to live, breathe, and eat writing until I made this happen -- and that's what I did.

It's amazing that you became a lawyer since you were not on a college-prep track in high school. Will you tell me how you got into New York University?

I was going to a vocational high school in Brooklyn, studying to be an auto mechanic. When I decided I wanted to go to college I had no background, but I wandered into Greenwich Village and stumbled across NYU and thought, 'This looks like a good place. I'll go here.' The truth? That was the extent of my college research. But after I read the application and brochure, it became clear that I probably wouldn't get in with my auto mechanic courses. Yet I thought that if I picked a major nobody else wanted, maybe I could eliminate my competition, so I chose the most obscure major they offered. Well, I got a call from a man in admissions at NYU a couple of weeks later who said, "You're from Brooklyn and you're studying auto mechanics and now you want to study medieval history?" And I said, "Well, I've always loved the Knights of the Round Table." Which was a lie. But it was the only medieval thing I could think of.

And the guy said, 'Okay, that's interesting," and a couple of weeks later I got a letter accepting me to NYU conditionally. I was a terrible math student so I needed a couple of extra math courses, and I also needed a foreign language. But there I was accepted to NYU, not having read anything for years except Popular Mechanics. [Laughs] I'm exaggerating, of course. I did read a lot as a kid. I was always interested in history. And by the way, I paid for both college and law school with student loans. You name the job and I did it. I was a cab driver, a hospital security guard, and at one point a New York Times paperboy responsible for three neighborhoods in Brooklyn -- I was 21 and had to deliver 400 Sunday Times at three in the morning. I was also the midnight to eight a.m. doorman at an apartment building on the Upper East Side.

I've read that seeing Scorsese's Taxi Driver was a turning point in your life. How so?

The minute I saw it, I knew I'd never seen anything like it before. The look of it, the darkness of its subject matter. Ultimately, I came to realize it was more European in style -- of course I didn't know that then; I didn't know what I was watching. I just knew I loved it, and it was the first film that got me thinking of movies as an art form, and I saw it well over a dozen times that summer. And I wondered, 'Who made this movie? Who is this guy Martin Scorsese?' Then I read about him and learned about films that influenced him, and I'd try to see them but it was really hard. This was 1976, pre-VCR, and unless you took the subway and went to art houses that ran revivals, you didn't get to see them. You might catch some on TV late at night, but you really had to make a great effort. Then 1984 came around and the first video stores popped up, and I didn't leave my house for three months. I just rented everything I ever wanted to see.

You must have been happy when you got to work with Scorsese on Boardwalk.

It was ridiculous. I started to question whether I was dreaming all of it. I still don't know how to describe it. It was mind-blowing. The idea that I could go to his house and pitch him on something and work with him -- well, if you'd told me that in 1976... He's now a friend and a colleague and a partner, and it's absolutely a thrill.

Can you talk about the importance of other mentors?

I joined The Sopranos in 1999, and we were writing the second season while the first season was still on the air. One of my mentors was David Chase [creator, showrunner, and head writer], and he gave me great advice. For The Sopranos particularly, he told me to stop writing like a sitcom writer. One thing I tended to do was to set up funny situations as opposed to just being honest, but he said that if you depict these people honestly, the humor will be there. And David's biggest mandate was to be entertaining. Your job at the end of the day is to entertain the audience -- so you need to ask yourself, 'Is my stuff funny or clever or interesting?'

Before David was a guy named Frank Renzulli, one of the people who gave me my first job. Frank co-created The Great Defender which ultimately led to my first job in television. He and I became good friends and over the years we kept in touch. After I saw the pilot of The Sopranos, I called my agent and said, 'You have to get me on the show. It's terrific.' My second call was to Frank Renzulli. He said he'd seen the pilot and was meeting with David Chase that same week. I said, 'If you work for that show, you have to get me on there with you.' But Frank became one of the last people David hired, and the door closed, and there wasn't an opportunity until season two. So finally David asked Frank, 'Who's this guy you've been telling me about?' and so Frank was hugely instrumental in my career by helping me make that connection.

While you were writing The Sopranos, you wrote and were executive producer of the film, Brooklyn Rules. It's the story of three boyhood friends and is largely autobiographical. How did it feel to see your life depicted on screen?

In some ways it was tremendously satisfying, but in other ways it was bizarre to see three actors portraying me and my two best friends, having almost verbatim conversations on screen that we had in Brooklyn. And I was sitting there with them watching a cut of the movie and this was one of those moments when you think, 'This isn't really happening, this is a dream.'

Despite your success, you still seem to have a sense of wonder about what you do.

I am privileged to do this for a living. I come from a place where I never thought people liked their jobs. So the idea of doing something you love, creating things and telling stories and working with other really talented people -- and they pay you pretty well! -- is incredible. But I don't think of this as luck because I really worked my ass off. At the same time, I feel I haven't had a job since 1994.

Have you ever considered writing a memoir?

Yeah, I keep a journal, and I'd like to. If my experience could give someone else insights into how the business works, I'd be happy. I think what people don't realize initially is that it's 50 percent talent and 50 percent perseverance.

What's your main advice to aspiring TV writers?

As I've said before, nobody ever rang my doorbell and asked me to show them a script. You've got to get it out there, and if you're not willing to put the work in you can be the most talented writer in the world but your script will be sitting on a shelf. And then it's a delicate balance between being assertive and being a pain in the ass. You've got to know where the boundaries are and walk a tightrope. But you've got to get it out there!

What are some of the advantages of working in cable versus network TV?

You can depict things honestly. You can show people as they really are -- the way they really talk and think. I don't know if I can say this for all cable TV, but I can certainly speak for HBO. The manner in which we tell a story is very different. I think HBO assumes the audience members are really smart. There's no dumbing down of the material, no pandering or cowardice. The notes you get from HBO are not born of fear that people won't buy the soap anymore. They're not concerned whether the advertising executives are happy. It frees you up tremendously. It's a whole different way of working.

Where do you see yourself in ten years?

I'll be 61. [Laughs] My one goal is to read a book that doesn't have to do with something I'm writing. I can't remember the last time I read a novel. But [writing and producing] is what I want to do every day. If I could continue to do this, that would be terrific.