One on One with Terence Winter

From writing to acting to directing, Terence Winter has literally done it all on The Sopranos. He’s written numerous classic moments, like Paulie and Christopher getting stranded and eating ketchup packets in the woods, Vito getting caught blowing a construction worker and most recently, Christopher shocking the world by throwing Little Paulie out of a window. Think of your favorite moments over the show’s history, and chances are Winter wrote it.

Outside of David Chase, Terence Winter is probably more intimately familiar with The Sopranos universe than anyone on the planet. So, with only one episode of the hit show left, we sat down with Winter to ask him about the inner workings of one of the best shows in TV history, his favorite moments both on and off camera and the fate of the Russian who got away.

Where are you originally from and where do you call home now?

I’m originally from Brooklyn, Marine Park, specifically. It’s a neighborhood in Brooklyn, sort of near Sheepshead Bay, Coney Island. I grew up there, then lived in Manhattan for quite a while and I’ve basically been bi-coastal, between Los Angeles and New York, since ’91, but recently have relocated back to Los Angeles because my girlfriend and I just had a son, born April 24th. So L.A. is home these days.

How exactly did you get into writing, and when did you decide this is what you wanted to do for a living?

I kind of always had the feeling that writing was something I wanted to do, but I don’t think I had the courage to pursue it as a career. You know, you grow up on the east coast, particularly in a blue collar neighborhood, being a writer is not the kind of thing that jumps out at you as a career path. But it was sort of my deep dark secret and I began writing short stories in high school and I had a teacher who was really encouraging, but again, it was a trade school and the idea of becoming a writer was just so hard to wrap your head around, or wrap my head around.

I graduated and ended up going to college, studying journalism, still wasn’t convinced that writing was the way to go, ended up going to law school and practiced law for a couple of years and that was so miserable that I finally just did some soul searching and said, “Alright, what do you want to do when you wake up in the morning?” And the answer, again the deep dark secret was I wanted to be a writer. This was somewhere around 1991 and I had no real ties to New York at the time and I just got on a plane and moved to L.A. and started teaching myself how to be a screenwriter.

When you finally decided to pursue writing as a career, how tough was it to break into the business and was there ever a point where you thought you may have to do something else with your life?

It’s very tough. It’s a combination of talent and perseverance, initially, probably about 50 percent each. It’s sort of a Catch-22 in Hollywood that you can’t get work without an agent and you can’t get an agent without work. So, it’s almost like there’s no real set career path to screenwriting. I just knocked on a lot of doors and made cold calls to agents. I sent out my scripts to anybody who would agree to read them.

I think as Chris Caldovino probably mentioned in his interview, at one point we created a phony agency because people wouldn’t read my scripts unless they came from an agent. So luckily, I went to law school with a guy who had been bonded as an agent but didn’t really know anything about being an agent. He was a real estate attorney who had a client who wrote a book on real estate and he used the money he got from handling that deal to become an agent himself, but he never really knew anything about it, so he let me create this phony agency out of a Mailbox, Etc. and I was able to submit scripts under his name and that at least got me read. About two and a half years after I got there, to L.A., I got accepted to the Warner Brothers sitcom writer’s workshop which is a program they run every year for aspiring writers. They take about 15 or 20 writers from around the country and put you through a 10-week program. That finally got me noticed and got me put on a show.

Who are some of your influences? Was there one book, TV show or movie that you saw growing up that made you say “this is what I want to do with my life”?

I’ve always enjoyed movies. I was always a movie fan, but it wasn’t until I saw Taxi Driver for the first time that I realized that movies could be art. It was the summer of 1977, I was 16 years old and I remember sitting through that movie and it was different than anything else I had seen. And I remember going back, I probably saw it 10 times, maybe more, over that summer and for the first time realized – wow, this stuff could be really special. It’s not just some stupid action movie; this is something that’s really works on several different levels. That was the first time I had actually started thinking about film as art and that maybe writing a film is something that I would like to try to do. It was many, many years later that I actually tried to do it, but that was the first thing that sort of hit me. I do have other favorite writers – I’m a big fan of Pete Hamil’s work, mainly read non-fiction. Other than that, I just continued to see movies, but didn’t have any clear cut idea how to get into the business until years later.

Would you say you are a naturally talented writer? Being inspired by Taxi Driver, were you able to make the art movies that you wanted to write starting out or did it take a while?

No, not yet, not at all. I think what I had in the beginning, as most kids, I probably logged about two billion hours in front of the television set and I kind of knew, not instinctively, but I knew through osmosis, I suppose, what a sitcom episode should look like and sound like. I was a pretty good mimic. I could tell a story and I could do it in the fashion of the way it was done on television that I had seen through the years of watching The Munsters and Gilligan’s Island and F Troop and every other sitcom that they ran in New York at that time, so I think I was a pretty good writer. I think I was a pretty good natural storyteller. I think I was pretty funny.

The thing is, you can’t really teach somebody to be funny. You can’t teach someone to be clever, or write clever dialogue. You can teach story structure, I believe, but unless you’ve got some sort of an innate sense of humor, you’re never going to get beyond where you are. I think I had good basic tools to start with and then learn from there. I’ve read every screenwriting book I could get my hands on. I read every script I could get and really became a student of film and television. Instead of just watching movies and TV shows, I’d sit with a pad and pen and really dissect them, and make notes – 15 minutes in, this happened and this is how they end this act and this is where the conclusion comes. I really started to just dissect this stuff like when you hear kids who become electronic engineers start by taking apart radios when they were kid to see how they work. I did that with TV shows.

You wrote the 50 Cent movie Get Rich or Die Tryin’. How did that project come about and what was it like writing it?

I got a call from Jimmy Iovine, who runes Interscope Records. He called my agent and said he wanted to meet with me about doing a hip hop project and I said, “He’s obviously confusing me with somebody else.” I’m not the guy. You think immediately, “Oh, we’ve got to get Terry Winter.”

He said, “No, no, he knows who you are, he’s a fan of your work and he wants to meet you.”

So, I met with him and he said, “Look, it’s essentially a gangster story and you write gangster stories. It’s just a different culture.” He said, “Once you learn the cultural differences and the slang and the clothes, that’s all window dressing. At its core, it’s a gangster movie.”

I thought, it’s really interesting, he’s right. So I agreed to do it, I met 50, absolutely loved him from the minute I met him. The guy’s fantastic, hilariously funny, really smart, incredible businessman and I’ve said this about him about a million times, but it’s true – had he been born in a different time and place, this guy would have been running a Fortune 500 company. He’s that gifted as a business person.

So for me it was great. I went on tour with him for a couple of weeks, I interviewed him, he could not have been a better collaborator – wide open, told me everything I wanted to know. I went off, I wrote the script and then Jim Sheridan came on to direct it. Sadly, for me, Jim chose to pretty much completely abandon my script and re-write the movie to the extent that – they just made these wholesale changes that I disagreed with and it was sad because I originally was very proud of the script I wrote. The script I wrote is what got the movie green lit and then ultimately what ended up happening was the movie you see today. I just don’t think it’s as good as what I started with.

That brings up an interesting question. Since you are a writer and you don’t ultimately get creative control over the project, how often does that happen to you and what is that like to know you’ve worked on something, then you go in and you see it’s completely not what you had in mind?

It does happen quite a bit in the feature film world. It had never happened to me up until that point. In television, writers have much more control. In general, writers are the ones who run the show on TV and you’re there to make sure that your work is performed as written. I always like the analogy that writing a script is sort of like the architectural plans for a house. You turn over the script – architectural plans to a builder – the director, and he either follows or does not follow those plans.

If you’re a builder and you have the opportunity to have the architect on site with you while you are building the house, you’d think that would be a tremendous advantage, particularly if you’re going to start moving walls around and moving support beams. So if you have the writer there and you say, “Listen, I want change the scene or I want to change the dialogue – what will happen to the story if I do that?” It’s the way to do it and what happens, unfortunately, many times in feature films is the writer turns in the script and then that’s it, that’s the end of the process. Actors, directors, studio executives, etc. come along and change things without really considering what the impact of that is on the story. Its not that they don’t consider it, they may not even realize – oh, this scene sets up the last scene, etc. So many times, I’ve read scripts in their early form and go to see the movies years later and go, “I can’t believe how – this was a great script and look at the mess that ultimately gets made.”

What it did do for me is it made me a director. I sort of vowed that I would not get myself in that position again and I’ve learned to direct and, in fact, this year wrote and directed an episode of The Sopranos for the first time because I thought, I have to have some sort of control over my destiny, my writing, so that was the one good thing that came out of it.

How did you end up working on The Sopranos and what was it like when you originally joined the writing team?

I had been on a show called The PJs. It was an animated show with Eddie Murphy voiced the lead character. I was on that show and around that time, this was like ’98 or early ’99, I guess, my agent at the time sent me a copy of a TV pilot that he wanted me to watch. He said, “It’s something called The Sopranos, HBO is doing it” and like everybody else, I thought, “Why is he sending me a show about operas?” So I watched this thing and I thought it was the greatest thing I had ever seen. I just flipped out. I said, “I’ve got to be on this show.” I grew up in Brooklyn, on the sort of periphery of guys like that and I just knew I could write the shit out of this thing and I called him immediately and said, “You have got to get me on this show.” My second call was to a guy named Frank Renzulli, he and two other writers I worked with created the first show I ever worked on. Frank is from Boston and he also grew up in a similar area in Boston and I said, “Have you seen this thing, The Sopranos?”

And he said, “Yeah, as a matter of fact, I’m meeting this David Chase guy on Friday.” So Frank met David. Frank was the last person David hired the first season and David had already hired his writing staff at that point, so I sort of sat out the first year as a fan and it wasn’t until the beginning of the second season that David had fired most of the first year people and was going to bring in new writers. Frank had told him about me and David read some of my work, liked it and hired me.

What is The Sopranos writer’s room like and how is each season planned out? Does David Chase have a clear idea of how he wants each season to go or does he give you and the other writers creative freedom to come up with plotlines?

It’s a little of both. First of all, by television standards, we have a very small writing staff. I’ve been on sitcoms where there have been literally 16 to 20 writers. Dramas traditionally have smaller staffs, but most of the ones I have been on have had eight or nine writers. We’ve generally had four or five, so it’s a very tight-knit group.

Basically what happens in the beginning of the season, David will come in with a very broad stroke’s arc of what the season will hold. For example, season three – Uncle Junior is diagnosed with cancer. He has surgery, he recovers. Tony meets a woman in therapy, they have an affair; the affair ends badly. These are the sort of the bullet points that David comes in with, and then as a group, it’s our job to then flesh those things out into complete episodes.

Generally, he’ll say like, “Tony will meet this woman around episode four or five, and then they’ll begin their affair somewhere around episode six or seven and then it will end around episode 12.” And he has those bullet points for each character and these are the things that will happen to this character during the season and then our job as the writing staff is to put those things together in each episode and have them logically flow during the course of one story and that takes weeks at a time for each outline, for each episode.

Do you have a favorite character to write dialogue and scenes for?

I truly do love them all. I think I have to say I love Uncle Junior because he’s so much older than the other characters. You get to put expression in his mouth that nobody else could say. You know, the old time phrases, the old time references. It’s just a different way of speaking that people of a certain generation just don’t say, so it’s always fun. He’s also just so cranky and nasty, so it’s always fun.

You have written a number of classic Sopranos episodes, including “University,” where Ralph Cifaretto kills Tracee the stripper; “The Weight” which centers around Ralph’s joke about Ginny Sack’s ass; “Unidentified Black Males,” which has the scene where Finn catches Vito –

The blowjob episode. (Laughs.)

And you did “The Second Coming,” where AJ tried to drown himself in the pool. Out of the 25 episodes of The Sopranos that you have written, do you have a favorite episode or scene?

“Pine Barrens” is, I guess I could say it’s probably my favorite, only because it was such a unique experience for us as a crew. It was sort of a road trip for the whole cast and crew, we were up in the woods in Harriman State Park for a week in 18 inches of snow, we all stayed in a hotel up there. It was sort of fun, it was sort of like a class trip.

Plus, the episode was so much fun to do. It was hugely challenging. Originally, I did not write that to take place in the snow, it was written to take place in the cold, but it was sort of like dead leaves and bare trees. As we broke for the Christmas break that year, it snowed this huge blizzard. In fact, it just stopped snowing when we got our first shot off. You can actually see it if you watch the episode, when they are marching the Russian guy into the woods, there is snow still falling. That was the last trickling of snowfall from that blizzard. So, because it was such an oddball episode for us, it was just so much fun to do and then it just turned out so well that it was really a fun shoot for us and just a really memorable experience.

We are glad you mentioned “Pine Barrens” from season three. In the episode, Paulie and Christopher get stranded in the woods while trying to kill the Russian, Valery. Valery ends up escaping in their car, never to be seen or heard from again. We have accepted the fact that this particular loose end will never be tied up on the show, but for our own peace of mind, can you please tell us what happened to Valerie the Russian? Feel free to make up whatever answer you want, we’ll believe whatever you say. We just need to hear something.

(Laughs.) First of all, I don’t know that he took the car. Nobody knows. The truth is, I don’t know what happened to him. Our characters have speculated that maybe he died and got eaten by squirrels in the woods. We didn’t see him take the car and we just don’t know. Anybody could have come along and taken that car. It was left out in the middle of nowhere. So, the truth is, I really don’t know what happened to him. If you see him, please call me.

The Sopranos actually has a number of loose ends that haven’t necessarily been tied up. As a writer and someone who studies a lot of television and film, does it frustrate you to introduce plotlines that end up being dropped, or do you enjoy the fact that The Sopranos doesn’t feel the need to tie everything up into a nice little bow at the end of each season?

I kind of enjoy it; it’s more like real life. We’re sort of trained by decades of network television that everything’s got to be wrapped up in a neat little bow at the end of an hour and you don’t have to worry about it, you don’t have to think. The bad guy gets caught and sent to jail; the two lovers reconnect and live happily ever after, etc. We’re so programmed to think that if they are trying to find the bad guy, they will absolutely find the bad guy or that no transgression will go unpunished.

Well that’s not how life is. What we aspire to do is to tell a realistic story and sometimes, in your own life, you’ll meet somebody and you’ll think, “Oh wow, this person is going to be really important in my life” and then you never see them again. That’s how it is. It’s sort of random. And we’ll introduce – it’s not necessarily a mind-fuck or by design, but certain things get brought up and then are let go. And sometimes they do come back. Sometimes they come back years later. Characters are introduced, you don’t see them again for seasons, and then they pop up again. So, as a writer, it is freeing to not have to worry about, “Oh, I owe this to the audience because they’ll be expecting it.” There is something to be said for wish fulfillment in writing, but there’s also something to be said for thwarting the expectations of your audience and it’s in many ways more satisfying as an audience member to be left a little off-kilter. Somebody said once, “Art asks questions, it doesn’t give answers.” I’m not saying what we do is art, but it’s an interesting idea. It’s an interesting way to think about it.

People might not know this about you, but you actually appeared in a couple of the earlier episodes of The Sopranos as a character named Tom Amberson. How different for you was it to be on that side of the business?

It was really a thrill. It was fun. I had not really acted before and we were auditioning that role and David hadn’t seen anybody he really like and, at one point just turned to me while we were casting and said, “Do you want to do this?”

So I said, “Yeah.”

He goes, “Alright, well you have to read, so go down and get the sides and come back in and audition.” So I did and we ran it a couple of times and he said, “Okay, you can do it.” And then, the night came for me to do it and I rehearsed my lines for hours and I was very prepared, but you sit down and there’s the whole crew around you and the lights and the camera and Lorraine Bracco sits across from you and is looking in your eyes and suddenly, you are thinking, “Holy shit, this is not as easy as it looks.”

And then, standing up – I had rehearsed all of my lines sitting down and the director, Allen Coulter, said, “When you leave, as you’re walking, you talk to Dr. Melfi and ask her whatever question you ask.”

And, I said, “Well, wait a minute. I have to walk and talk at the same time?” (Laughs.) I remember thinking, “How do they do this? It’s so complicated.” Not only do you have to walk and talk at the same time, you have to hit a certain mark on the floor, but don’t look down to look for it, you just have to sense where it is. And this is like literally two lines of dialogue and by the end of the night I was sweating. So when you see somebody like Jim Gandolfini doing a 15-minute monologue or these long complicated fight scenes or arguments, over and over again, it just gave me – not that I didn’t already have a healthy respect for what actors do – I really thought, “Wow, this is really hard. Thank God I’m a writer because I would not last 10 minutes as an actor.”

As you mentioned before, you wrote and directed the episode “Walk Like a Man” this season. What was it liking sitting in the director’s chair and did you enjoy the creative freedom of being able to see the episode completed from beginning to end?

It was great. My biggest regret is that I didn’t direct sooner. I had been thinking about it for years and one of the great luxuries is that I had been on the set for certainly every episode I wrote myself. Basically, one of the functions of my job as a producer of the show is to sit on the set with the director and make sure that what’s in the script is actually getting on film in the manner in which we intended. So, I learned a lot over the years and I got to work really closely with some really talented directors and work really closely with the actors, so by the time I was actually directing myself, it was a pretty smooth transition.

That said, it’s a really big responsibility and it’s some high stakes. But, for me it was great. I’ve been on the show for eight years. The cast and crew completely supported me and stepped up and just made my job so easy. It was great, it was a real thrill and really to just work directly one on one with the actors was great, particularly Robert Iler, who I think is enormously talented and just did some incredible stuff for me.

David Chase has said in interviews that he has always known how the show would end. Obviously, you are not at liberty to discuss the plot of the final episode, but, as a writer, do you agree with the way Chase chose to wrap up The Sopranos or would you have chosen to do it differently?

I don’t know. I will say that I thought it was great and I think it will be a very satisfying ending.

Do you have any special plans to watch the last episode?

I am flying to New York with my girlfriend, we will be landing in New York around 6 p.m. and then I’ll be watching it with my family in Brooklyn.

How accurate do you think The Sopranos portrayal of mob life in New Jersey is and what sort of response have you gotten from real life mafia guys?

We hear back from our sources that the actual mob guys really do like the show; they’re very big fans of the show. I had an FBI agent tell me once that every Monday morning, the FBI guys who were on the mob beat would come in and over coffee, discuss The Sopranos and then they would listen to their wiretaps of the mob guys and it would be the mob guys discussing the show.

From what we understand, they really do like it. We got one piece of criticism once early on. Some mob guy got back to us through an FBI agent, I think, and said, “A don doesn’t wear shorts.” Tony was wearing shorts at a barbecue. So we actually used that in the show. At one point, Carmine Lupertazzi Sr. tells Tony, “I heard you were wearing shorts, don’t wear shorts.”

Let’s talk about your new film Brooklyn Rules. In our interview with Chris Caldovino, he mentioned that you based the main characters on him, yourself and your friend Bobby Canzoneri. How much of the film is pulled from real life and how much of it is fictional?

I’d say about 65 to 70 percent is real life and then the 30 percent that veers into the hardcore mob stuff is fiction. Certainly, the core relationships are real, the friendship between the three of us is all real and some of the dialogue is verbatim dialogue of conversations we’ve had growing up – arguments, ball breaking, that sort of stuff. So all that’s real.

For anyone unfamiliar with the film, how would you describe Brooklyn Rules?

It’s a story about three friends growing up in Brooklyn in the 80s whose loyalty to each other is tested when one of them flirts with a life in the mob.

Did that actually happen in real life?

Slightly. Very slightly. But Alec Baldwin portrays a local mob boss. He’s terrific; he’s just great in the movie. Freddie Prinze plays my character, Scott Caan plays Chris’ character and then Jerry Ferrara from Entourage plays my friend Bobby’s character. And then, as you know from interviewing Chris, Chris is actually in the movie playing a different character. And at one point, his fictional character interacts with the fictional version of himself in the movie, which is kind of too much to get your head around.

At one point, me, Bobby and Chris saw a screening of the movie and were just sitting there shaking our heads because watching three actors play you in a film is pretty mindblowing.

Now that The Sopranos has wrapped up, where do you see your career going from here? Do you think you’ll end up working on another television show or would you rather change gears and focus on movies or something else completely?

I’m developing a show for HBO right now, so hopefully I’ll have my own series in a few years. I will also continue to write films as well. The great thing about television is that it actually happens. You can develop a movie for years and it never sees the light of day. If you get a show on the air, you can get an idea, write a script, film it and it’s on the air in three months and people are watching it. It’s very satisfying; you see your work actually come to fruition.

I don’t know that I would necessarily want to work in network television again, which can be fairly frustrating. It’s just sort of writing with handcuffs on. You are just so beholden to advertisers and it’s kind of really difficult writing with the idea of “don’t offend anybody” and “make sure everybody understands every single thing you say the minute you say it.” HBO is so much more freeing and such a great creative environment that I would love to continue my career there and continue to write features as well.

Who in Hollywood would you love to get the chance to work with?

Actually, that dream came true recently. I’m writing a movie for Martin Scorsese to direct and to star Leonardo DiCaprio. It’s a movie based on a book that’s coming out in September that’s called The Wolf of Wall Street. It’s the true story of a guy named Jordan Belfort, who owned a brokerage firm in New York in the ’90s. By the time he was 26, I think he was making over 100 million dollars a year. Ultimately, Jordan went to jail for some security law violations and just had an unbelievable roller coaster ride of a life. It’s just a really, really fun project for me and to be working with Martin Scorsese, the guy who directed the movie that made me get into this in the first place is incredible.

What would you be doing for a living if you never got into writing?

Oh Jesus. I can’t even imagine. I don’t think I could have lasted as a lawyer. I was so unhappy. Man, I don’t know. That is a really good question. Whatever it is, I know it wouldn’t be nine to five and it wouldn’t be stuck behind a desk. I just couldn’t do it.

We’ve got one last thing for you here. We’re going to do a word association.

Nah, I’m not going to do that. I don’t want to do that.

Okay, fair enough. You and Henry Rollins are the two people who have refused our word association, so you are in good company.

(Laughs.) We are often confused for each other.

Interviewed by Joel Murphy, June 2007. Brooklyn Rules is in theaters now.