Terence Winter's Newest King

Terence Winter has a way with wise guys. After five years of writing on assorted series (The Cosby Mysteries; Xena: Warrior Princess and Sister, Sister), the Brooklyn native saw his TV career take off with a ba-da-bang! when he landed as a writer and executive producer on HBO's The Sopranos. From seasons two through six, he wrote or cowrote more than twenty-five episodes, amassing four Emmy Awards and twelve nominations. He won a WGA Award and an Edgar Award for the famed "Pine Barrens" episode.

Since then, Winter and HBO have enjoyed a fruitful relationship. In 2010, he created Boardwalk Empire, for which he served as writer and executive producer, collecting two more Emmy nominations; in 2016, he was cocreator, writer and executive producer of HBO's 1970s rock 'n' roll series, Vinyl.

Winter nabbed an Oscar nomination for Best Adapted Screenplay for the Martin Scorsese–directed 2013 film The Wolf of Wall Street. His other feature credits include Get Rich or Die Tryin' and Brooklyn Rules.

The latest television venture for Winter is the crime drama Tulsa King, now streaming on Paramount+. The prolific Taylor Sheridan — who's created such series as Yellowstone, 1883 and Mayor of Kingstown — created Tulsa King but turned it over to Winter so he could focus on other projects.

Sylvester Stallone stars as Dwight "The General" Manfredi, a New York mafia capo who, after twenty-five years in prison, is exiled to Tulsa to set up a new criminal empire. Winter, the showrunner and an executive producer, sat down with emmy's Graham Flashner to discuss the new series, his career and what it takes to make a good gangster pic.

Tulsa King marks Sylvester Stallone's first foray into scripted television. How was your collaboration?
They always say, "Don't meet your heroes," but he was better than I could've anticipated. One of the great things about working with Sly is, you don't just get an actor — you get a writer, a producer and a director; you get someone who's been doing this for fifty years. And he's also very collaborative.

I don't think he's ever been better in his career; he flexes muscles on this show that you didn't know he had. He brings us to places that are so deep and so poignant and funny that I don't think we got to see in any of his films. I'm really excited for people to see him.

What themes resonate for you most in the series?
We have somebody in the twilight of his years — who's lived his life believing in something and adhering to a certain code of behavior and honor — and he sort of has the rug pulled out from under him.

There's something fascinating about someone at the end of his life who realizes he's made a lot of mistakes, things that have cost him relationships with his family — in this case, his daughter. He realizes the thing he's dedicated his life to is bullshit, and he has a very limited amount of time to rectify that and limited conflict-resolution skills. He finds himself in the middle of nowhere, having to rebuild his life at seventy-five years old.

The show was initially called "Kansas City." How did Tulsa become the locale for Dwight's rebirth?
Taylor's original script was set in Kansas City, which felt a little too cosmopolitan to me. Plus, they already have an active mob presence there, so it didn't feel isolated enough for our character. We really wanted to take this guy and put him in a place that was completely unfamiliar.

The genius of Taylor's original pilot was that he took these two tried-and-true genres, the western and the gangster movie, and combined them. I wanted it to be as western, as Middle-American as possible — and for me, nothing says that like Oklahoma. As Dwight describes Tulsa, "It might as well be Mars."

What appeals to you most in writing about crime and the mob lifestyle?
I grew up in Brooklyn — that's always a good foundation to write criminals. My neighborhood had kind of a mob presence. There's always something interesting about people who do whatever they want and make up their own rules. It's fun to live vicariously through people who are just bad, because most of us aren't.

You've had the privilege of working with Martin Scorsese on multiple projects. What have you learned from him?
His notes process and the things he comments on are very simple: "I don't understand what I'm hearing." "I don't understand the story." "You're not being clear." "I can't see what he's holding in his hands." It's all about making sure the information is conveyed very clearly and in the manner you intended. Is that joke landing? Is that dramatic moment landing? Is that visual landing? It's about telling the story — that always comes first for him.

You were on track to make partner with a major New York law firm. How did you know your destiny was to write scripts in Hollywood?
I became a lawyer for all the wrong reasons. I became a lawyer to avoid being a writer, because I didn't have the courage to be a writer. It was only when I had exhausted every possibility — taking my education as far as it could go, being in a job I absolutely hated and was not good at — that I finally, in desperation, had to do some soul-searching and asked myself, "What do you want to do when you get up in the morning?" And my deep dark secret was, initially, that I wanted to be a sitcom writer.

I showed up in L.A., and failure was not an option. I purposely never took the California Bar exam because I didn't want to have a fallback. It was exhilarating. There's something to be said for taking yourself out of your comfort zone, dropping yourself into the middle of nowhere and saying, You've got to figure this out.

Fifteen years after The Sopranos ended, episodes are being dissected with the kind of scholarly analysis applied to Beatles' songs. Are you surprised at the show's enduring legacy?
I am surprised and I'm really pleased. Sometimes I get credit for things I had no idea I meant when I wrote them [laughs].... People read into things that either were never intended or, if they were intended, it was completely subliminal. [Sopranos creator] David Chase hit on something that resonated in a way that I don't think even he could've predicted. He didn't think anyone was going to even see [the show].

What was it like to work with Mick Jagger on Vinyl?
If you didn't know he was one of the biggest rock stars in the world, you'd never know it from meeting him. He was completely down to earth, funny, collaborative — to work with him and Marty [Scorsese] on the project was a dream come true. I was a massive Stones fan — the first album I ever bought, at twelve years old, was Goats Head Soup.

Were you disappointed that Vinyl lasted only one season?
I was very disappointed. We had a lot more story to tell and a terrific cast, and I was really excited about where it was headed in terms of the music history and the character development. But sometimes, unfortunately, that's the way it goes. This is a tricky business.

What's the key to writing a good gangster show?
Depicting people in all their colors — nobody is any one thing. Bad guys are not all bad. That was the genius of Tony Soprano.

It really hit home when we had a season premiere at Radio City Music Hall. Tony's sitting at the kitchen counter, eating cereal and reading the back of the cereal box — and the audience is howling. It's such a human moment, and it's like, Oh my God, he's just like me. You depict [characters] in their little human moments of insecurity, comedy or whatever, and you create something that's really relatable. I think that's the key.

Looking ahead, are there any bucket-list projects you've been eyeing?
There really isn't one. I have a few feature projects I've been working on. My interests are pretty eclectic — they go from history to music to crime to everything in between. I try to focus on one thing at one time and don't think too far ahead. I've been really lucky to be offered some great things to work on, and also lucky enough that when I come knocking on people's doors, they're interested in hearing if I have any ideas of my own.

Executive-producing Tulsa King with Sheridan, Winter and Stallone are David C. Glasser, Ron Burkle, Bob Yari, David Hutkin, Allen Coulter and Braden Aftergood. The series is produced by MTV Entertainment Studios and 101 Studios.

This article originally appeared in emmy magazine issue #12, 2022, under the title, "Men in the Moment."