“Tulsa King” Season 2: Interview with Terence Winter

Since his Emmy-winning role on HBO's “The Sopranos,” Terence Winter has been considered a great crime writer, whether as the creator of HBO's “Boardwalk Empire,” the screenwriter of “Get Rich or Die Tryin'” and “The Wolf of Wall Street,” or the head writer of his current series, the Paramount+ gangster comedy “Tulsa King.” The origin of Winter's initial interest in the subject is a little surprising, however.

“As a young boy, I saw the musical 'Oliver' and wanted to be in it,” Winter told IndieWire. “I wanted to be the Artful Dodger.” Winter's passion for criminal enterprise was fueled by films like The Sting and Warner Bros. gangster classics that he saw on local television in New York, and as a young man he experienced firsthand the lifestyle of his childhood in Brooklyn.

“As a teenager, I worked in a butcher shop owned by Paul Castellano, the head of the Gambino crime family,” Winter said, adding that he later worked in an illegal casino run by mobster Roy DeMeo in a synagogue. “So by osmosis, I understood how mobsters act and talk in real life, and I was a fan of the genre.” When the opportunity to write for “The Sopranos” came along, Winter was ready.

“It was a natural fit. I know how these people act, talk and think, so it was fun,” Winter said. “I didn't even have to do any research.” While “Tulsa King” takes full advantage of Winter's knowledge of mob life in its story about a New York gangster (Sylvester Stallone) building a new empire in Tulsa, Oklahoma, the film did require some research, unlike “The Sopranos,” as Winter was as much a fish out of water in Tulsa as his protagonist.

“I had to face Dwight [Stallone’s character],” said Winter. “I got on a plane, flew to Tulsa, and just walked around. When I moved to LA, even that felt like Mayberry to New York to me, and everything was so much calmer and quieter in Tulsa. At the same time, you quickly realize that people are really all the same. We're all just trying to get through the day. But I got a sense of what it would be like if I was a New York mob boss just thrown into the middle of this place.”

For Winter, writing Stallone's character comes naturally; other aspects of life in Tulsa, not so much. “I grew up with pigeons and stray dogs,” he says. “All of a sudden I get out there and I'm on a farm and I don't know what I'm looking at half the time. When I write scenes with horses, I have people who work on the show who I can ask, 'How would I describe that?' I don't know how to do it myself. I'm a Western fan, but I would never try to write one because I know I'd screw it up. I stay in my lane.”

That is, “Tulsa King” Is a sort of Western — and at the same time a nod to traditional crime shows and a consistently hilarious fish-out-of-water comedy. Winter says the comedy is so embedded in the premise that he never has to reach for it; it just grows organically. “First of all, he comes out of a time capsule,” Winter said. “He was in prison for 25 years. He doesn't know what an iPhone is. He doesn't know how to call an Uber. You don't have to make it unnecessarily funny, it's just there. Just seeing this guy take a driving test or stand in line at Starbucks is comedy born out of reality, out of people under pressure or people misunderstanding each other. The comedy presents itself and you don't have to write for it.”

It helps that Winter is writing for an actor with impeccable comedic timing in Stallone; in fact, perhaps the greatest pleasure of “Tulsa King” is watching the actor flex his comedic muscles in a way not seen since “Oscar” more than 30 years ago. Winter is not just writing for but with Stallone, who is intimately involved in every aspect of the production and is co-writing the script for the season two premiere with Winter and Taylor Elmore. “You're not just getting an actor, you're getting a screenwriter, a director, a producer, an editor, a music guy, everything,” Winter said. “He's done this a million times. He has an opinion on everything. His instincts are really spot-on; he knows what he wants and what his audience wants to see.”

Winter and Stallone's collaboration as co-writers is more a series of drafts they send back and forth than they sit at the keyboard together. “I write a version of something,” Winter said. “He rewrites it for me and sends it back to me. I rewrite it for him; he writes something completely new for himself and sends it to me. I rewrite it and then we come to a point that we can agree on and that's what ends up on the screen. I've never sat in the same room with anyone and written like I've seen on 'The Dick Van Dyke Show' and things like that. I have no idea how people do that without killing each other.”

Going into season two, Winter felt liberated, having already “set the table” in season one. “Now we can have a little fun with it,” he said. “There will still be days in the writers' room where you feel like it's not productive, and you think, 'Oh my God, we didn't get anything done today.' But even saying that, you get a lot more done than you think. Even if we spend three or four hours doing it and we can't think of anything, we know what to do. not to work. And then we came up with the idea that actually makes sense. But we know the characters and the framework of the world, and that means we can now explore things. What was Dwight's daughter's childhood like? What is Tyson's [Stallone’s driver played by Jay Will] relationship with his father and what do they know about each other? And that's a lot of fun.”

Season 2 of “Tulsa King” premieres on September 15 on Paramount+.