‘Tulsa King’ Showrunner Terence Winter on Embracing Sylvester Stallone’s Comedy and His Scrapped ‘Batman’ Show

With the linear airing of “Tulsa King” on the Paramount Network, right after TV’s biggest show “Yellowstone,” and the announcement that the Paramount+ show will be returning for a second season after driving record sign-ups for the streamer, the world now knows how entertaining and delightful this Sylvester Stallone-led crime comedy really is.

Stallone plays a low-level mafia goon who, after 25 years in prison, is sent to Tulsa, Oklahoma, a virtually untapped resource where he can establish a vast criminal enterprise. The show is as much inspired by “Splash” as it is “The Sopranos,” with Stallone playing an F-bomb dropping fish-out-of-water – he’s not only displaced geographically, he’s also unstuck from time, having missed the past 25 years of technology, culture and societal norms.

“Tulsa King” was created by “Yellowstone” kingpin Taylor Sheridan but is executive produced by showrunner Terence Winter (he also writes on the show), who brings texture and complexity to something that could have easily been cartoonish. Winter is a veteran of “The Sopranos” and “Boardwalk Empire” (a series he created) and is clearly having a blast with the material.

TheWrap spoke to Winter about how he came on board the project, if it was a relief to take on something slightly lighter in tone and what the heck happened with his Gotham City TV series, which he was working on with “The Batman” filmmaker Matt Reeves.

How did you initially connect with Taylor Sheridan?

Taylor reached out to me, through our mutual agents, and they told me he had written this pilot, really quickly, over the course of a couple of days. It was this really interesting idea, and as you said, because he has 1500 other projects, he couldn’t possibly do anything with this. But I think it was Taylor’s idea to say, “Well, there’s one guy I think that could really take this and run with it, it’s Terry Winter. Why don’t you see if he’s interested?” And as soon as they said Taylor Sheridan and Sylvester Stallone, I almost didn’t have to read it. I was like, “Great. Where do I sign up?” But then I did read it and I loved it and I had some ideas of my own. Had a Zoom chat with Taylor. I told him what I wanted to do. He said, “Great. Take the baby and raise it. I just have visitation rights. And go do your thing.” And that’s what we did and it was great. It was a really easy process.

What was the most appealing aspect of this project for you? When describing it to somebody it’s easy to say it’s a fish-out-of-water comedy.

Those are the most, obviously, appealing elements – to take this New York tough guy character and dropping him into cowboy country. For me, it went deeper. The idea of exploring a man, in the twilight of his years, who is now questioning all of his past behavior, realizing that the thing he gave his life to, that code, that world, may not have been the best choice, and these people may not have had his best interests in mind. And he’s got a very limited amount of time and very limited resources, in which to rectify the sins of the past and still move forward and make a living as a gangster. That was the thing. I was like, “I really can sink my teeth into this and there’s nobody better to do it than Stallone.”

Was it tough to get Sylvester Stallone to sign on, especially since he’s been burned by comedies in the past?

No. I think that was very appealing to him. I think the idea that you’ve got things in this, as you said, we haven’t really seen him do before. I think people don’t think of comedy when they say, “Sly Stallone,” but if you know him, he’s really funny. He’s self-deprecating. He’s sarcastic. He’s really witty, extremely well-read. He is all the things this character is, so he was very excited to be able to show those colors. And I’m really excited to write it for him. Because, again, I don’t remember any long Rocky or Rambo monologues, but he’s got a couple in this, though, and I go, ‘Well, I can’t wait for the world to see that. Rocky can really do this – and do it incredibly well.”

There’s a video that Paramount put out of Sylvester Stallone, when the show was wrapping, saying that it was the hardest he’s ever worked. What was it like being in the trenches with him?

Well, really long days, like any film shoot, but consecutive. We were out there for, I think, almost six months, over the course of the nine episodes. We got to Oklahoma, it was freezing and then we woke up a couple days later, it was 106 degrees, and stayed that way for five months. It’s also really windy, so the song from the show, “Oklahoma,” where they say, “The wind comes sweeping down the plain,” they’re not kidding, it really does. We can confirm that. Also everybody’s away from their family, so it was like an extended class trip.

For us, it felt like the middle of nowhere, on a rough schedule, in very, very extreme heat, so it was long and hard. And he’s number one on the call sheet, and he’s practically in every scene, so he always had work to do. And just when you think your day’s over, you’ve got to go home and read lines and rehearse and get ready for the next day. I think it took its toll. It wasn’t exactly Rambo, running in the jungle, killing people, but there are different ways to have a hard day.

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People forget what a great writer Stallone is. Was having him there valuable?

Yeah. It was tremendously valuable, in the sense that you don’t just get an actor when you get Sly Stallone. You get an actor, an Academy award nominated writer, a director, a producer, an editor. He knows every aspect of this business. And he’s got ideas and the great thing about his ideas are they are never designed to make him look better. They’re never designed like, “Oh, I want to look cool, so let me do this or do that” or “I don’t want to look silly here.” It’s all about the character, and what’s best for the show, and what’s real, and what’s working. It’s never done in a self-serving way to protect himself, which I thought was incredibly refreshing. For a huge star, you don’t know what you’re going to get, and what you get here, is a guy who just wants to make the best show.

Was part of the appeal something that was a little bit more fun? I know you went through hell on “Vinyl” and, obviously, “The Sopranos” and “Boardwalk Empire” were very heavy shows.

Yeah absolutely. Its certainly got its share of darker, poignant moments, but it’s a comedy. It is a dark comedy. Really, a fish-out-of-water comedy, about a guy dropped into the middle of a place that might as well be another planet. And then that’s just inherently fun to write and the characters he’s surrounded with are absurd in their own ways, and you just sort of let these people interact, and behave with each other, and I won’t say it writes itself, but it’s certainly a lot easier than to craft a really serious drama.

What happened to the Gotham show you were working on with Matt Reeves?

Yeah. It was purely a case of creative differences. We were going to do a gritty cop show that happened to be set in the world of the Gotham City Police Department. I did a couple of outlines and just never really got it there, I guess, for Matt Reeves and company. We just decided to part ways rather than keep banging our heads against the wall, if we were seeing the show in a different way. But it was completely amicable and I know Joe Barton took a swing, as well. I think he ended up in the same place, and now they’re doing a show about the Penguin. I think it’s great.

Is that appealing to you taking on IP in that way, or have you discovered in the process, that developing your own stuff is just much better?

Yeah. It really depends on the IP. What was interesting to me was taking a serious look at a heightened animated or cartoony, I hesitate to call it cartoony, but fantasy world. Like putting the template of a gritty seventies cop show on top of Gotham City, this incredibly corrupt police department, that was really interesting to me. I’m not particularly a fan of the comic book genre, but when they presented that, and I said, “Oh, this is what I want to do,” I got on board. But yeah, it really depends on the IP.

What can you tease about the rest of the season?

I would say season one is Dwight’s long, slow planting of the flag, in a new place, and is turning his back, slightly, on his old life.

“Tulsa King” streams every Sunday on Paramount+.

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