‘Tulsa King’ Boss on Working With Sylvester Stallone & What to Expect in Season 2

It’s almost time to head back to Tulsa to spend some more time with The General. On Sunday, September 15, Tulsa King Season 2 kicks off with its premiere episode “Back in the Saddle” on Paramount+, and it’ll pick up right where the first season left off. Dwight Manfredi (Sylvester Stallone) will find himself in deep trouble after being turned in for his attempted bribery by Stacy Beale (Andrea Savage), putting his newly established business and freshly reestablished family dynamics at risk.Season 2 will also see him facing some new foes as the series ushers in Neal McDonough and Frank Grillo to challenge his authority in T-Town. So what can we expect from these newcomers? And what else should we know about Tulsa King ahead of its Season 2 debut? TV Insider caught up with showrunner Terence Winter to find out.Sylvester Stallone didn’t really do TV before this. So what made him right for this? And then how did you convince him to do it?Terence Winter: Our great good fortune was that he was interested and he was open to doing TV. And I think he had some early conversations with Taylor Sheridan about the concept of what it would be. And then once I came on board and we had our pilot, he read it, and he called me up and he said, “This fits me like a tailor-made suit. This is me. If I were a gangster, this is exactly who I would be. This is exactly how I would talk, exactly how I would relate to people.” So once he got the the pilot, we had some initial conversations about who Dwight is and what his back story was and where he was going, he was on board. All of us I speak for, everybody could not have been more thrilled. Speaking of suits, Dwight is kind of a fashionista. Was that intended, or did Stallone kind of bring that to the project? I think a little of both. I mean, Sly in his real life is a pretty sharp dresser. And I think a guy who spent the last 25 years in an orange jumpsuit really wants to kind of maybe dress up a little bit. But it’s funny, too, to even see the development as he gravitates and becomes more of a midwesterner. He starts to have more of a little bit of a Western feel — those bolo ties and the belt buckles and the good boots and stuff.

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'Tulsa King' Season 2: Trailer, Premiere Date, Cast, Details

So he’s starting to integrate himself a little bit into his own environment, but he’s still clearly a New Yorker and a New York mobster. You don’t get a lot of guys wearing shiny suits out in Tulsa. 

Of all the Taylor Sheridan shows that are out there right now, I find Tulsa King to be the funniest one. How do you thread that needle between the darker dramatic moments and then honestly some laugh out loud moments?

A lot of the comedy is just really born of reality. I mean, first of all, the fish-out-of-water nature of the show just sort of lends itself to comedy. You take a guy like that, this New York mobster and drop him into the middle of what he considers to be the middle of nowhere, with people that he would not recognize in a million years — everybody’s super polite —and then put them in situations that the rest of us are stuck with… Put a mob boss in the DMV — and it’s like, it doesn’t matter who you are, that’s a horrible experience, and you’re gonna deal with it —or you have to try to wait on line at Starbucks like everybody else. Seeing the mob boss go through those things is just inherently funny.

So for me, I felt like, we don’t even have to write to the comedic if you just write to the reality of this situation and just talk about like Dwight’s take on the world and how things work and the illogic of getting through the day to day. The comedy is kind of just there. So it’s great, and the truth, really, too.

I’ve met a lot of real-life mob guys, a lot of them are really funny – until you owe them money, and then they’re not funny at all. But some of them are great storytellers and they’re really smart. And Dwight is no different. So it’s kind of a natural, I think, if you just let them be and you show those characters in all of their colors as a person, you’re gonna get moments of comedy and also moments of deep, deep drama and violence and all the other stuff that goes with it.

Paramount+

Speaking of your history with mafioso types, obviously, this is not your first rodeo, so to speak when it comes to TV shows about mafiosos. But this one feels almost like a little bit of wish fulfillment. There was a Sopranos episode when Johnny Boy wanted to move out West. I wondered if that played any part of it.

Well, I mean, I inherited the concept from Taylor, but immediately it resonated with me as soon as I said, “Wow, what a great idea. This is a wonderful set-up. I can just immediately see the possibilities here. ” So it was kind of wish fulfillment for me in that sense — except he thought of it first. 

What is Dwight’s superpower? Is it his charm or his intimidation factor?

I think it’s a little of both. I mean, I think the fact is that he is, at his core, a reasonable person, he’s not a bully. I think if you were born in a different time and place, he would have been a businessman and a pretty good one. The fact that he grew up to be AAA mafia. So it was a situational circumstance. But I think he brings with him a natural charm and reasonable nature that I think he treats people decently until he decides they don’t deserve that… For the most part. Obviously, he’s done some thuggish horrible things. But for the most part, again, he’s not a bully as some of these guys can be, and he’s basically a decent person. And I think that’s sort of what sets him apart. 

This season we have a couple of newcomers, Frank Grillo and Neal McDonough.  Can you tease a little bit about what we can expect from them, what they’ll bring to the show?

Sure. Well, both of those guys are actors I’ve been wanting to work with for years. I mean, Neal, I’ve been a fan of for forever. And in terms of casting, both of them are rivals to Dwight in different ways. Neal plays a rival businessman who’s equally an alpha male, and we did need actors who could stand toe-to-toe with Mr. Stallone and not get eaten up. Sometimes you see on screen actors that they’re getting eaten alive. We needed somebody that’s got those eyes like Neal McDonough who can look Sylvester Stallone in the eye and you go, “Yeah, this guy is not afraid.” And Sly knows he’s up against something real. Same thing with Frank Grillo, who plays a rival mob boss in an adjacent city who’s not happy to hear that there’s somebody in what he considers his turf. 

So you know, they bring a lot of conflict to the show, which, of course, is always the essence of drama and comedy. They’re both two great additions to the show, and it’s fun to see how it plays out. 

Paramount+

For Neal McDonough specifically, he’s been in another Taylor Sheridan show, Yellowstone. I’m wondering, is there any chance of a crossover with this show and some of the other series?

You know, we haven’t discussed it, but it’s certainly [possible]. They exist in the same universe, so anything’s possible. I mean, that’s a good question. I’m gonna call Taylor Sheridan later and ask. 

Just in general, what’s your creative process with Taylor and creating a show with him?

I inherited the original pilot that Taylor wrote. He wrote the pilot actually in the course of like three days from what I understand and he basically just turned it over to me and said, “I’m too busy to do this. This is your baby. Just take it and run with it.” And that’s what happened, and I did so. Really, that’s the extent of my involvement with Taylor. I’ve only met him once actually in person and then he’s gotten gone off to do his 100 other shows and I just took this over. 

Once he gave me the template for the show, we took it and then developed it. And I understand he’s a fan and likes it, which is great. So that’s basically it.

The first season, if we were to characterize the theme about establishment, reclaiming a sense of self. How would you describe the theme of Season 2?

As you said, Season 1 really set the table with the guy who’s, rebuilding and, and forced to rebuild and a man who’s in his later years who’s only got in his mind maybe 10 good years left to make something of his life and to repair the mistakes of the past. Season 2 is about building on that. Now he’s surrounding himself with a core group of people that he loves and respects, and now he’s going to try to make that dream come true of legitimacy and stability and home and all the things that he wasn’t able to do, certainly in his whole life, and specifically the last 25 years. 

Of course, a guy with limited conflict resolution skills and limited abilities to stay legitimate, there’s challenges, and there are other people, of course, who are pushing back on that.

So it’s easier said than done. But he’s trying to build. He’s trying to build a life that he can be proud of. 

Tulsa King, Season 2 premiere, September 15, Paramount+