Going West with the Cast of Tulsa King

By Jen Chaney / November 17, 2022
Clockwise from top left: Tulsa King stars Garrett Hedlund, Dana Delany, and Andrea Savage with showrunner Terence Winter. Photo: JJ Geiger
If the Taylor Sheridan-verse seems to be expanding by the day, that's because it is. The creator and executive producer of Yellowstone, the most popular yet hard-to-find show on television, is behind multiple current and forthcoming spinoffs of the modern Western epic, as well as the totally separate The Mayor of Kingstown and, now, Tulsa King, which debuted last Sunday on Paramount+ and a special screening at Vulture Festival.

Like Yellowstone, Tulsa King features an older movie-star icon (Sylvester Stallone) as its lead, is set in the Midwest, features horses and people who like to wear boots, and addresses how difficult it is for traditional white men to adjust to the world changing around them. Tulsa King is different from Yellowstone, though, because it's also a mafia story: Stallone's Dwight is an Italian capo from New York sent by his younger superiors to set up business in Oklahoma after a 25-year prison stint.

Terence Winter, known for his work on The Sopranos, Boardwalk Empire, and The Wolf of Wall Street, took the reins as showrunner and co-creator after Sheridan penned the pilot. During the post-screening Q&A, he explained to me how he shifted the series' location and crucial plot points, while cast members Andrea Savage, Garrett Hedlund, and Dana Delany chimed in with details about working with Stallone, embracing Tulsa culture, and, for Delany, overcoming her fear of horses. The quartet also joined us in the video studio at Vulture Festival to discuss their time in Oklahoma. You can watch their conversation here.

Terence, it's my understanding that Taylor Sheridan wrote a pilot for this, which you took in a slightly different direction. Can you talk about the origin of the show?
Terence Winter: I got the greatest call ever from my agent. He said, "Hey, Taylor Sheridan reached out. He has a show that Sly Stallone is attached to and they want you to be involved in it." I said "I gotta think about that — yeah, I'll do it!" Taylor had written a pilot really quickly; he had this idea about a guy, 75 years old, mafioso, who gets sent — originally it was Kansas City. I thought it was a really interesting idea, a guy at the end of his life who's gotta reinvent himself.

One of the first things I talked about with Taylor was that, if the idea is taking a guy and putting him into a place that has absolutely no Italian American mob presence, Kansas City is probably not the best place because it's got a long, storied history with the mob. I said, "What if it's even more obscure? What about Oklahoma?" Which to me, as a New Yorker, felt like the middle of another planet. "And more specifically, Tulsa." Then I said, "What if he's just getting out of jail after 25 years, so he's really thinking he's gonna get rewarded, but he's now ostracized and sent away? And what if he's got a family, an actual family, that he's estranged from?" We started layering on all these different elements, and that's where you end up from the pilot.

And you shot a lot of this in Tulsa, right?
TW: Most of it was shot in Oklahoma City, which has a better film infrastructure, more studio space, etcetera. You probably have to be from Oklahoma to realize what's not actually Tulsa, but we did spend a great deal of time in Tulsa as well.

How was it shooting in Oklahoma?
Andrea Savage: I didn't know what to expect from Oklahoma. I really liked it! It has a really fantastic art scene, fantastic restaurants. I kept saying it feels like an early Austin. It's much more progressive than a lot of the rest of the state.

TW: Andrea and I actually stumbled onto the Pigeon Museum in Oklahoma. We went as a joke and ended up spending 90 minutes there. Absolutely fascinating.

What is in the pigeon museum?
TW: Pigeons!

AS: The history of the Fanciers, the people who are very into pigeons!

Paramount+ is calling Tulsa King "an original comedy," but it feels like a dramedy to me. How do you classify it?
TW: I wrote it with a comedic bent. You can't tell this story without being funny, even if you tell it seriously, if you don't write a single joke. And there aren't really jokes, just circumstances. You're taking a guy like Sly and dropping him into the middle of Tulsa and letting him behave with a character like Garrett's character or Dana's character or Andrea's character. It really is a mix. It is a dark comedy.

Sylvester Stallone seems like one of those figures that looms very large in the culture. I would be intimidated to meet him. How did you all feel?TW: I saw Rocky as a teenager and like everybody else in the world was like, "incredible." In 2015, he's nominated for an Academy Award for Creed, and we got invited to a dinner honoring Sylvester Stallone at Patsy's Restaurant on the Upper West Side. He could not have been nicer, and I met him for 30 seconds. They always say, "don't meet your heroes." This hero, you can meet. This guy is so cool, so funny, self-deprecating. Everything you hope he would be. And he's really smart. He's very close to Dwight, aside from the hit-you-over-the-head-and-punch-you-in-the-face stuff. But check back in a year, maybe he'll knock me out.

DD: And he's very aware that he intimidates people. He goes out of his way, especially with actors, to put them at ease.

Andrea and Garrett, do you remember your first experience in a scene with him?
GH: It was fantastic. I'd actually met Sly when I was 18, before I ever stepped foot on my first film, Troy. I went to this trainer, Gunnar Peterson — Sly's been training with him for a long time. He was climbing one of those ceiling ropes with his legs, jackknifed out, just climbing with his arms, and I was like, All right! That was a big moment for me: I'd just gotten out to L.A. and now I'm in a gym with Stallone. Over the years, we ran into each other and he was always so supportive. If he was at a restaurant, he'd call me over and ask how it was shooting this film or what I'm working on next. I was like, Man, this guy doesn't have this intimidating ego. He's unbelievably sweet. I just loved him.

AS: I was very intimidated to meet him! We'd never met before our first scene. It was at the strip club, where I come up to him and proposition him and give him a little shit, and I was, I'll be honest, very nervous. The most fit human I've ever been in a room with. We sort of ran through the scene, we were like "Is this working?" And he did a little thing with his hands, like [Sly voice] "What are you talking about?" or whatever. Dead-on impression, I know. Relax.

TW: I would have sworn Sly was sitting here.

AS: And I was like [Sly voice], "Oh, is this a guy who does this with his hands?" It could've gone either way! And he really laughed. We broke the ice right away and then we really had a good time.

One of the funny moments in this episode is when Stacy realizes his age. A lot of times, older men will hook up with a younger woman and no one acknowledges it. I thought it was great that you called it out.
AS: Terry and I talked about that when I got the script. It needed to be in there, you know? I couldn't let that be one of those moments, because that drives me insane as well.

TW: Sly even talks about it. He loves the idea that he can't believe he's 75 either. He's just as shocked as she is, in some ways. He certainly doesn't look like he's 75 or act like he's 75. He has the gait of a 35-year-old.

Andrea, we find out at the end of this episode that Stacy is an ATF agent. That seems like a problem if they continue to have a relationship.
AS: A little snag! Obviously it's tricky to navigate, and I think she very quickly realizes this isn't something she can do, but intentions and follow-through aren't always the same. Dwight and Stacy are both transplants from New York and she's going through a lot of stuff; just as he's reassessing his life in his 70s and going, Who's my family? What do I really have at this moment in my life?, she's going through a divorce, she doesn't have any kids, she doesn't have any family, she doesn't have any close friends. You make some interesting choices when you're reassessing life.

Garrett, what do you think it is about Mitch and Dwight that brings them together as friends?
GH: It ends up that we have a trust. There's something guys understand from being locked up. You got a dark past, working through some shit, it's a new future. Also, right off the bat, there's a nice little understanding that we're both fighting to not let the past define us. My character is overcoming some obstacles: He has a father that's aging, he's trying to figure out the best decision for him to get the best care, and if he can give his energy to watching his father while trying to become the best version of himself and not have to work so hard. But maybe it's hard to live happily.

With Dwight walking into the joint, it seems like an opportunity, and that's mirrored for Sly as well. He's been given the Fuck You by the boys in New York, taking over this new territory: It's all yours. So he goes out there and essentially says, if I'm taking this territory, I'm gonna fucking take it. And starts from the ground up: planting his footing there, building his empire. It's his time to shine.

We have not had the pleasure of meeting your character yet, Dana. She comes into the picture in episode three. How does Margaret get involved in this story?
DD: I play Margaret Devereaux, and she is the owner of a horse ranch in Oklahoma. Sly/Dwight comes to the ranch looking for Armand, but is telling me he's a private detective and I'm like, "What?" He's wearing a fancy suit and alligator shoes and I'm like, "Yeah, you're not a detective." So there's this dance that starts happening: He keeps showing up, and I'm not quite sure why he keeps showing up, but something is off. And then we get to know more about Margaret and maybe she has some things she needs to deal with too, that maybe Sly/Dwight could help her with. I just think of him as Sly!

AS: We keep calling him Sly! It's Dwight!

TW: Very thin line between those two.

AS: Very thin line.

Dana, as a character who owns a horse ranch, how much work did you have to do with horses?
DD: When I was a kid a horse rolled on me, and I have this fear. Terry called me on the phone about the part and I said, "I just want you to know, everyone thinks I can ride — I can't ride." He said, "Okay, can you stay on for five minutes?" I said, "Yeah, I can do that." But then I really thought, "I want to get over this." Chloe Webb, who was in China Beach with me, has become a horse therapist. She uses horses to do emotional therapy and she's fantastic at it.

She works up in Malibu, so I booked a session with her. You don't get on the horse, you just talk to the horse, and she explains that horses have been around since prehistoric days: They're on the caves of Lascaux and they're survivors because they've been prey, and that's why they feel everything — because they have to survive. And I just started weeping like a baby. I felt a kinship with this horse, because women are prey too, and that's how we've had to survive and use our emotional intelligence. I thought, Oh my God, the horse is as scared as I am! And I really got over it! I ride in the show!

Terence, Dwight has been in prison for 25 years and a lot of the comedy comes from him getting out and being like, "What's Uber?" How did you make decisions about what he would be aware of?
TW: It's tricky. In prison you're isolated to a certain degree, but you're not completely unaware of things. Things you wouldn't have access to, like Uber: You're not driving anywhere in prison, so that's something you go, Yeah, I'm not really quite sure how that works. The idea that coffee costs $5 a cup, that's something you don't encounter in prison. I haven't been in prison and I can't fucking believe it! Every time I go to Starbucks I'm like, This is insane!

AS: I feel like quite a few of them are just Terry being really pissed about things.

TW: I can barely work Uber myself!

Do you hate Soul Cycle?
TW: Not particularly, but that's another thing. And I'm very familiar with virtual reality because of my son, who spends more time in virtual reality than actual reality. Or you see people running around on scooters. Again, trying to pick the things he wouldn't necessarily know. That was one of the double whammies of fun: He's not just in a strange place, he's also right out of a time capsule from 1998.

This show is not in any way related to Yellowstone or its spinoffs and prequels, but it is part of a Taylor Sheridan universe. What do you think is the connective tissue between Tulsa King and the other shows that he's done?
TW: Horses.

That too.
TW: There's certainly parallels between a guy like Sly and a guy like John Dutton. They're rugged individualists. They do what they want, they take what they want. They're outsiders in some ways. They come in and stake a claim to things. For me, growing up in Brooklyn, the closest I ever got to a horse was Belmont Race Track, so I know nothing about that world. I had to defer to Taylor about anything Western, but that actually helped in the writing of the show, because I was just as much a stranger as Dwight is. All of this stuff is new to me. Even when I started doing research for the show, I did a three-day trip to Tulsa alone just to see what it would be like. Also, I understand that I have a slight New York accent. To see how people relate to me, and would they know I wasn't from Oklahoma? They knew immediately.

In the second episode, there's a place in Tulsa called the Center of the Universe, which is this weird little circle of bricks that's this acoustical anomaly where your voices come back at you louder than the way you speak, and it's featured in that episode. That's something I stumbled upon when I got there. So yeah, I kind of had the Dwight experience.

I'm going to ask a question that is completely in my own self-interest: Garrett, I loved your work in Country Strong. I think you have a beautiful singing voice, so I'm wondering, is there some way that Mitch can be a singer, or sing in the bar sometimes?
GH: I never thought of that. I don't know. Stay tuned.

What a very vague answer, which makes me think you're maybe singing later in the season.
TW: He does break out into The Sound of Music at one point, apropos of nothing. It's really one of the best moments in the first season. That's a joke.