"Shooting in Cuba was something we talked about in the writer's room almost immediately when we were thinking about big ideas for this season and what we were trying to accomplish," Don Cheadle tells me of the new season of Showtime's House of Lies, which became the first American scripted television production to shoot on the island. "My character was thinking about potentially selling his business, in a sort of Faustian Pact, so our goal was to make it sweet enough for him to sell his soul, which has always been up for sale. Going to Cuba played right into that."

"I got to go there and scout," creator Matthew Carnahan told me. "The actors only had the experience of the limited time we were shooting there, but I had unbelievable access to things that people don't get access to. There's really a thriving artistic community and a great film and television scene in Cuba that none of us really knew anything about before this."

Carnahan hatched the idea for House of Lies, which begins its fifth season this Sunday night, in the midst of the market crash in 2008 and the Occupy Wall Street movement that followed. He loved the book of the same name by Martin Kihn, which shined a bright light on the insider world of corporate consultants, and pitched it as a dark comedy to Showtime. That Cheadle was involved didn't hurt.

"I was honestly shocked that Don was going to do a TV show—and do our TV show," Carnahan admits. "We were incredibly lucky to start with him and then build the cast around him. But having Don involved meant that the acting was going to be at a whole other level." But Carnahan knew that Cheadle's involvement also raised the stakes. "As soon as he was involved I thought, 'OK, we better write good stuff,'" he says. "'This shit better be good, because he's going to just shred whatever we give him.' Then, when he and Kristen [Bell] got together, and we started watching them together, it was just amazing."

For Kristen Bell, a highly respected actress in her own right with a rabid fan base from her days playing the titular character on Veronica Mars, working with Cheadle was the chance of a lifetime—and the subject matter was icing on the cake. "Don Cheadle is a king," Bell tells me without hesitation when I ask about working with the Oscar nominee. "There's no other way to say it. He's such an emotionally connected person, despite the fact that he's fairly quiet in real life. He cares a ton about the stories that he tells. I think that's evident in his body of work."

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But it's not just her colleague that continues to fuel her interest in her own show. "Really, I love that the topic is this unexplored, taboo, dirty territory of the underbelly of the business world, which is, in its simplest form, greed," Bell says of House of Lies' subject matter, which gives room for intriguing plots and complicated characters. "Rarely do our characters struggle with any sort of a moral compass. We have a whip-smart writing team who keep the character interaction emotionally resonant and interesting within this backdrop of exploring this dirty business, which is good because I knew nothing about consulting prior to the show. These are scenes that take place behind closed doors. It happens within our political system. It happens with every business that exists. How to market yourself correctly. How to increase your bottom line. How to improve your brand. At all costs—at any cost."

For Cheadle—a diehard fan of Monty Python, and whose Marty Kaan is as cold and cut-throat as any character on screen—the idea that he could help shine a bright light on corporate culture in such a subversive way was too good to pass up. "I think the show is way funnier than it has been even before," he says of the new season. "But at the same time we're the victims. We're the kill! The stories we deal with in the show will make the news, maybe for a second, and people will focus in on it and say, 'That's horrible!' And then Donald Trump will say something and no one is paying attention to anything anymore."

The tone of House of Lies might be darkly comic, but its premise is rooted in the very real, cut-throat world of American business—which has, in turn, influenced the culture at large. "The show came about at a moment in time where the brightest light was being shone on these kinds of vulturistic, money-theistic, bottom-line, win-at-any-cost, sharky, take-advantage-of-everybody dudes," Cheadle says. "It was just in the zeitgeist. I'd never really thought about what it was that management consulting was and what these guys did. I hadn't seen a project like it, and I definitely hadn't been asked to be a part of a project like it. So that was a challenge, but I also believe it was an important story to tell, especially in the way we tell it."

The rest of the cast rounds out the lighter tones of the show, particularly Ben Schwartz, who plays the striving, completely dysfunctional Clyde Oberhalt, and whose subversive humor has been on display in his portrayal of Jean-Ralphio Saperstein on Parks and Recreation as well as on his website, Rejected Jokes. "[When] I got a call about playing Clyde, I immediately, really wanted to do it," he says. "I knew I would get to be so dark in it. And I really loved the idea of playing with drama and mixing it with comedy. The idea that the script was great, and that Don Cheadle was the lead was just incredible." Schwartz also expresses his delight at playing alongside the cast at large, who together have become a family of sorts. "You get cast and don't even think about it, but you spend so much of your life with people on a show like this," he says. "We've become really tight, and I think, especially in this season, with all of us back together for so many of the scenes, it's made the show even more unique and special."

Esquire is pleased to present an exclusive clip from the upcoming season of House Of Lies on Showtime.

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"I think we were smart in that way, to pull everybody in opposite directions a little bit for a few seasons," Cheadle agrees. "Because now that we've come back together, it's like fresh air. It feels like a comedy troupe: we all know who we are, and we know what beats to play and how to bounce things off of each other. [It's like] the four of us in the band, and everyone's getting different solos."

"This show has never wanted to be sentimental," says Josh Lawson, the Australian actor who plays Doug Guggenheim. "But what I love about the show is those sharp edges. The world we are dealing with really requires people to be bastards, I think, in order to be successful. And my character is a bastard, but he's a different kind of bastard. He's completely superior. He's a narcissist. He's arrogant. But I think his saving grace is that he genuinely wants to be liked." The balance of the ruthlessness and the humor—particularly in Doug—is the perfect combination that makes House of Lies work."Part of the comedy comes from the fact that he refuses to believe that people actually don't like him," Lawson explains. "He's immune or impervious to the relentless insults he gets. He refuses to accept reality. So I think the reason people who follow the show both hate him and love him at the same time is because they feel sorry for him. You really do feel sorry for the guy. In a lot of ways it's staggering he's made it as far as he has."

As for the now-historic notion of filming in Cuba, which until recently was under a 50-plus year trade embargo with the United States, everyone involved agrees it was worth the aggravation.

"It was challenging," Cheadle admits, "but the people were great, and the local crew was amazing. Sometimes, like in Cuba, you are filming in a place, and it's great because your reactions are pure and real and you're in a place where your mind's really blown. You don't have to pretend like anything's happening. You're really there with these doe eyes looking at everything and taking in this brand new experience."

"We were told about the possibility of Cuba right at the beginning of the season," Bell says. "Our production team honestly worked tirelessly, harder than I'd ever seen anybody work, to get us there. We wanted to cross that finish line of being a show that had historical significance as a first American production to shoot there. But not only did they have to figure out how to get everyone there to scout in Cuba, we had to comply with the Cuban government to make sure that everything we were showing and saying was approved—and we had to run everything by our State Department. It was unchartered territory." The significance isn't lost on the cast, especially for Bell. "In December last year, our production team was on the first direct flight from LA to Cuba since things were shut down," she says. "It's exhausting to even think about, because it was such a feat."

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"In terms of the people I worked with in Cuba, they just want the whole embargo thing to be over," Carnahan explains of his experience shooting in the country. "The Cubans I dealt with every day don't really talk about politics at all. They were just very excited we were there. But certainly from my tiny perspective it was a big deal. For me, at least within the show, it was kind of an apotheosis—a moment of culmination. And Cuba was so beautiful and so romantic. The place itself is just dripping in romance and exoticism."

"On the flip side of it, we were also getting to know what the challenges were for the people that lived there and what they were and had been experiencing," Cheadle says. "The struggle was also illuminating. We were happy to be a company there that was hopefully starting a process that would continue, where the people there would have an opportunity to better their lives through some kind of an exchange, because it's desperately needed. They don't need us to come over and supplant their culture or graft some American ideology on top of them or anything like that, but the people definitely need an infusion of something. Everyone's highly trained, and artists are classically trained in the arts. Everyone bought paintings because the art is just amazing. The guy who comes to your door and may be giving you more towels is probably a surgeon, but he has to work in the hotel because he's making more money off tips than he makes being a surgeon. So the people need the opportunity to better their lives."

As for any hints about what's in the storyline that attracts the cast to Cuba, everyone involved is keeping their lips shut relatively tight—though Bell offers some hints.

"Well, what's bigger than consulting for one of the biggest corporations in America? What's bigger than consulting for a global corporation? Consulting for a country," Bell says, slyly. "We essentially merged the two, and we have a client who wants to get their hands on Cuba now that some restraints have been lifted. We decide to explore their options and make the country theirs—viable for their business." Like in the show's previous four seasons, the art was imitating life. "Obviously there are other people trying to do it, too," she continues. "That was the funny part: We knew it was actually happening in buildings all around us. There were currently Americans and other businesspeople associated with America there sniffing around the country."

"That's why they're there," Cheadle says, in agreement. "They smell blood in the water. But it's not as easy as all that. It's like my great-grandmother used to say: It's more than a notion."

Jeff Slate Jeff Slate is a New York City-based songwriter and journalist who has contributed music and culture articles to Esquire since 2013.

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