Kaan's presence in Cuba -- or rather that of actor Don Cheadle, who plays Kaan, and the team behind the "House of Lies" show -- is a first for TV and for diplomacy.
They could also be the first in a line of TV and movie crews leaving Hollywood for Havana.
The plot of Showtime's "House of Lies" follows a team of rapaciously cutthroat management consultants, led by Cheadle's Kaan, who lie and cheat their way to big paydays.
So what brought these wannabe masters of the universe to Cuba, a country that in real life is just now beginning to open to foreign investment?
"(Kaan) is at the nexus of where he wants to be," Cheadle told CNN between scenes on the last day of the shoot in Havana. "The most upside possible if he gets in on the ground floor. Not just for Marty Kaan but all the Marty Kaans in the world. This may be ground zero, for better or worse."
Titled "No es facil," a popular Cuban saying that translates to "It ain't easy," the Cuban episode centers on the team's efforts to capitalize on Cuba's emerging market. It doesn't go according to plan.
"They are just going to come in and rape and pillage and eat the fruit and have it run down their faces," said "House of Lies" creator and executive producer Matthew Carnahan. "That's the plan. They are going to take Cuba and strip mine it. And Cuba, of course, is not up for that."
Until recently, Cuba was off limits not only to U.S. film crews, but also to American citizens.
For decades after Fidel Castro's 1959 revolution, most Americans weren't welcome in Cuba, and the U.S. trade embargo threatened hefty fines for those who did find a way visit the off-limits island.
The Cuba that Americans saw in movie theaters and on their televisions was usually a stand-in. The Havana scenes in the 1974 classic "The Godfather Part II," where Michael confronts his traitorous brother Fredo, were actually filmed in the Dominican Republic.
In the 2006 movie "Miami Vice," Sonny Crockett jet boats to Cuba to drink mojitos -- but the action was really shot in Uruguay.
In "GoldenEye" and "Die Another Day," James Bond fights supervillains in Cuba. In reality, Puerto Rico and Spain stood in for the island.
But with the resumption of U.S.-Cuban diplomatic relations
last summer, a loosening of restrictions has led to a surge in U.S. visitors.
While the U.S. trade embargo remains in place, a more relaxed attitude toward Cuba has encouraged film and TV crews to attempt to shoot on the island.
In addition to "House of Lies," producers of the next installment of the "Fast & Furious" franchise and a forthcoming Starz series called "Santeria" have expressed an interest in shooting in Cuba.
Despite the newfound buzz, it's unlikely that Cuba will become a favorite location for Hollywood.
Bob Yari, the director of "Papa," a soon-to-be-released film on Ernest Hemingway that was shot in Cuba, said: "It was quite difficult. There's a lack of infrastructure, facilities and equipment.
"They have great crews but they are just not used to the pace of American filmmaking. In a communist country, people aren't really in a rush to do anything."
Producers will still have to run a gauntlet of U.S. government red tape, Cuban censors and logistical issues -- like the fact that most American credit cards and cell phones don't work in Cuba.
"We are the first people looking for these approvals, we are the first people doing transactions this way," said "House of Lies" executive producer Jessika Borsiczky. "Asking our State Department and the Cubans to relate to each other over something like this, I feel a little bit like a pioneer. It's exciting."
"House of Lies" producers say they employed a Cuban crew of 120 people and that by the end of the weeklong shoot, the Americans and the Cubans worked as if they had been doing the show together for years.
While the still-threadbare island may not have been able to provide many Hollywood-style perks, the Cuban crew offered the Americans trays of sugary coffee and croquetas, savory fritters, between scenes.
And there was no substitute for shooting on the bustling, storied streets of Old Havana, the cast and crew said.
Cheadle added: "It's definitely so cinematic, the places to shoot are so scenic. You would hope there would be more crews here, if that works for the governments. It's a place that deserves to be brought onto the world stage."