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Yulier P. learned that the police were keeping track of his street art when he received a citation at his house, directing him to present himself for una entrevista: an interview. Fabián, another street artist, says the same news arrived in a letter ordering him to pay a $40 fine—the equivalent of eight weeks' salary for the average Cuban—or else serve a year in prison. With help from a friend, Fabián paid. Yulier went to the entrevista, taking with him a copy of the Cuban constitution. For two hours, an officer interrogated him. Did Yulier oppose the Revolution? Why hadn't he gone through official channels before creating public art? Yulier responded that he hadn't broken any law and pointed to constitutional clauses guaranteeing his right to create art so long as it didn't oppose the Revolution. In the end, neither he nor Fabián was arrested, an outcome that suggests a growing acceptance of political art in Cuba.

In Havana, the art of Yulier P. and Fabián is nearly ubiquitous. It appears in alleys, residential streets, major thoroughfares, and on the city's many ruins. The roofless husk of an abandoned theater in the Centro neighborhood has become a sunlit gallery where a red lupine creature with hanging breasts—Yulier's invention—extends its only arm in supplication, like a beggar; on the opposing wall, a life-size figure in a balaclava—Fabián's go-to character—lifts his hands and eyes in a motion of entreaty that, if not for its air of futility, might be priestly.

The art covering walls from Habana Vieja to Vedado reflects the concerns of a younger generation of Cubans ever more connected to the world outside, even while they struggle to see a future in their own country. Yet both Yulier and Fabián acknowledge that, 10 years ago, their art wouldn't have been possible. Unlike many political artists in Cuba's past, neither has been jailed since they began painting publicly over the last three years, though the laws remain the same (and are, in theory, similar to many state and city ordinances prohibiting vandalism in the United States). The multiplying paintings across Havana indicate that some of the youth feel more at ease, or at least more intent on, speaking out, and hint at a new attitude of measured tolerance on the part of the Cuban leadership toward artists who are not perceived as threats.

"Raúl Castro is engaged in a PR campaign to project an image of change in Cuba to attract less criticism and more foreign investment," Sebastian Arcos, associate director of the Cuban Research Institute, told Pacific Standard in an email—though he stressed that, since Raúl Castro became president of Cuba in 2008, there haven't been fundamental reforms so much as "what dissidents call 'Cambio Fraude' [fraudulent change].... Any serious political threat is still handled quickly and harshly." Still, both Arcos and Brian Latell, the author of three books on Cuba, agree that Fidel Castro would never have allowed any such subversive art. Latell has long held that Raúl Castro has a vision for Cuba that differs significantly from that of his brother, a vision that is now possible after Fidel's death. Latell believes that the Cuban leadership doesn't truly fear political upheaval, but that they are—speaking broadly—"very worried that the youth are unhappy, that they're alienated, and that they don't believe in the Revolution."

"What we have here," Yulier P. says, "is the worst of socialism and the worst of capitalism." A 27-year-old from a small town in the island's interior, he is heavily tattooed and bald and has a black beard, resembling—with his frequent smiles—a good-humored pirate. After high school, he moved to Havana for an accounting course but dropped out after a year. Disturbed by Cuba's extreme poverty and the vast divide between the rich and poor, he resolved to use art to denounce those in power, from the government to the private sector. "A revolutionary socialist program, after 58 years, should have solved these problems."

When he decided to begin painting in the street, Yulier struggled with his fear of the police. To get used to working in the open, he accompanied an experienced graffiti artist, and gradually became accustomed to creating his art during the day, under the gazes of police and passers-by. He soon established himself as one of the most prolific street artists in Havana, signing his tableaus Yulier P. He often painted in underprivileged neighborhoods, on walls so deeply weathered that his images instantly resembled ancient frescoes. He wanted to remind the people who lived there that it was possible to have a voice and to express their struggles. "Cubans have been indoctrinated to fear speaking out. I don't understand this, since this is a socialist project, created by the people."

His characters appear as though through a filter that reveals their raw emotion—hairless figures often lunar in their pallor and starkness. One is gagged and shackled. Some scream. Others have no mouths in their faces, only in their stomachs: robbed of language while their hunger speaks. There is the recurring creature with many breasts—an evocation of Cuba, struggling to feed her children as she extends a long hand seeking charity. During his first entrevista, Yulier told the police that, by painting on damaged property, he actually increased the city's beauty rather than doing harm.

After Yulier P., Fabián is perhaps the most prolific street artist in Havana. A 20-year-old from Havana's largely Afro-Cuban Centro neighborhood, he is also heavily tattooed. But unlike Yulier—who, despite his rebellious look, comes across as the responsible owner of a small business—Fabián has the aura of a rock star. When he walks through the city, young women occasionally hurry into the street to speak to him, and, at the art collective, he sometimes has an entourage—young people sitting around him as he lounges on his breaks from painting to drink beer and smoke cigarettes with a languid cool. His expression of hip detachment matches his style and outfit—his pierced septum, the bleached tuft at the front of his afro, the white cord of his headphones running through an enlarged hole in his right earlobe; the yellow socks printed with pot leaves, the red Converse knock-offs shredded from skateboarding, and the skateboard itself, painted with a vampire licking a blood-red ice cream cone.

After high school, Fabián briefly trained to be a plumber, before turning to art and studying at the local collective, where Yulier, among others, mentored him. In 2016, Fabián began painting his masked figure in the streets and has now done so more than 100 times. He calls the character Supermalo—Superevil. The inspiration came to him when he was listening to music online and saw the album art for Stolen Youth by the American rappers Vince Staples and Mac Miller: a drawing of three babies, one black, one brown, and one white, each wearing a diaper and a balaclava. Though Fabián's life-size or larger images are often cartoonish, Supermalo—who in another country might become a young man's two-dimensional gangster fantasy—rarely conveys machismo or strength. On Calle Neptuno, a major thoroughfare, a halo hovers above Supermalo's head as he stares down sadly at a single flower. On a touristy street in the Old City, he wears a superhero costume, complete with a cape and the letters SM emblazoned on his chest, while, in a thought bubble, he dreams of a fried egg—a nod to the heroism of those who carry out the small but challenging tasks required each day for survival in Cuba. In another painting, this one on a metal door, Supermalo is a homeless person sleeping in a doorway. On a wall across from a church, he appears as Jesus Christ. In many places, he simply holds his head in confusion.

"Here in Cuba," Fabián says, "when there are personal or social problems ... we have to speak while staying hidden. Everyone has a mask. Everyone wants to speak. I am speaking for everyone."

Next to each painting of Supermalo is Fabián's signature: 2+2=5, a direct reference to the passage in 1984, where George Orwell writes: "In the end the Party would announce that two and two made five, and you would have to believe it." The signature has been taken up by Fabián's fans (and more recently by Yulier P.) and now appears throughout the city: stenciled, scratched with keys on walls next to messages of love, spray-painted in large, bubbly print.

There remain certain lines that Cuban street artists cannot cross. The graffitist Danilo Maldonado Machado—who goes by the name El Sexto, meaning The Sixth—has been repeatedly incarcerated over the past three years. For a piece of performance art, he painted the names Fidel and Raúl on two pigs (another reference to Orwell, this time to Animal Farm). His imprisonment is a reminder that, while some art is tolerated, the Cuban leadership draws the line at direct attacks against the Revolution and negative representations of the Castro brothers. Artists around the world have paid tribute to Machado, and his supporters have complained widely that the Cuban government listed his offense as desacato—contempt—without ever formally charging him or allowing him a trial. (Given Machado's links to opposition groups, and his more direct confrontation with the Cuban government, it is difficult to compare his situation to those of Yulier and Fabián, or to judge whether the international attention around his case has in any way influenced why they haven't been incarcerated.)

Despite censorship, Cuban art has a vibrant history of social and political critique, Michael Bustamante, assistant professor of history at Florida International University, explains: "Cuban officials generally do not slap long-term jail sentences on artistic critics—preferring dissuasion, avoidance, denial of exhibition space, and sometimes the partial self-censorship that comes in response, to more drastic measures that might drum up international attention. Art, in fact, continues to be a realm in which substantial, if delimited, social critiques are possible."

Neither Yulier nor Fabián dismisses socialism or romanticizes the U.S. Like many in their generation, they understand the failings and abuses of both, and even as they want change in Cuba, they see their options dwindling. Normalization with the U.S. has led to relatively few business deals, the Cuban economy is in recession, and the Obama administration's repeal of the Wet Foot, Dry Foot Policy—which offered expedited permanent, legal residency to Cuban migrants who reached American shores—in January of 2017 put an end to two years of the largest outmigration since the early 1980s. Both Yulier and Fabián are often online, communicating with street artists and fans and sharing their work on Instagram. Yulier's account (@yuliergraffiticuba) shows his screaming, tormented characters. The poses he strikes in the photographs are often gangsterish: a bandana on his head, his tattoos exposed, or his middle finger lifted. In one photo, he wears a T-shirt that reads if you pay peanuts, you get monkeys, and in another respeto al arte urbano.

Fabián's account (@ttttteoe) is more aggressive. Supermalo is on his knees, bowing to a wall, or naked in the posture of Michelangelo's David, with a fried egg hiding his genitals. Or he points up at a sticker that reads Fuck Donald Trump. In Fabián's profile picture, Supermalo is painted on a Cuban flag duct-taped to the large numerals of 2+2=5 on a wall. He jabs his index finger at the viewer like a thuggish Uncle Sam. Next to him, Fabián stands shirtless, wearing a Guy Fawkes mask.

"Our commander-in-chief, Fidel Castro—now deceased—said that the greatest revolutionary is he who expresses the truth," Fabián explains. "That means I am a revolutionary. The counter-revolutionaries are the ones who want to stop me."

A version of this story originally appeared in the October 2017 issue of Pacific Standard.