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Brazilian singer-songwriter Negro Leo is dedicated to freedom, both musical and political, and his first-ever performance in the United States is, characteristically, a joyous train wreck. His band of friends and fellow travelers only had time for one practice session before this free gig in a small hall at Lincoln Center in August of 2018, and you can kind of tell. The audience, seated in folding chairs, is a mix of enthusiasts and passersby; one woman next to me says she's unsure what language Leo is singing in. (That would be Portuguese.) But the band makes no concessions to neophytes. Songs start and stop seemingly at random, provoking confused, scattered applause before the group launches into an approximation of a bossa nova record that's been smashed with a hammer. On guitar, Guilherme Monteiro vacillates between feedback freakout and punk crunch, while Chris Eddleton sets up an unholy clatter on the drums and Micah Gaugh blows into two saxophones at once, unleashing a barrage of skronks.

Leo himself grins maniacally, crooning and scatting like a chipmunk. He bops and weaves and thrashes his trademark flyaway curls with such enthusiasm that his glasses fall off repeatedly. "Play more aggressive this time!" he shouts to the band, then wanders out into the audience, sans microphone or guitar, still yelling encouragement to the players. During much of the set, his five-year-old daughter dances in the aisle and chants along, blowing kisses to her dad and radiating joy.

Improvisation and spontaneity are central to Leo's art. Along with his wife, the singer Ava Rocha, Leo, born Leonardo Gonçalves, has been part of a niche but vibrant experimental music scene in Rio, focused on the Quintavant record label, and often played for small but passionate audiences at the club Audio Rebel. His sound is influenced by free jazz, New Wave, and Brazilian Tropicália, with its mix of psychedelia, bossa nova, and anarchic parody. Tropicália was, in part, a reaction to the authoritarian Brazilian regime that lasted from the 1960s until 1985; free jazz was an assertion of black genius and liberation. Leo's music, too, with its joyous chaos, is a playful refutation of the strictures that characterize the life of poor people in his home country.

Leo's varied influences, and his openness to the unexpected, represent a social and cultural stance, as well as a musical one: He celebrates Brazil's messiness and its jagged edges. His stage name, Negro Leo, is, in part, a childhood nickname, but it's also a political choice. "In Brazil," he says, "the word 'negro' has been used for black activists since forever." Brazil is extremely color-conscious; the darker your skin, the more discrimination you tend to face. By naming himself Negro, Leo proudly claims the stigma associated with being black, aligning his art with the oppressed people of his country. "In Brazil, we need to become black," Leo says, advocating a radical solidarity with the country's least fortunate. "When I say we, I mean the nation. And when I say black, I mean all people not white."

Leo has been particularly inspired by what he calls lek culture, or "the culture of impoverished youth that ... resists every situation with pride and joy," as the press release from his 2017 album Action Lekking puts it. Lek in carioca, or Rio de Janeiro slang, means "boy" or "dude," Leo explains to me in his hotel room across from Lincoln Center after the show. He responds to questions in a mix of English and Portuguese, with loose translations provided by Henry Schroy, who played bass at the Lincoln gig, and New York-based American-Brazilian singer Gabriela Riley.

On stage and in person, Leo is irrepressible. As we talk, he launches into the occasional unaccompanied song, wailing snatches from the work of Jorge Ben, the great Brazilian musician who, in songs like "Meus Filhus, Meus Tesouro" ("My Children, My Treasure"), gave voice to the perspective of Brazil's poor. Leo also chants, "ah, le lekky lekky lekky lekky lekky lekky" from the big Brazilian hit song "Passinho Do Volante," which loosely means "The Steering-Wheel Step."

For Leo, singing for the lek is singing for the poor. Inequality in Brazil is massive; Leo explains that poor young people growing up in the favelas aren't even allowed to go into high-end stores, and that many of them only vaguely understand what air travel is, since they don't know anyone who's ever been on a plane. Racism and income segregation create a massive gap in the experiences of the affluent and the poor. "O brasil não viu o óbvio / Mulato vive / Vivo / Mulato morre," Leo sings with jazzy, frantic passion in his song "Mulato": "Brazil did not see the obvious. Mulatto lives / live / Mulatto dies." The song speaks to the invisibility of the black poor of Brazil, and how they live and die unseen.

In the 21st century, President Luiz Inácio "Lula" da Silva and his left-wing Workers' Party made unusually aggressive steps toward reducing Brazil's inequality, by increasing social spending and prioritizing the needs of the poor. The government wasn't perfect, Leo says—residents of the favelas still had open sewage flowing by their homes—but people felt their lives might be getting better. Singing about lek culture, for Leo, is an expression of that period of hope.

Then, in 2016, president Dilma Rousseff was impeached in what some observers called a right-wing coup. Money for the favelas dried up; social spending for health care and schools was frozen. "Where is everybody?" Leo asks in Portuguese. "Where are the intellectuals? Where are the anarchists? There's no power anymore within the people to go up against the government."

After our interview, things got even worse. In October, extreme right-wing candidate Jair Bolsonaro won Brazil's presidency.

As Leo tells me in his apartment, speaking English: "There's no more hope. Not anymore."

That's a bitter assessment. But onstage, Leo isn't quite so despairing. At the end of the performance, he stands alone before the band with his hand raised in something like supplication for a minute ... two minutes ... five minutes ... it seems to go on forever. The crowd dissolves into giggles and applause, lapses into awkward silence, and starts giggling again, before Leo unceremoniously stops, and the performance stumbles to an end. As in punk rock, the amateurism and uncertainty breaks down barriers between performer and audience. For Leo, we're all here together, trying to find our way. Leo's music is funny, uncomfortable, inspiring, and disarmingly vulnerable. Even in the face of Brazil's creeping authoritarianism and the systematic disenfranchisement of its poor and black residents, Negro Leo continues to celebrate the possibility of surprise, invention, and change.