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Paul Simon might be New York's quintessential songwriter: He was born in Jersey, he's worked with people from Queens to Ghana, and though he changes styles radically and frequently, his favorite subject remains his own experience. Simon, along with Art Garfunkel, sent his first song to the Library of Congress in 1956, at 14 years old. On April 1, he begins "Love in Hard Times," a month-long performance residency at the Brooklyn Academy of Music that will feature work from the entirety of his 52-year career.

The BAM project is divided into three different sets of performances. "Songs From The Capeman," which runs from April 1 to 6, will feature the music from his foray into theater, with guest performances by Little Anthony and the Imperials, Oscar Hernández and the Spanish Harlem Orchestra, and salsa vocalist Ray de la Paz, among others. The second set, "Under African Skies" (April 9-13), will spotlight the African, Brazilian—and Afro-Brazilian—styles Simon focused on for 1986's Graceland and 1990's The Rhythm of the Saints. Guests include Hugh Masekela, David Byrne, and Milton Nascimento (who sang on Saints' "Spirit Voices"). The last, "American Tunes" (April 23-27), will have help from Olu Dara and Grizzly Bear (among others), and will cover everything in the cracks, from the po-faced, turtlenecked Simon of the mid-'60s through the relaxed-dad musings of 2006's Surprise.

Opening with songs from The Capeman is a bold move. The 1998 musical—a collaboration between Simon and Nobel laureate Derek Walcott about the life and incarceration of Puerto Rican gang member Salvador Agron for two 1959 murders—cost $11 million, ran less than three months, and is regarded with consensus to be Simon's greatest misstep as an artist. His choice to put it front and center is, then, humorously obstinate in the way we hope all Great Artists are—as if he believes himself working in our best interest by forcing us to admit that The Capeman is good. The music—a jigsaw of doo-wop, early rock & roll, and Latin American pop—isn't really all bad, but even removed from the shadow of the show's failure, it doesn't seem altogether worth revisiting. It's a great opportunity to hear him attempt to talk jive and say "fuck" several times. But instead of sounding inspired by the story and its underlying themes of cross-cultural and racial conflict of '50s New York, Simon sounds burdened. He lets loose disjointed historical details, presumably because he thinks it legitimizes the narrative. His subjects' shoes don't fit him, but he tries to cram into them anyway, to sing through their voices. Every time he uses the word "I" in The Capeman, I wince a little.

Part of it's that Simon had already dealt with these kinds of cultural tensions in more compelling ways. Graceland, made in South Africa in 1986 with local musicians, still sounds relevant, both as an artistic document problematized by time and place, and as a great album. During its making, Simon was under tremendous scrutiny for what plenty of people characterized as an insensitivity to the complexities of apartheid—a political nightmare that he had suspiciously little public comment on despite his indulgence in South African music.

But, with the exception of Graceland's embarrassing "Under African Skies"—where he sounds like a Jewish New Yorker fussing over cradle-of-civilization mythology—it's Simon's relative indifference to South Africa that saves Graceland. The album is a testament to the universal appeal of the music itself, rather than a forced political statement on a subject he isn't moved to discuss—and one he probably doesn't totally understand. The Rhythm of the Saints is a little like Graceland, Again, with Brazil standing in for South Africa. While it produced a couple of fantastic songs—"The Obvious Child," "Can't Run But"—its chronological relation to Graceland and slip in quality will always make it feel like an afterthought.

Joe Melillo, BAM's executive producer, has been working since 1999 to solidify this project. He explains that the reason for dividing the month into three sections is to offer "the ability to be immersed in this material—be it from Brazil, South Africa, or New York." But naming the last segment "American Tunes" is a strange way to differentiate any one set of Simon's music. Aren't they all? Even Simon's more nominally "American" first couple of albums—the moody, remarkable Paul Simon and the far less moody and slightly less remarkable There Goes Rhymin' Simon—featured reggae facsimilies ("Mother and Child Reunion"), Brazilia-lite (the buoyant, ever-inscrutable "Me and Julio Down by the Schoolyard"), and Stéphane Grappelli violin runs ("Hobo's Blues"). Simon's parents were Hungarian immigrants. He wrote a soft-rock song about Mardi Gras, an exemplary mongrel of American culture. He wrote about the surrealist painter René Magritte and his wife dancing to the Penguins and the Moonglows; he blanched gospel to sing about being a mama's boy ("Love Me Like a Rock"); and he helped invent a strain of affable pop music so variously influenced it ends up sounding orphaned, traceless ("Slip Slidin' Away," "Kodachrome," "50 Ways to Leave Your Lover").

Simon once said he thought "Graceland" was his best song. It probably is. When he first heard South African music, he was floored; when he found out where it was from, he remembers wishing it had been from anywhere else. "Graceland" tells the story of a divorced man dragging his son on a journey of self-discovery through the slave-state home of America's most overexposed pop figure. By setting that vision to the bounce of an oppressed people, Simon was able to transpose his complicated passion for South African music into a story about muted redemption. In 1978's "The Big Country," the Talking Heads weighed the same subjects—the urban perception of purity in the Middle-western and Southern states, the allure of their simplicity—but, tellingly, placed its narrator on an airplane. And while David Byrne's characters might never sound as pitiable as Simon's, Simon's would never be so disengaged. In his career's weaker moments—see the bulk of The Capeman—he tries very hard to appear weighed down by the plight and place of his characters, but in his best—"Graceland"—he sounds genuinely upset. For someone so cherished, it's remarkable how little Paul Simon actually smiles.

When asked why he wanted to celebrate Simon's career, Melillo responded, "I think he really does have something to say as an artist in our lives." He's not wrong, of course, but it's a perfunctory remark. What has Paul Simon said about our lives? In certain ways, it's remarkable how popular he's become. He's recorded snappy hits about how terrifying it is to get old and how painful it is to be lonely. But to exalt him for subverting traditional pop-song subjects misses the depth of his impact. He's as subversive as a public park. Paul Simon didn't have to smuggle the dark and truly heartbreaking into pop music—they're sentiments he helped recast as essential to the form. To doubt whether or not the general public feels the painful undercurrents of a song like "Graceland" is condescension at its ugliest. His popularity isn't an accident or a coup, but a reminder that the stories most difficult to hear are usually the ones we end up holding onto the longest.