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Roberta Flack, the veteran Grammy-winning soul and R&B vocalist who recorded massive hits with “The First Time Ever I Saw Your Face” and “Killing Me Softly with His Song,” died Monday at age 88. Elaine Schock, Flack’s representative, confirmed the singer’s death from cardiac arrest. “Roberta broke boundaries and records. She was also a proud educator,” a statement read. In 2022, Flack was diagnosed with amyotrophic lateral sclerosis (ALS) and lost her ability to sing. The disease, her rep said at the time, “has made it impossible to sing and not easy to speak.” “She sang reveries as much as exclamations, and yet her stillness electrified the soul. In time, the style she created became known as ‘quiet storm,'” journalist Mikal Gilmore wrote in a tribute accompanying the announcement of her death. “If Roberta Flack was unlike singers who came before her, there were many who would emulate her in her wake. In fact, her influence has never stopped reverberating. She was a woman who sang in a measured voice, but her measurements moved times and events as much as they moved hearts.” Born Feb. 10, 1939, in Asheville, North Carolina, Flack proved to be a piano prodigy, playing alongside the choir at her church and going on to earn a scholarship to study classical music at Howard University. For Flack, classical music was the foundation of her practice; even the music at the AME Church her family attended was more Handel and Bach than the high-energy gospel found in Baptist churches. “For the first three decades of my life, I lived in the world of classical music,” Flack told NPR in 2020. “I found in it wonderful melodies and harmonies that were the vehicles through which I could express myself.” After graduating from Howard, Flack planned to continue her studies, but her father’s death forced her to leave school and start a teaching career in her home state. She eventually began gigging in clubs in Washington, D.C., with the likes of Burt Bacharach and Johnny Mathis in attendance. As the buzz around her grew, Flack, at that point in her early thirties, was signed to Atlantic Records, which released her first album, First Take, in 1969. Flack recorded First Take over just 10 hours at Atlantic Studios in New York that February, working with a crack team of session players including bassist Ron Carter and guitarist Bucky Pizzarelli. The album found Flack interpreting an array of different songs from the protest song “Compared to What” (written by close collaborator Gene McDaniels) to “Angelitos Negros,” a ballad originally penned for the 1948 Mexican film of the same name. Flack also turned in what arguably became the definitive version of Leonard Cohen’s “Hey, That’s No Way to Say Goodbye.” While First Take would eventually assume its rightful place as a widely recognized masterpiece, success was not immediate. The first few singles failed to chart, and Flack quickly moved on to her next records, releasing Chapter Two in 1970 and Quiet Fire in 1971. She also linked up with friend and fellow Howard University student Donny Hathaway for a duets album, with the pair earning minor hits with contemporary pop standards like “You’ve Lost That Lovin’ Feelin'” and “You’ve Got a Friend.” But Flack’s real breakthrough came when Clint Eastwood used her meditative version of British folksinger Ewan MacColl’s “The First Time Ever I Saw Your Face” — originally recorded for First Take — in his 1971 film Play Misty for Me. The song shot to Number One and took First Take along with it, with the album eventually reaching Number One on the Billboard 200 in April 1972 nearly three years after its original release. Flack’s version of “The First Time Ever I Saw Your Face” would go on to win the Grammy for Record of the Year in 1973 (and she and Hathaway won Best Pop Vocal Performance by a Duo, Group or Chorus for “Where Is the Love” that year, too). Over the next few years, Flack’s sensuous voice and piano were ubiquitous on pop radio. Her version of “Killing Me Softly With His Song” hit Number One in 1973 and went on to win Record of the Year at the 1974 Grammys — making Flack the first artist to win the category two years in a row. She scored her third Number One single the following year with the friskier “Feel Like Makin’ Love.” And with Hathaway, Flack recorded some of the most beloved R&B duets of the era: “Where Is the Love” and “The Closer I Get to You.” While Flack helped pioneer the quiet storm R&B genre, her versatility as a performer and interpreter were unmatched as she incorporated elements of folk, rock, jazz, R&B, show tunes, and soul. “My music is inspired thought by thought, and feeling by feeling,” she once wrote. “Not note by note. I tell my own story in each song as honestly as I can in the hope that each person can hear it and feel their own story within those feelings.” Flack was also deeply involved in political movements of the post-Civil Rights era. She befriended Angela Davis and the Rev. Jesse Jackson, and she sang at Bob Dylan’s 1975 benefit concert for boxer Rubin “Hurricane” Carter, who’d been wrongfully convicted of murder. She was also a staunch supporter of gay rights: Her 1982 hit “Making Love” was recorded for the film of the same name about a married man coming to understand his homosexuality. Starting in the Eighties, Flack began to work at a steadier pace, but still found plenty of success with songs like 1983’s “Tonight, I Celebrate My Love” with Peabo Bryson, 1988’s “Oasis,” and 1991’s “Set the Night to Music” with Maxi Priest. Fittingly, for someone who once spent 10 years as a teacher, Flack was also known as a mentor to up-and-coming singers including Bryson, Luther Vandross, Marcus Miller, and Patti Austin. Later in life, Flack would help found the Roberta Flack School of Music to provide kids in the Bronx with free music education, while her Roberta Flack Foundation supported music education and animal welfare. Flack released her last full-length record, Let It Be Roberta — featuring interpretations of Beatles songs — in 2012, while in 2018 she recorded “Running” for the documentary 3100: Run and Become. Flack scored four Grammys alongside a Lifetime Achievement Award in 2020. “It was overwhelming and breathtaking to be there,” Flack said of receiving the Lifetime Achievement Award. “When I met those artists and so many others in person and heard from them that they were inspired by my music, I felt understood.”