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Iconic singer and pianist Roberta Flack, who made Grammy history with her unforgettable No. 1 hits "The First Time Ever I Saw Your Face" and "Killing Me Softly With His Song," passed away on Monday in New York at the age of 88.

"We are heartbroken that the glorious Roberta Flack passed away this morning," read a statement from her representative. "She died peacefully surrounded by her family. Roberta broke boundaries and records. She was also a proud educator."

Flack suffered a stroke in 2016 and retired from performing in 2018. She was diagnosed with ALS, also known as Lou Gehrig’s disease, in 2022.

Grammy-Winning Legacy

Flack’s remarkable career saw her win multiple Grammy Awards. She received a second Grammy in 1973 for "Where Is the Love," her duet with college friend and frequent collaborator, the late Donny Hathaway. The song peaked at No. 5 on the charts.

Her smash hit "Killing Me Softly" earned Flack a Grammy for Best Pop Vocal Performance and spent five weeks at No. 1 in 1973. She followed this success by topping the charts again in 1974 with "Feel Like Makin’ Love," which earned her three of her 14 career Grammy nominations.

In 2020, she was honored with a Grammy Lifetime Achievement Award.

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Early Life and Musical Beginnings

Roberta Cleopatra Flack was born on February 10, 1937, in Black Mountain, North Carolina, and raised in Arlington, Virginia.

Her father, Laron, was a draftsman for the Veterans Administration, while her mother, Irene, was a church organist.

Flack’s prodigious musical talent was evident early on. She took classical piano lessons and, at 13, performed the complete score of Handel’s "Messiah" for her church choir.

She attended Stevens Elementary School in Washington, Hoffman-Boston High School in Arlington, and at just 15, won a full music scholarship to Howard University.

At 19, Flack left graduate school at Howard following her father’s passing. Then she became an English teacher in Farmville, North Carolina, and Washington, D.C.

She gave music lessons on the side and performed at nightclubs, including Mr. Henry’s in Capitol Hill, where jazz legend Les McCann discovered her in 1968. He helped her secure a deal with Atlantic Records.

"Her voice touched, tapped, trapped, and kicked every emotion I’ve ever known," McCann wrote in the liner notes for Flack’s debut album, First Take. "I laughed, cried, and screamed for more … she alone had the voice."

Rise to Stardom

Flack’s debut album, First Take (1969), and its follow-up, Chapter Two (1970), initially did not garner much attention.