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.

However, everything changed when Clint Eastwood decided to use "The First Time Ever I Saw Your Face" in a pivotal love scene in Play Misty for Me (1971). The song was released as a single in February 1972 and skyrocketed to No. 1, spending six weeks atop the Billboard Hot 100.

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Roberta Flack and Clint Eastwood’s Deal

In a 2012 interview with The Daytona Beach News-Journal, Flack recalled her surprise when Eastwood personally called her:

"I’m in my house in Virginia. My mom was living with me at the time. The phone rings and she said, ‘Roberta, it’s Clint Eastwood.’ I thought somebody was playing a joke," she said.

"He really surprised me. I didn’t faint but I came pretty close because I mean, this was a big thing. The conversation went like this (imitates Eastwood’s voice): ‘I’d like to use your song in this movie I’m doing. It’s called Play Misty for Me. It’s about a disc jockey, and it has a lot of music in it. I’d use it in the only part of the movie where there’s absolute love.’

"I said OK. We discussed the money. Of course, I was shocked. I gulped and said OK. He said, ‘Anything else?’ And I said, ‘I want to do it over again. It’s too slow.’ He said, ‘No, it’s not.'"

Flack later recorded "This Side of Forever," which played over the closing credits of Eastwood’s Sudden Impact (1983).

A Career of Timeless Hits

After Quiet Fire (1971) and Roberta Flack & Donny Hathaway (1972), Flack recorded Killing Me Softly (1973). The title track, originally recorded by Lori Lieberman, became one of Flack’s most enduring songs.

In 1975, she released Feel Like Makin’ Love. Its title track made her the first female vocalist since the 1940s to top the charts for three consecutive years. In 1977, Blue Lights in the Basement featured another hit duet with Hathaway, "The Closer I Get to You," which peaked at No. 2. Hathaway tragically died by suicide in 1979, on a day he and Flack were scheduled to record together.

During the 1980s, she toured with Peabo Bryson, and their duet "Tonight, I Celebrate My Love" became a Top 20 hit in 1983. She later collaborated with Maxi Priest on "Set the Night to Music," which reached No. 6 in 1991. Flack also frequently recorded with Luther Vandross.

Her final album, Let It Be Roberta: Roberta Flack Sings the Beatles, was released in 2012.

Actress, Author, and Philanthropist

Flack expanded her talents beyond music. She performed "Together Through the Years," the theme song for The Hogan Family (1986-91), and contributed to the Bustin’ Loose (1981) soundtrack. She also sang in The Wiz (1978) choir.

She was married to bassist Steve Novosel from 1965 until their 1972 divorce. During the 1980s, she lived in The Dakota in New York, where her neighbors included John Lennon and Yoko Ono. Their son, Sean Lennon, affectionately called her "Aunt Roberta."

In November 2022, the documentary Roberta premiered at the DOC NYC film festival. A few months later, in January 2023, she co-authored a children’s book, The Green Piano: How Little Me Found Music.

Roberta Flack’s remarkable career left an indelible mark on the music industry, inspiring generations of artists and fans alike.