It begins almost too quietly to be a hit. A soft piano figure, a voice that never rises above a murmur, and then the confession that has stopped listeners cold for half a century: a stranger on a stage, singing a song that seems to know everything about her. “Killing Me Softly with His Song” is not a song you shout along to. It is a song you lean toward, the way you lean toward someone telling you a secret. When Roberta Flack released it in January 1973, it became one of the biggest hits of the decade, won three Grammy Awards, and made her the first artist ever to win Record of the Year twice in a row. And the strangest thing about it is that it is, at heart, a song about listening to a song — a chain of one singer hearing another singer, and hearing herself, that stretches from a Los Angeles nightclub in 1971 to a hip-hop classic in 1996 and beyond.
To understand why the record mattered, you have to understand who Roberta Flack was when she found it. She was no overnight sensation, though the world would soon treat her like one. Born Roberta Cleopatra Flack on February 10, 1937, in Black Mountain, North Carolina, and raised in Arlington, Virginia, she was a child of musicians: her father was a Veterans Administration draftsman and her mother a church organist. She was a classical piano prodigy, playing the complete score of Handel’s Messiah for her church choir at thirteen, and she won a full musical scholarship to Howard University at just fifteen, majoring in music education. Her father’s sudden death cut short her graduate studies, and she went to work as a teacher, first in a segregated school district in Farmville, North Carolina, where she was the only music teacher for some 1,300 students from kindergarten through twelfth grade, and then for seven years in junior high schools in Washington, D.C.
By night, she was building a second life. She performed in Washington clubs, and her residency at Mr. Henry’s, a Capitol Hill nightclub, became the stuff of local legend. The owner, Henry Yaffe, was so taken with her that he converted an apartment above the club into a private studio known as the Roberta Flack Room. Her repertoire ran to some 600 songs, and her sets mixed gospel, soul, jazz, flamenco, and classical arrangements, all delivered in a voice of extraordinary restraint. Jazz pianist Les McCann heard her, arranged an audition with Atlantic Records, and in 1969 she recorded her debut album, First Take, in about ten hours of studio time. It was a critics’ favorite and a commercial slow burn. For two years, it waited for its moment.
That moment arrived, improbably, through a movie. Clint Eastwood, making his directorial debut with the 1971 thriller Play Misty for Me, heard Flack’s version of the Scottish folk ballad “The First Time Ever I Saw Your Face” — a song Ewan MacColl had written in 1957 for his wife, Peggy Seeger — while driving down a Los Angeles freeway, and he knew he needed it for the film’s love scene. Released as a single in February 1972, it spent six weeks at number one on the Billboard Hot 100, became the best-selling single of the year in America, and won Record of the Year and Song of the Year at the 1973 Grammy Awards. Flack, who had spent a decade teaching schoolchildren and singing in clubs, was suddenly, at thirty-five, one of the most famous voices in America. She needed a follow-up that could prove the first hit was no accident. She found it, as she found so many songs, by listening.
The song she found had already lived one quiet life. Its story begins in November 1971, when a twenty-year-old aspiring singer named Lori Lieberman went with her friend Michele Willens to see Don McLean perform at the Troubadour nightclub in West Hollywood. McLean’s “American Pie” was climbing the charts, but it was another song in his set, the haunting ballad “Empty Chairs,” that transfixed Lieberman. As McLean sang, she scribbled poetic notes on a paper napkin, trying to capture the uncanny feeling of a stranger on a stage reaching deep inside her and singing her own life back to her. Willens later confirmed that Lieberman started scribbling as soon as McLean began to sing. After the concert, Lieberman telephoned the veteran lyricist Norman Gimbel, with whom she was working, and read him her notes. Her description reminded Gimbel of a phrase already sitting in his idea notebook: “killing us softly with some blues,” a line he had borrowed from Julio Cortázar’s novel Hopscotch, published in English in 1966. Gimbel expanded Lieberman’s notes into full lyrics, and the composer Charles Fox set them to a faintly melancholy melody. Lieberman recorded the song in late 1971, and it was released as a single in 1972, produced by Gimbel and Fox. It did not chart.
There is a shadow over this part of the story that deserves to be told plainly. Lieberman received no songwriting credit on “Killing Me Softly with His Song.” Gimbel himself said in 1973 that her conversation had “fed me, inspired me, gave me some language and a choice of words,” and for years both men agreed with her account of the McLean concert. But around 1997, Fox and Gimbel changed their stories to downplay her role, and when Songfacts asked Fox about the McLean origin in 2010, he called it an “urban legend,” saying it “really didn’t happen that way.” The dispute has never been fully resolved, and it is part of the song’s history now: a song about a woman feeling exposed by a man’s song began with a young woman whose contribution was, in the end, written out of the credits. It is worth remembering her name when the chorus arrives.
Flack’s own discovery of the song is one of pop music’s great legends, and by her own account it is true in every detail. In 1972, on an American Airlines flight from Los Angeles back home to New York, she chose the in-flight audio program over the movie or a nap, and scanned the list of selections. One title stopped her cold. “The title, of course, smacked me in the face,” she later said. “I immediately pulled out some scratch paper, made musical staves [and then] play[ed] the song at least eight to ten times jotting down the melody that I heard.” It was Lieberman’s recording. When the plane landed, Flack immediately called Quincy Jones at his house and asked him how to meet Charles Fox. Two days later, she had the music.
She did not rush it into a studio. She rehearsed the song with her band at Bob Marley’s studio in Kingston, Jamaica, but did not record it. Then came the night that settled the matter. Later that year, opening for Marvin Gaye at the Greek Theatre in Los Angeles, she reached the end of her set and the audience demanded an encore. Gaye told her to sing another song. She sang “Killing Me Softly,” and the audience lost its mind. Gaye walked over, put his arm around her, and said, “Baby, don’t ever do that again live until you record it.” She took his advice.
Flack recorded the song on November 17, 1972, at Atlantic Studios in New York, with Joel Dorn producing and Flack herself arranging the track. Everything about the recording is a study in restraint. Where Lieberman’s version had been a folk-pop ballad, Flack slowed it down, stripped it back, and built it around her piano and a voice that seems to be singing directly into one listener’s ear. The arrangement breathes: a gentle guitar, a soft rhythm section, and above it all that voice, never pushing, never showing off, letting the lyric do the devastating work. It was, in a sense, the sound she had perfected over a decade at Mr. Henry’s — a singer who trusted quiet more than volume, and who knew that the most powerful thing a voice can do is sound as if it is telling the truth.
Released as a single in January 1973, “Killing Me Softly with His Song” climbed with startling speed. It debuted on the Billboard Hot 100 at number 54 on January 27, reached number one on February 24, and stayed at the top for five non-consecutive weeks — more weeks at number one than any other record that year. Billboard ranked it the number three song of 1973. It also topped the charts in Canada and Australia and reached number six in Britain. The album it led, Killing Me Softly, reached number three on the Billboard album chart, went double platinum, and was nominated for Album of the Year. At the Grammy Awards in March 1974, the song completed a historic sweep: Record of the Year and Best Female Pop Vocal Performance for Flack, and Song of the Year for Fox and Gimbel. The Record of the Year win made Flack the first artist in Grammy history to win that award in two consecutive years, following her 1973 win for “The First Time Ever I Saw Your Face.” She would remain the only solo artist to do so for nearly half a century, until Billie Eilish matched the feat. In 1999, the recording was inducted into the Grammy Hall of Fame.
What is it, finally, that keeps the song alive? Part of the answer is craft. The lyric is one of the great feats of pop songwriting: a first-person account of recognition so precise that millions of listeners have felt it was written about them. “Strumming my pain with his fingers, singing my life with his words” — the metaphor is exact, because that is what a great song does. It takes a private feeling and hands it back to you, shaped, named, and bearable. Flack’s performance honors that precision by refusing to oversell it. She sings the song the way the woman in the lyric hears it: quietly, intently, as if she cannot quite believe what is happening to her. The restraint is the emotion.
The other part of the answer is the song’s second life. By the mid-1990s, “Killing Me Softly with His Song” had been covered more than 450 times, but nothing prepared it for the Fugees. In 1996, the hip-hop group, with Lauryn Hill singing lead, released their version, and it became a phenomenon all over again: number one on the American airplay chart, number one in nineteen other countries, and winner of the Grammy for Best R&B Performance by a Duo or Group with Vocal. Hill’s version is brasher and warmer than Flack’s, but it works for the same reason Flack’s does — because the lyric is indestructible. Flack, gracious as ever, eventually performed the song on stage with the Fugees, closing the circle: the woman who had found the song on an airplane in 1972 now stood beside the young singers who had found it again, a quarter of a century later. The song has since been ranked number 273 on Rolling Stone’s list of the 500 Greatest Songs of All Time and number 82 on Billboard’s all-time Hot 100 songs.
There is a final pleasure in the story, and it belongs to Flack herself. She spent her twenties teaching children to read music, using pop songs to win their attention before she taught them notation. She spent her thirties singing in a club where the owner built her a room of her own. And she spent the rest of her life as proof that a whisper can travel further than a shout. When she accepted her second Record of the Year Grammy, she thanked, simply, “the world.” The world had a reason to thank her back. She had taken a song that began as a young woman’s scribbled notes on a napkin, and a recording that had passed unnoticed, and turned it into a record that taught generations of listeners what it feels like to be truly heard.
Flack died on February 24, 2025, at the age of eighty-eight, exactly fifty-two years to the day after “Killing Me Softly with His Song” first reached number one. The timing feels like something the song itself would have arranged. A song about a stranger singing your life back to you, recorded by a woman who spent her life listening carefully, kept its appointment with history to the very end. It still does its quiet work, every time it plays: it finds a listener, sits down beside them, and tells them, in a voice barely above a murmur, that they are not alone in what they feel.
Watch the video below and listen the way Flack listened that day on the airplane — closely, and all the way through.