50 Years Since Roberta Flack Turned the Don McLean-Inspired “Killing Me Softly with His Song” Into a Hit

It all started with Don McLean.

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In November of 1971, 19-year-old singer Lori Lieberman was coaxed by a friend into seeing McLean perform at the Troubadour in Los Angeles and found herself utterly moved by the “American Pie” singer’s performance.

“Empty Chairs”

Touched specifically by McLean’s performance of his American Pie track, “Empty Chairs,” Lieberman said that listening to him was like hearing some of her own diary entries read aloud. Inspired by McLean, she began scribbling down some poetic verses on a napkin at the venue.

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“When he sang ‘Empty Chairs,’ I honestly felt that he was singing straight to me,” said Lieberman. “I felt like he was up there reading my diary, and singing about me and my life. I remember feeling embarrassed and exposed, as though people would somehow notice. The song talked about love that got lost and coming home to an empty house, and that really resonated with me in a painfully honest way.”

Lieberman continued, “When he left the stage and the audience filtered out, I stayed in my chair, and wrote a poem about my experience on a napkin.”

Soon after, Lieberman presented her lyrics for “Killing Me Softly With His Song” to songwriter Norman Gimbel, who collaborated with the young singer on the song, which was composed by Charles Fox. When Leiberman was denied songwriting credit on the track, she released her own version in 1972, which didn’t chart.

A year later, Roberta Flack came across the track.

Roberta Flack: 1973

“I was on a plane and read through a list of music channel song listings,” recalled Flack in a 2020 interview. “The title of the song [‘Killing Me Softly with His Song’] jumped out at me. I took out a notepad and listened to that song 10 times to get the melody and lyrics. When I landed, I called Quincy Jones, who helped me get the music charts.”

Flack went ahead and rehearsed the song with her band at Bob Marley’s studio in Kingston, Jamaica but didn’t record it yet.

Performing one night at the Greek Theatre in Los Angeles, where she was opening for Marvin Gaye, Flack was urged to come back on for an encore and perform “Killing Me Softly.”

“Marvin told me to sing another song,” said Flack. “I performed ‘Killing Me Softly,’ and the audience lost their minds. Marvin walked over to me, put his arm around me, and said, ‘Baby, don’t ever do that again live until you record it.’”

Once recorded, Flack’s version of “Killing Me Softly With His Song” went straight to No. 1 and won two Grammys for Record of the Year and Best Female Pop Vocal Performance in 1974.

The Fugees: 1996

More than two decades after the release of Flack’s “Killing Me Softly,” the song shot back up the charts after the release of The Fugees cover.

Sung by the Fugees’ Lauryn Hill, the song reached No. 1 in 10 countries, including the U.S., and picked up a Grammy for Best R&B Performance by a Duo or Group with Vocal in 1997.

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Flack has also joined the Fugees on several occasions to perform the song, including their performance at the 1996 MTV Movie Awards (see below).

Lori Lieberman Covers McLean

In 1995, Lieberman rerecorded “Killing Me Softly” for her album, Thousand Dreams, and has also covered “Empty Chairs” several times, including her recent version on her 2019 album The Girl and The Cat.

“I recorded ‘Empty Chairs, and when I perform it, I link it to ‘Killing me Softly,” shared Lieberman. “On my latest version, it begins with a long piano intro and is probably the most candid and honest version of mine to date.”

Read our 2022 interview with Roberta Flack HERE.

Photo by Jeri Jones / Reybee, Inc.