What song is ‘Killing Me Softly With His Song’ about?

A heartbreaking song about a heartbreaking song is certainly a novel idea. However, what transfigures the track – whether it be Lori Lieberman, Roberta Flack or The Fugees’ version – beyond that power of art premise, is that it always carries an air of lived-in experience, a sense of awed sincerity. And it all stemmed from one fateful night in 1971, and a performance that will soon have you uttering: ‘God, I wish I had been there to see that’.

On a winter’s evening in ’71, the 20-year-old songwriter and aspiring performer Lori Lieberman was at a loose end. She had signed a collaborative contract with veteran songwriter and composing duo Norman Gimbel and Charles Fox, but she was yet to get her career off the ground. So, when her friend Michele Willens called her and asked whether she’d like to join in attending a concert at the Troubadour in Los Angeles, she was quick to accept despite knowing very little about the performer.

“I had heard about him from some friends but up to then all I knew about him really was what others had told me,” she said of the performer that night, Don McLean. So, like the inversion of the biblical Saul, she went into the concert blind and had her world illuminated. While the rest of the audience awaited ‘American Pie’ which was fresh in the charts and ready to climb to its current lofty height, Lieberman was just listening along to everything he had to offer. Suddenly, she felt sideswiped by his stunning performance of ‘Empty Chairs’. As he stirred her soul with his arresting performance, she began scribbling notes on a napkin.

After the concert, she raced to a phonebooth, called her songwriting partner Norman Gimbel and relayed her napkin’s musical eulogy to a performer putting their all into a piece of music. “I was moved by his performance, by the way he developed his numbers, he got right through to me,” she told the New York Daily News in 1973.

With the song now being honed beyond its humble napkin origins, Lieberman, Gimbel and Fox worked to channel McLean’s magic into their own masterpiece. High on inspiration, they raced to get the song out. Lieberman’s version was released a few months after she saw McLean’s concert, and sadly her efforts failed to chart. However, this first draft had more than enough promise to titillate a few ears within the industry, and soon a quirk of fate would tease Roberta Flack into trying her hand at it.

Lieberman’s version had worked its way onto an aeroplane’s in-flight audio program. When Flack took her seat, she looked through the list of songs available to listen to. “The title, of course, smacked me in the face. I immediately pulled out some scratch paper, made musical staves [then] play[ed] the song at least eight to ten times jotting down the melody that I heard. When I landed, I immediately called Quincy [Jones] at his house and asked him how to meet Charles Fox. Two days later I had the music,” Flack told NME.

The depths of the inspiration were relayed to Flack who looked to replicate that sense of sincere humbling in her own version. Imagining the building beauty of McLean steadily mounting the emotion of ‘Empty Chairs’, Flack used her classical background to make the composition swell and soon the track was reaching such an impassioned crest that Flack had to play it live before it was even recorded. She couldn’t contain it. And audiences couldn’t contain their delight when they heard it either.

It took the wise head of old Quincy Jones to recognise that dishing out a hit before your name is attached to it might not be such a great idea. As she comically recalled: “After I finished, the audience would not stop screaming. And Quincy said, ‘Ro, don’t sing that daggone song no more until you record it.'” Nevertheless, the audience’s reaction said it all; if McLean’s soul-stirring ways had toppled the first domino then this was the satisfying full circle.

McLean would later learn of the connection in 1973 and commented: “I’m absolutely amazed. I’ve heard both Lori’s and Roberta’s version and I must say I’m very humbled about the whole thing. You can’t help but feel that way about a song written and performed as well as this one is.”

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