RS: The Top 500 Songs in Modern Music History…Song #227: Killing Me Softly (With His Song) by Lori Lieberman/Roberta Flack/The Fugees.

This list of songs is inspired by a list published by radio station, KEXP, from Seattle in 2010, as well as, the latest poll taken in 2021 by Rolling Stone Magazine. For the most part, I will faithfully countdown from their lists, from Song #500 to Song #1. So, when you see the song title listed as something like: “KEXP: Song #XXX”….it means that I am working off of the official KEXP list. “RS: Song XXX” means the song is coming from the Rolling Stone list. If I post the song title as being: “KTOM: Song #xxx”….it means I have gone rogue and am inserting a song choice from my own personal list of tunes I really like. In either case, you are going to get to hear a great song and learn the story behind it. Finally, I am not a music critic nor a musician. I am a music fan and an armchair storyteller. Enough said! Let’s get on to today’s song.

RS: The Top 500 Songs in Modern Music History.

Song #227: Killing Me Softly by Lori Lieberman/Roberta Flack/The Fugees.

“Killing Me Softly (With His Song)” is somewhat like the “Star Wars” movie franchise, in that it has a interesting origin story, as well as a couple of sequels of note that help to extend our understanding and appreciation of the song. “Killing Me Softly (With His Song)” has won the Grammy Award TWICE for being “Song of the Year” in two different decades by two different artists. It has, also, been inducted into the Rock n’ Roll Hall of Fame TWICE in the “Song Category” for its’ significant contributions to the culture of society. And yet, the origins of how this song came to be and what happened to the original singer almost dwarf the success that came to be later on. Here is the story of “Killing Me Softly (With His Song).

One of the most famous songs of all-time is “American Pie” by Don McLean. Although McLean had other songs of note, it was his song, “American Pie”, about the deaths of Buddy Holly, Richie Valens and The BIg Bopper…..”the Day the Music Died”…that propelled him to everlasting fame. However, McLean wrote other songs that were as descriptive and personal as “American Pie”. One of those songs was called, “Empty Chairs”. It was while singing this song in a club one night that McLean, completely oblivious to this fact, set in motion a chain of events that resulted in the creation of “Killing Me Softly (With His Song). In the audience that evening was a 19-year old singer named Lori Lieberman. Lieberman had just entered into a recording contract with two older men named Norman Gimbel and Charles Fox. With her mind filled with the desire to write songs, the young, impressionable Lieberman sat at a table and listened to Don McLean croon out his words to “Empty Chairs”. There was something about how he sang, as much as what he sang, that struck a chord deep within Lieberman’s heart and mind. She began scribbling her thoughts/reactions down on a napkin. Among the words she wrote down were,

“I felt all flushed with fever,

Embarassed by the crowd.

I felt that he’d found my letters

And read each one out loud.

I prayed that he would finish

But he just kept right on.”

To McLean, it was just another concert. To Lieberman, it was a life-altering event.

The next day, Lieberman showed her notes to Gimbel and Fox and, a few days later, the basic outline of the song we have come to know as, “Killing Me Softly (With His Song) fell into place. However, the Lieberman side of this story is far from over. Like many young, idealistic young female singers, Lieberman soon fell under the sexual spell of a much older and more controlling man in the form of Gimbel. Gimbel ended up controlling Lieberman’s singing career, limiting what songs she was allowed to sing, demanding large percentages of whatever profit she made on the sale of her songs and, as well, restricting her access to other people; especially, other men. During their time ” as a couple”, the story about Lieberman hearing Don McLean sing, was used as a marketing tool to help sell, “Killing Me Softly (With His Song)”. However, after several years, Gimbel “grew tired” of this relationship and severed his ties with Lieberman. In doing so, he began to alter the origin story of the song; eliminating/reducing Lieberman’s role in its’ creation. It was only after litigation brought on by Lieberman, that she was given equal songwriting credit under the law, as well as, access to royalties that she had been denied by Gimbel. The Lori Lieberman version of the song was relased but never charted very well. But, it did receive enough attention to catch the ear of a young, up-and-coming Soul singer named Roberta Flack who, in her turn, saved the song and elevated it into the classic that we have all come to know and love.

Flack’s role in this story started when she was travelling on tour with singer, Marvin Gaye. As they flew to their next concert destination aboard an airplane, Flack passed the time by listening to the in-flight entertainment music channel. She decided to listen to a channel devoted to “New Releases”. It was while listening to this channel that Flack heard Lieberman’s version of “Killing Me Softly (With His Song)”. While she didn’t really care for the tempo and structure of the music, Flack fell in love with the lyrics and felt that she could bring something new and fresh to the song. Once she landed, she contacted her manager who, in turn, contacted Gimbel and Fox who were, at the time, the legally-listed songwriters of the song, and asked for permission to record it their way. For a fee, permission was granted. Flack changed the musical structure of the song and began playing around with it during rehearsals. Marvin Gaye heard her sing “Killing Me Softly (With His Song) and encouraged Flack to try it out during the encore part of the show. Reluctantly, she did. The audience loved the song and gave her a thunderous ovation. Encouraged by that reaction as well as, the advice of Gaye who told her to record and release the song immediately, Roberta Flack found herself with the biggest hit of her career.

Fast forward almost decades later. A jazzy, soul-influenced Hip Hop group called, The Fugees was looking for material to add to the release of their debut album. While the group held many talented players, it was lead singer, Lauryn Hill, who became the face of the group and who was the star that emerged a few years later. So, they were looking for a song that could serve as a vehicle for Hill. An updated re-boot of Roberta Flack’s version of “Killing Me Softly (With His Song) seemed like the right choice. In The Fugee’s version, they sampled freely from other songs by other singers and groups such as, A Tribe Called Quest and ended up creating a completely new song that used Flack’s version as its foundation but complemented that with funky, Hip Hop-infused elements that modernized the song for newer times. In both the case of Roberta Flack and The Fugees, those cover versions of the Lieberman song, inspired by Don McLean, scored “Song of the Year” Grammy Awards and Hall of Fame inductions for each.

Below, I will play all three versions of the song; starting with the rightful songwriter, Lori Lieberman’s version. My personal favourite has always been Roberta Flack’s soulful song stylings. Which version, if any, do you like the best? Let me know in the comments below.

The link to the video for the song, “Killing Me Softly (With His Song)” by Lori Lieberman, can be found here.

The link to the official website for Lori Lieberman, can be found here.

The link to the video for the song, “Killing Me Softly (With His Song)” by Roberta Flack, can be found here.

The link to the official website for Roberta Flack can be found here.

The link to the video for the song, “Killing Me Softly (With His Song)” by The Fugees, can be found here.

The link to the official website for The Fugees, can be found here.

The link to the official website for Rolling Stone Magazine, can be found here.

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