just a little Rare songs become pop classics. But this one has become a classic twice. “Killing Me Softly with His Song” has one of the longest and strangest ballads in pop history. In the 1970s, it went to No. 1 as a soft rock ballad for R&B superstar Roberta Flack. In the 1990s, it became a hip-hop smash for the Fugees, showcasing Lauryn Hill’s vocals. Some fans prefer Flack’s soft, mellow version; others prefer the Fugees’ reggae-flavored remake. But both versions have become perennial classics that live on to this day. Either way, this song is still killing listeners softly.
Not only did “Killing Me Softly” make Rolling Stone's list of the 500 Greatest Songs of All Time, it also made the list twice. Roberta Flack's 1973 hit came in at number 273, while the Fugees' 1996 hit came in at number 359. It's the only song on the list to appear in two different versions.
In this week's episode of rolling stones On 500 Greatest Songs, hosts Rob Sheffield and Brittany Spanos discuss the long history of “Killing Me Softly,” and how these two different versions continue to grow in stature over the years. They’re joined by fellow Rolling Stone great David Browne, who explains how the ’70s pop song became a ’90s hip-hop hit, and why both versions remain universally beloved.
“Killing Me Softly” had a famous story, and no one had denied it for years. The inspiration was folk star Don McLean, the man who wrote “American Pie.” One night in Los Angeles, a 19-year-old songwriter named Lori Lieberman went to see him live at the Troubadour. When she heard him sing the deep-bassed “Empty Chairs,” something intense happened. To her, the song seemed to invade her soul—it felt like McLean was fingering the strings of her destiny, singing her life with his words. “I was moved by his performance,” she told the Troubadour. New York Daily News In 1973, “the way he developed his numbers, he was able to influence me.” She was so excited, she began writing the lyrics on her napkin during the show.
Lieberman recorded the original version on her 1972 debut album, though few people had heard it at the time. The writing credit went to veteran Hollywood songwriting team Norman Gimbel and Charles Fox. They were best known for television themes such as happy Days And Love snakeThis song was one of their best ever, along with Jim Croce’s hit “I Got a Name.” People loved the origin story of “Killing Me Softly”—it became part of the song’s legend. But things got weird decades later when Gimple and Foxx fell out with Lieberman and changed their story. They spent years denying she was ever involved, trying to erase her (and MacLean) from the story.
Flack heard “Killing Me Softly” on a plane, as in-flight music, and fell in love with it, just as Lieberman fell in love with McLean’s song. Flack recorded the song with a band full of jazz greats, including the legendary Ron Carter on guitar, and backing vocals from her longtime duet partner Donny Hathaway. It was part of her stellar 1970s career, including “Feel Like Making Love,” “The First Time Ever I Saw Your Face,” and her best collaboration with Hathaway, “Where Is The Love?” She had her own unique style: quiet, contemplative, simple, smooth. “Killing Me Softly” became her signature song.
The Fugees came to the song at the moment they were ready to break out of the hip-hop world with their 1996 classic, The resultThe entire album was filled with potential hits: “Ready Or Not,” “Fu-Gee-La,” “Cowboys,” the Nashville-tinged “Family Business,” and the strangely underrated “Killing Me Softly.” “Killing Me Softly” was like nothing else on the album, but it became a hit. It never made it onto the Billboard Pop charts because it wasn’t commercially available as a single, but it was all over the radio as a summer soundtrack everywhere.
The Fugees didn't change much about the song, except for two great touches: the “one time” in the chorus, and the sitar hook, which was taken from A Tribe Called Quest's “Bonita Applebaum.” “Killing Me Softly” introduced the world to Hill's skills as a soul singer. In some ways, it sounded more like a Hill solo than a Fugees song, with little room on the mic for either of the other two Fugees, Wyclef Jean or Pras Michael. It was essentially a reworking of the style of their 1998 classic. The Miseducation of Lauren HillWith the R&B power you've heard on classics like “Ex-Factor,” however, the Fugees' version never left the radio, just like Roberta Flack's version – two different sides of the same timeless song.
In 2004, Rolling Stone magazine released its list of the 500 greatest songs of all time. Compiled through a massive vote by artists, music figures, and critics, the list has been a source of conversation, inspiration, and controversy for two decades. It is one of the most popular, influential, and controversial articles the magazine has ever published.
So, we decided to make it bigger, better, and more modern. For 2021, we’ve completely overhauled our 500 Songs list, with a whole new cast of voters from across the music map. Rolling Stone’s 500 Songs takes a closer look at our entries. In partnership with iHeart, Rolling Stone’s 500 Songs finds Brittany and Robbie discussing a new song each week, delving into its history and impact with the help of a special guest—including RS colleagues, producers, and the artists themselves. It’s our celebration of the greatest songs ever made—and a breakdown of what makes them so great.
Check out the latest episode above, on iHeart, or wherever you get your podcasts, and look for new episodes every Wednesday.
