Killing Me Softly: From Folk Whisper to Soul Classic to Hip-Hop Anthem

A song about a song that became one of the most covered compositions in modern music history. ‘Killing Me Softly with His Song’ started as a quiet folk recording inspired by a Don McLean concert, transformed into Roberta Flack’s intimate soul masterpiece, and was reborn 23 years later as the Fugees’ hip-hop soul phenomenon. This is the story of how three different artists—Lori Lieberman, Roberta Flack, and Lauryn Hill—each found something deeply personal in the same melody, creating three distinct classics that speak to three different generations.

It started with a mysterious concert, became one of the biggest soul hits of the 1970s, and was reborn as a hip-hop phenomenon in the 1990s. ‘Killing Me Softly with His Song’ has one of the most fascinating journeys in popular music—from Lori Lieberman’s delicate folk original through Roberta Flack’s Grammy-sweeping masterpiece to the Fugees’ generation-defining cover.

But did the song really start with a Don McLean concert? Why did Roberta Flack’s version eclipse the original so completely? And how did Lauryn Hill and the Fugees bring it to a whole new audience without betraying its soul?

This week on Uncovering the Cover, we explore a song about being moved by music—told through three artists, three decades, and three completely different approaches to the same haunting melody.

Featured: Lori Lieberman, Roberta Flack, The Fugees (Lauryn Hill, Wyclef Jean, Pras Michel), Charles Fox, Norman Gimbel