"Killing Me Softly with His Song" is a 1971 song composed by Charles Fox and Norman Gimbel. It was inspired by Lori Lieberman's response to having seen a performance by Don McLean. It has been covered by numerous artists, most notably by Roberta Flack, whose version topped the U.S. pop singles charts, and won a Grammy Award.

After singer/songwriter Lori Lieberman saw Don McLean singing his composition "Empty Chairs" in concert, she wrote a poem titled "Killing Me Softly with His Blues". It became the basis for the song written by Norman Gimbel and Charles Fox.

Lori Lieberman was the first to record Fox and Gimbel's song, in 1971. It became a bigger hit when covered by Roberta Flack in 1973. Her version won three Grammy Awards: Song of the Year, Record of the Year and Best Pop Vocal Performance by a Female Performer and it was number one on the Billboard Hot 100 for 4 weeks. It was replaced by "Love Train" by The O'Jays, then returned to the top of the U.S. charts for another week. In 1999 Flack's version was inducted into the Grammy Hall of Fame.

Hip hop group The Fugees covered the song in 1996 on their album The Score, with Lauryn Hill singing the lead vocals. Their version, titled "Killing Me Softly," became a hit, reaching number two on the U.S. airplay chart, and had similar success in the UK, reaching number one, becoming 1996's best selling single in the country. The version sampled the 1990 song "Bonita Applebum" by A Tribe Called Questfrom their debut album People's Instinctive Travels and the Paths of Rhythm. ATCQ themselves had sampled the riff from the song "Memory Band" found on the self-titled album of a little-known 1960s psychedelic soul Chicago band called Rotary Connection. The Fugees single was so successful that the track was 'deleted' and thus no longer supplied to retailers whilst the track was still in the Top 20 so that attention could be drawn to the next single 'Ready or Not'. Propelled by the success of the Fugees track, the version by Flack was remixed in 1996 and topped the Hot Dance Club Play chart. In 2008, it was ranked number 25 on VH1's 100 Greatest Songs of Hip Hop and #44 on its list of the "100 Greatest Songs of the 90s".

The Fugees version was released on 2 CD singles in the UK.

Other major artists to cover the song include Blossom Dearie, Al B. Sure!, Carole King, Herb Alpert, Engelbert Humperdinck, Tori Amos, Alison Moyet, Eva Cassidy, Perry Como, Harry Connick, Jr., The Jackson 5, Mina, Anne Murray, Sérgio Mendes & Brasil '77, Luther Vandross, Susan Boyle, Toni Braxton, Alicia Keys, Jaco Pastorius, The Plain White T's, The Youngblood Brass Band, Shirley Bassey, John Holt, Frank Sinatra, Vicki Lawrence, Usha Uthup, Gene Pitney and Allison Iraheta. Versions performed by male artists reverse the gender pronouns (with the exception of Luther Vandross).

In 1975, an instrumental version of "Killing Me Softly" served as the main musical theme of the film The Drowning Pool, starring Paul Newman. Charles Fox received credit as composer and conductor.

R&B artist Al B. Sure was the next to cover the song in 1988 on his debut album In Effect Mode...and experienced some success with it. He was voted the top new Male R&B solo artist in 1989.

A live instrumental version was recorded by Kermit Ruffins and the Barbecue Swingers in 1998.

In 1999, Susan Boyle, an amateur singer that quickly rose to fame on the internet and news media after her appearance on Britain's Got Talentin 2009, used "all her savings" to pay for a professionally cut demo tape, which she later sent to record companies, radio talent competitions, local and national TV and which has now been released on the Internet. It consisted of "Cry Me a River" and her version of "Killing Me Softly with His Song". Boyle gave away a few copies to her close friends.

The song was prominently featured in the 2002 film About a Boyin which the boy of the title, Marcus, is ridiculed by classmates for singing the song, a favourite of his mother's, at his school talent show because of its feminine associations and its romantic, emotional lyrics.

In 2006 the song became a popular football chant with Irish football club Shelbourne F.C. with the lyrics changed to "Dillon Me Softly with His Song" regarding former defender Sean Dillon. The chant has since followed Dillon to his new club Dundee United F.C..

Flack's version ranked #360 on Rolling Stone's list of The 500 Greatest Songs of All Time.

Flack's version also ranked at #82 on Billboard's Greatest Songs of all time.

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