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Forever No. 1 is a Billboard series that pays special tribute to the recently deceased artists who achieved the highest honor our charts have to offer — a Billboard Hot 100 No. 1 single — by taking an extended look back at the chart-topping songs that made them part of this exclusive club. Here, we honor Roberta Flack, who died on Feb. 24 at age 88, by looking at the singer’s second of three No. 1 hits as a recording artist: the instant standard “Killing Me Softly With His Song.” (In case you missed it, here’s a look at her first No. 1, “The First Time Ever I Saw Your Face.”)

Roberta Flack could have brought a book or a magazine to read on an American Airlines flight from L.A. back home to New York in 1972. She could have watched the in-flight movie or even taken a nap. Let’s all be grateful that she instead chose to listen to the in-flight audio program, which included a pretty pop/folk ballad recorded by a then-20-year-old singer named Lori Lieberman.

Flack scanned the list of audio selections and learned that the composition, “Killing Me Softly With His Song,” was written by Norman Gimbel and Charles Fox. Gimbel was then best-known for writing English-language lyrics to such global hits as “The Girl From Ipanema” and “I Will Wait for You”; Fox for creating the sunshine pop musical backgrounds on the hit ABC show Love, American Style.

“The title, of course, smacked me in the face,” Flack later said. “I immediately pulled out some scratch paper, made musical staves [and then] play[ed] the song at least eight to 10 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.”

By most accounts, the song was inspired by Lieberman seeing Don McLean perform at the Troubadour club in Los Angeles in November 1971. McLean’s “American Pie” entered the Billboard Hot 100 that month (on its way to No. 1 in January 1972), but Lieberman was more taken by another song in the set, the haunting ballad “Empty Chairs.” The singer jotted some notes and impressions on a napkin. She later described the experience, and how deeply it affected her, to Gimbel, with whom she was working at the time. (Gimbel and Fox had signed her to a five-year production, recording and publishing deal.)

Lieberman’s description reminded Gimbel of a phrase that was already in his idea notebook: “to kill us softly with some blues.” The phrase had appeared five years earlier in a novel by Argentinian writer Julio Cortázar and Gimbel thought it had possibilities. Gimbel drew from Lieberman’s account, crafted the lyrics, and passed them on to Fox, who set them to faintly melancholy music.

Lieberman did not receive a co-writing credit on the song. There is even a dispute over whether, and to what degree, the song was inspired by McLean’s performance. When Dan MacIntosh of Songfacts asked Fox in 2010 about the McLean origin story, Fox said: “I think it’s called an urban legend. It really didn’t happen that way.”

Lieberman had a falling out with Gimbel (who died in 2018) and Fox (who is still living at 84). This backstage drama is intriguing, but mostly irrelevant to the story of Flack’s recording, which quickly became one of the biggest and best (and most celebrated) singles of its era.

Jones, who died less than four months ago, played a key role in this story a second time. In September 1972, Flack was opening for Jones at the Greek Theater in Los Angeles. Flack was red-hot at the time, having landed million-sellers that year with the classic ballad “The First Time Ever I Saw Your Face” and the ebullient “Where Is the Love,” a silky duet with Donny Hathaway.

When the audience at the Greek kept cheering, Jones advised her to go back out and sing one more song. “Well, I have this new song I’ve been working on,” Flack replied. “After I finished [‘Killing Me Softly’], the audience would not stop screaming. And Quincy said, ‘Ro, don’t sing that daggone song no more until you record it.’”

As usual, Jones’ instincts were correct. Flack recorded the song on Nov. 17, 1972 at Atlantic Studios in New York. Flack arranged the track, Joel Dorn produced it and Gene Paul engineered. Flack also played piano on the track, while Hathaway contributed harmony vocals. The other musicians were Eric Gale (guitars), Ron Carter (bass), Grady Tate (drums); and Ralph MacDonald (congas, percussion, tambourine).

Flack completely transformed the song. Lieberman’s version of the song, produced by Gimbel and Fox and arranged and conducted by Fox, is pretty, but rather bland. Her version plays like a very good demo, which is essentially what it was.

Flack boldly restructured the song. Her recording has a cold open on the chorus “Strummin’ my pain…” Lieberman’s version opens with a long, moody piano solo (which sounds like it could have been featured in Love Story, one of the biggest movies of the era). Then she sings the first verse, only hitting the “Strummin’ my pain” chorus at the 0:51 mark.

Flack also transformed the song from a pop/folk tune to one that drew from a wide range of American music forms – pop, soul and jazz. A 25-second section, which doesn’t appear at all in the Lieberman version, borrows from the scatting tradition. Lieberman’s version ends with a 40-second instrumental outro. In Flack’s version, she is singing until the final note. And Flack sings the song with more passion, bringing out all the drama of the key line, “I felt he found my letters/ and Read Each One Out Loud!”

Flack’s transformation of this song was as complete as Aretha Franklin’s reinvention of Otis Redding’s “Respect” or Ike & Tina Turner’s re-imagining of Creedence Clearwater Revival’s “Proud Mary.” All three remakes show the power of interpretation – just as Lieberman’s largely unsung involvement in the song’s creation shows the importance of inspiration.

“Killing Me Softly” runs 4:46, longer than any other No. 1 hit on the Hot 100 in 1973. But it doesn’t seem long or padded as it seamlessly moves from section to section.

Fox has suggested that Flack’s version was more successful than Lieberman’s because Flack’s “version was faster and she gave it a strong backbeat that wasn’t in the original.”  According to Flack: “My classical background made it possible for me to try a number of things with [the song’s arrangement]. I changed parts of the chord structure and chose to end on a major chord. [The song] wasn’t written that way.”

Flack’s version was released as a single on Jan. 22, 1973, with a version of Bob Dylan’s “Just Like a Woman” (drawn from her 1970 album Chapter Two) on the B-side.

It was the top new entry on the Hot 100 (at No. 54) on the chart dated Jan. 27. It reached No. 1 on Feb. 24, displacing Elton John’s first Hot 100 No. 1, “Crocodile Rock.” “Killing Me Softly” reached the top spot in just five weeks, the fastest climb since Sly & the Family Stone’s “Family Affair” also reached No. 1 in its fifth week in December 1971. “Killing Me Softly” held tight in the top spot for four weeks before being bumped to No. 2 by The O’Jays’ exuberant “Love Train.”

But “Killing Me Softly” wasn’t done yet. It returned to the top spot for a fifth and final week before being dislodged for a second time by Vicki Lawrence’s “The Night the Lights Went Out in Georgia.” Flack’s five-week run at No. 1 was the longest by any single in 1973.

Flack was a perfectionist, which came into play here in at least two ways. Flack rehearsed the song with her band in the Tuff Gong Studios in Kingston, Jamaica, but she wasn’t satisfied with the background vocals on the various mixes. An executive at Flack’s label, Atlantic Records, assured her it would be a hit song no matter which mix was released. She refused to be rushed, recalling later that she “wanted to be satisfied with that record more than anything else.”

Also, Flack didn’t release an album with “Killing Me Softly” until Aug. 1, 1973, more than six months after the single’s release. That delay must have been agonizing for Atlantic executives. The album, with the shortened title Killing Me Softly, reached No. 3 on the Billboard 200 in September 1973. It would almost certainly have been a No. 1 album if it had been released while the single was being played every hour on the hour on every pop, soul and adult contemporary radio station in the land.

Flack followed “Killing Me Softly With His Song” with a slow and somber Janis Ian ballad, “Jesse.” It stalled at No. 30 on the Hot 100.

At the Grammy Awards on March 2, 1974, Flack became the first artist to win record of the year two years running, after taking home the award in 1973 for “The First Time Ever I Saw Your Face.” When Diana Ross announced her as the 1974 winner, a dazed Flack put her hand over her mouth. When she spoke, she simply said, “I’d like to thank the world.” (Since 1974, just two other artists have won back-to-back Grammys for record of the year: U2 triumphed in 2001-02 with “Beautiful Day” and “Walk On,” while Billie Eilish scored in 2020-21 with “Bad Guy” and “Everything I Wanted.”)

Flack won a second Grammy for “Killing Me Softly” – best pop vocal performance, female. (She probably should have won a third, best arrangement accompanying vocalists, but she wasn’t even nominated for that one.) The recording was inducted into the Grammy Hall of Fame in 1999.

Killing Me Softly was also nominated for album of the year (losing to Stevie Wonder’s Innervisions). It marked the first time in Grammy history that Black lead artists won album of the year and record of the year in the same year. Gimbel and Fox won song of the year for writing the song.

Flack re-recorded the song with Peabo Bryson on their 1980 double live album Live & More (its title borrowed from Donna Summer’s 1978 collection).

Many other artists have recorded the song over the years, including Johnny Mathis, on his 1973 album Killing Me Softly With Her Song; Al B. Sure!, on his 1988 album In Effect Mode; and Luther Vandross, on his hit 1994 collection Songs.

Fugees recorded an updated, but still faithful and deeply respectful version of “Killing Me Softly” (they shortened the title) on their second album, The Score, in 1996. Group member Pras made the suggestion to cover the song, which showcased Lauryn Hill on lead vocals.

The song reached No. 1 on both the Pop Airplay and R&B/Hip-Hop Airplay charts and No. 2 on Radio Songs. It likely would have been one of the year’s biggest Hot 100 hits were it not for rules at the time disqualifying songs not given an official single release. The track won a Grammy for best R&B vocal performance by a duo/group and an MTV Video Music Award for best R&B video. Flack and Fugees teamed to perform the song on the MTV Movie Awards on June 8, 1996.

Flack’s original track was remixed in 1996 by Jonathan Peters, with Flack adding some new vocal flourishes; this version topped the Hot Dance Club Play chart in September 1996.

Flack returned to the No. 1 spot on the Hot 100 for a third and final time in 1974 with the silky “Feel Like Makin’ Love.” But let’s save that story for the next Forever No. 1 installment.