Roberta Flack’s Top Songs on Billboard Hot 100

Roberta Flack, the chart-topping, Grammy-winning singer-songwriter whose string of hits bridged sophisticated pop and vintage soul, died Monday (Feb. 24) at age 88. A product of piano-based classical training and the gospel stylings of the AME Church, Flack signed with Atlantic Records in 1968 after years as an educator and club performer around Washington, D.C.

In January 1970, Flack’s debut album, First Take, arrived on Billboard’s charts, including a No. 195 start on the Billboard 200. Among its eight tracks was a cover of a popular folk song, “The First Time Ever I Saw Your Face,” which emerged as a mainstream hit after Clint Eastwood borrowed it for his film directorial debut, Play Misty for Me, in late 1971. The track became Flack’s fourth career hit on the Billboard Hot 100 in March 1972, and by mid-April, became the singer’s first No. 1. Six weeks at the summit fueled “Face” to the year-end No. 1 Hot 100 honor, and it won Grammy Awards for record and song of the year in 1973. First Take, too, enjoyed spoils, pushing to No. 1 on the Billboard 200 for a five-week reign.

The following year repeated many of the same triumphs, with another No. 1 Hot 100 single, “Killing Me Softly With His Song,” and the record of the year Grammy Award. Flack nearly landed both victories for a third consecutive year, as her third and final Hot 100 leader, 1974’s “Feel Like Makin’ Love,” was also nominated for record of the year.

In all, Flack achieved 18 Hot 100 hits in her career, including six duets with her most frequent collaborator, Donny Hathaway, with classics “The Closer I Get to You” (No. 2) and “Where Is The Love” (No. 5) finding the strongest success. Her last appearance came in 1991, with the Maxi Priest collaboration “Set the Night to Music,” which peaked at No. 6.

Her material touched a new generation, too, through the Fugees’ rendition of “Killing Me Softly” from their seminal album, The Score. The hip-hop trio’s version soared to No. 2 on the Radio Songs chart from chart-topping results across multiple formats, including Pop Airplay and R&B/Hip-Hop Airplay, and won a Grammy Award for best R&B vocal performance by a duo/group.

To review the legend’s impact across popular music, here’s the official recap of Roberta Flack’s biggest hits on the Billboard Hot 100.

Roberta Flack’s Biggest Billboard Hot 100 Hits ranking is based on weekly performance on the Hot 100 from its Aug. 4, 1958, start through Feb. 22, 2025. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at lower spots earning the least. Due to changes in chart methodology over the years, eras are weighted differently to account for chart turnover rates during various periods.