Flack's music career took off in D.C., where she also continued to work as a teacher at the Rabaut and Brown junior high schools in the D.C. public school system. She began performing in the evenings at locations such as the Tivoli Theater and Mr. Henry’s in the District. At the Tivoli, she also worked as a backing pianist for opera singers, and her spark as a solo performer came with a rendition of “Jingle Bell Rock” performed at the restaurant, where Flack said it was her "cue that people would listen to [her] as a singer.”

Mr. Henry’s became one of her regular venues, and the club’s owner, Henry Yaffe, even turned the apartment above the club into the “Roberta Flack Room” for her performances – adding in church pews and a Mason & Hamlin piano to create a more intimate energy than the more raucous main stage. She started off playing Sunday brunch sets for $20 a week, initially with a folk-inspired repertoire. However, as her fame and success as a performer quickly grew, she began to consider pursuing it full-time. Of this time in her life, she said:

"It took courage to leave my classroom job because I was a Black person who had grown up in Arlington, Virginia, through the ‘50s and ‘60s; now I’m teaching school in the late ‘60s and I decide I want to sing. These days, there’s lots of things that you can go for, but in those days you had to have a lot of heart and a strong desire to do that.”

In 1969, she recorded her first album, First Take, with Atlantic Records. Aptly recorded in only 10 hours, the song’s discography was informed by pieces she had developed at Mr. Henry’s. Flack continued to return to the venue as her career took off, using it as a home base during her other performances in the District.

One of her first big hits was from that first album when in 1973 Clint Eastwood featured her song “The First Time I Ever Saw Your Face” (a folk ballad Flack had taught to her students in school glee clubs) in the film “Play Misty for Me.” Flack collaborated with many artists over the course of her career, including Donny Hathaway, Peabo Bryson, and for her album Oasis, Flack collaborated with longtime friend Maya Angelou on four songs, including “And So It Goes.”

Flack has continued to make music well into the 21^st century, and in 2020, was the recipient of the Grammy’s Lifetime Achievement Award.

Learn More

“Cover Me: The Stories Behind the Greatest Cover Songs of All Time” features a section discussing the history of Roberta Flack’s cover of “Killing Me Softly,” and the subsequent Fugees rendition.