During the 60's she began to shape her career as a singer by performing in clubs on weekends in the area. At first she accompanied other singers, while she would sing on her own during intermissions, then as a performer on her own. In one of those clubs, she was heard by jazz pianist Les McCann, who arranged an audition for her with Atlantic Records. She recorded her first album, "First Take" in late 1968 and was released the next year. At first, not many heard the album, but one person who did was Clint Eastwood.
The actor was in the process of making plans for his directorial debut on a film called, "Play Misty For Me" and was taken by one of the songs off of Flack's first album. "The First Time Ever I Saw Your Face" was written by folk singer Ewan MacColl back in 1957 and had been covered dozens of times. Flack had taken the song and slowed it down considerably for her recording, and Eastwood thought it would be a perfect fit in his new movie.
During 1971, she had begun to make some headway on the charts, mostly on the strength of two duets with Donny Hathaway, but when the movie and the song became hits, it propelled her to stardom. The song was nominated for a Grammy and was the first of four top five hits for Roberta during the 70's.