The passing of Roberta Flack is the end of an era, one marked by her pioneering experimentation with the boundaries of genre in popular song. The four-time GRAMMY winner and Recording Academy Lifetime Achievement Award recipient died on Feb. 24 at age 88. 

"The world has lost a musical great with the passing of the timeless Roberta Flack. A visionary artist and humanitarian, she created music that transcended genres, cementing her legacy as one of music’s most influential voices," said Recording Academy CEO Harvey Mason jr. "We honor her creative spirit, boundless talent, and lasting impact on music and beyond."

Flack began her musical life in two different universes: playing classical piano and singing opera; and performing in churches in her Arlington, Virginia hometown (her mother, Irene, was a church organist). A teenage Roberta was talented enough that she got a full scholarship to Howard University at 15 years old.

As a young adult, Flack was warned against an opera career by a vocal coach — one who, as a 1975 Time article put it, "gently suggested a pop singing career." She took the suggestion seriously, and began performing in nightclubs. Discovered by jazz legend Les McCann, she ended up signed to Atlantic Records.

That’s where Flack’s story really begins. Her debut album, 1969’s First Take, introduced the world to a startling talent who had melded all of her musical lives and influences into a seamless whole. Was the result folk? Jazz? Soul? No one knew, but few seemed to care. 

Her repertoire, even on that first album, was vast, spanning from musical theater numbers to anti-war protest songs to spirituals to an achingly beautiful take on Leonard Cohen’s "Hey, That’s No Way to Say Goodbye."

"Goodbye" is emblematic of Flack’s genre-spanning reach: it has nylon-string acoustic guitar similar to Cohen’s folk-styled original, upright bass by jazz legend Ron Carter, piano from Flack herself that wouldn’t be out of place on a Carole King record, and a string arrangement that hearkened back to the singer’s first love of classical music — and that’s all just in the first minute. 

First Take’s most famous track, "The First Time Ever I Saw Your Face," wasn’t a hit at first. It took the song being placed in a Clint Eastwood movie — two years after the album’s original release — to get the momentum really going. "Face" won Record Of The Year at the 15th GRAMMY Awards in 1973, though Flack had received a nomination the year prior for her duet with her friend and frequent collaborator Donny Hathaway for "You’ve Got a Friend." 

That Record Of The Year win was just the beginning; Flack took home a golden gramophone in the same Category again the following year — the first person ever to do so, and the only artist until U2 duplicated the feat in 2001-02. That winning song (which also won Best Pop Vocal Performance, Female) came to be Flack's best-known hit.

"Killing Me Softly With His Song" (a song, as the story goes, inspired by Don McLean of "American Pie" fame) had been released by Lori Lieberman in 1972 to almost no response. But in Flack’s hands, it became a masterpiece. It was so iconic, in fact, that it became a career-making hit again two decades later when the Fugees reimagined Flack’s version of the song for the hip-hop generation. Flack's version was inducted into the GRAMMY Hall Of Fame in 1999, one of two songs honored in such a manner.

After the massive success of "Killing Me Softly" and her album of the same name, Flack took a 15-month break. She was overwhelmed by her work schedule; by the endless people, as she put it at the time, "backing you into a corner and telling you to sing soul" because of her race and gender; and by a need to try new things. When Flack came back with 1975’s Feel Like Makin’ Love, she was fully in control, without longtime producer Joel Dorn and with a very lucrative new five-year record contract. 

That control expanded beyond the business world. While she was from the beginning a top-notch finder and interpreter of songs, as her career went on she began to write more frequently as well. She was inducted into the Women Songwriters Hall of Fame as part of their inaugural class. 

While Roberta Flack’s style doesn’t lend itself easily to imitation, that doesn’t mean she wasn’t incredibly influential. 

"Within Black communities and among artists of color, Flack's music has always remained a central guiding force," Ann Powers wrote in 2020. This can be most clearly seen in the R&B style that became known as "quiet storm." 

"The songs framed within this label span across pop, R&B, soul, jazz and jazz fusion," PBS’ "American Masters" explained of quiet storm. With a description like that, it’s no surprise that the titular "master" is, of course, Roberta Flack. Her early work, like the aptly-titled 1971 project Quiet Fire, helped birth the style, which then took over the world in the early 1980s. 

Flack’s life, career path, and the company she kept were as varied as her music. She sang at Jackie Robinson’s funeral, lived in the same building as her friends John Lennon and Yoko Ono, toured with Miles Davis in the mid-1980s, was a huge supporter of Jesse Jackson’s Operation Breadbasket, composed and produced the Bustin’ Loose soundtrack, hosted a weekly radio show, made a Christmas album, joined with Madonna and Wynonna to save the rainforests, performed for Nelson Mandela, founded a music school…and that’s hardly scratching the surface. 

"I've always tried to express myself musically from a place of complete honesty in the hope that each person can find his or her own story when they listen in a way that helps them to feel their own truth," Flack once said. 

While her style can never be duplicated, what we can take away from Flack’s life and music is that powerful dedication to your own truth, whatever road (or genre) it may lead you down.