In the late 1960s, Roberta Flack’s rise from a D.C. schoolteacher to a music icon began on a stage at Mr. Henry’s on Pennsylvania Avenue. On Monday, the club mourned the loss of Flack at the age of 88.

“She will be incredibly missed,” Mr. Henry’s General Manager Cathy Nagy said.

Nagy said Flack, who grew up in Arlington, first started performing at the club on occasion while she taught junior high school in D.C. The singer and pianist would approach the club’s then-owner, Henry Yaffe, about her desire to follow her musical dreams, and Nagy said Yaffe wanted to help her do that.

“He essentially built out that second floor room, which is our music room now to this day, with kind of church-style pew seating to accommodate her crowds, and it took off from there,” Nagy said.

Nagy said the rest was history, as Flack would soon be discovered at the club and begin her rise to fame.

Even after becoming a household name in music, Flack, according to Nagy, never forgot the venue that helped launch her career. Nagy said it wasn’t out of the ordinary for Flack to stop by while in town to listen to the music and order the club’s crab cakes.

Nagy said Flack’s most recent visit was her return to D.C. for a ceremony in 2022, during which an iron call box close to Mr. Henry’s was dedicated to the entertainer.

“I have a picture that she took with a lot of our staff and our team here, and we were selling Henry’s blankets, and she asked, ‘Could I have one of those to drape over myself for the picture?’ which was so incredibly sweet,” Nagy said.

Over the decades, Nagy said many would come into Mr. Henry’s and talk about Flack and her story. Among them, she recalls one of Flack’s last junior high school students.

“He said she announced at the end of the year that she wasn’t coming back to teach, that she would be concentrating on her music career, and it was starting here,” Nagy said.

The significance of performing on the second floor of Mr. Henry’s is not lost on the artists who play there today, with some saying they can’t believe they are “on the stage that Roberta Flack was discovered on,” she said.

“She’s left an indelible mark on Henry’s and is woven into the fabric, for sure,” Nagy said.