Roberta Flack’s ‘Ballad’ for the Stonewall generation

R&B icon Roberta Flack has scored many hits over her more than five-decade long career. From “The First Time Ever I Saw Your Face,” “Where Is the Love,” and “Killing Me Softly” to her interpretations of songs by Leonard Cohen and The Beatles, Flack’s musical arrangements tend to strip songs bare so her voice can fill them with new meaning. In her 1969 release, “Ballad of the Sad Young Men,” she sings directly to gay men.

The origin of the song begins with the 1959 Broadway musical The Nervous Set. Adapted from an unpublished novel by Jay Landesman, the musical (also written by Landesman) follows a wealthy publisher navigating a dysfunctional marriage set in the Beat Generation-era of New York City. 

The musical was far from a success, closing its Broadway run after around 23 performances. But several of the songs from the production, including “Ballad of the Sad Young Men,” written by lyricist Fran Landesman (Jay’s wife) and composer Tommy Wolf found a second life.

In its original form, “Ballad of the Sad Young Men” had a typical campy musical theater arrangement as it highlighted the nihilistic and self-destructive habits of the post-World War II and pre-Vietnam America young generation in a satirical fashion. Dame Shirley Bassey’s rendition is as close to a musical theater style that’s out there. However, when Flack got ahold of the song, recording it for her album “First Take,” she breathed soul, sadness, and new sentiment into its lyrics as an ode to the Stonewall Generation and the fight for LGBTQ+ rights

“All the sad young men, sitting in the bars, knowing neon lights, and missing all the stars” the lyrics go. In another part, the sad young men are “drifting through the town, drinking up the night, trying not to drown.”

It’s a poignant scene that could touch anyone who has ever felt adrift by life. But Flack’s interpretation, timing and timbre spoke to the feelings of loneliness many queer men felt pre-Stonewall, and the songs meaning later reverberated into the ostracism gay men felt again during the HIV/AIDS epidemic. 

What’s more is Flack made sure to publicly and emphatically express that the song was dedicated to her gay audience. 

“A strictly heterosexual reading of [‘Ballad of the Sad Young Men’] would be very anti-feminist,” she told music journalist Chris Albertson in a 1978 interview for Routes magazine. “That’s not where I was coming from at all—it was all gay, straight down the line, I mean that’s the way I did it.” 

During live performances, when Flack’s star power shined brightest, “Ballad of the Sad Young Men” became a stable. In the book “Listen Again: A Momentary History of Pop Music,” Eric Weisbard writes that the singer openly discussed the meaning of the song her live shows as early as 1971.

“Lest its impressionistic lyrics be misunderstood,” he writes. “There is no way to fully emphasize the political risks Roberta Flack may have faced as an R&B singer in the late ’60s, ’70s and ’80s performing and discussing songs advocating human rights for gay men and women.”

For this reason, Flack has remained a gay icon among those in-the-know. 

Flack famously was the first musical artist to win the Grammy Award for Record of the Year for two consecutive years, for “The First Time Ever I Saw Your Face” in 1973 and “Killing Me Softly with His Song” the following year.

Before Flack was THE Roberta Flack, she was a schoolteacher moonlighting as a musician in Washington, D.C. She had regular gigs at a restaurant called Tivoli, and it was there where said she found her queer following.

“It was basically an underground place frequented by a lot of gay people, and these were, of course, very sophisticated people, lovers of opera and fine things,” she told Albertson. “It just opened up a whole new world for me, because they appreciated me so much.”

Speaking about her career later in an interview with The Guardian in 2020, she shared: “I didn’t try to be a soul singer, a jazz singer, a blues singer – no category.” Flack continued, “My music is my expression of what I feel and believe in a moment.”

That same year, she was honored with a Lifetime Achievement award at age 82 as part of the 2020 Grammy Awards.

“I am humbled and honored to be recognized in the company of such esteemed and diverse talents,” she said of the recognition.

Two years later, Flack revealed that she has been unable to sing due to an ALS diagnosis. But today, her voice and sense of activism is still as strong as ever in her catalog of iconic songs. 

Listen to the live stage version of “Ballad of the Sad Young Men,” below.