Inspired by Martha’s Vineyard’s most famous musical family, the new documentary Born Into the Gig follows five performers who grew up in the orbit of their superstar parents and grandparents before seeking their own creative spotlights. Siblings Sally and Ben Taylor are profiled on the Vineyard, Kori Withers in Los Angeles and New York, Chris Stills from California to France and Skip Marley in a host of locations.

With so much traveling and so many subjects, the documentary itself took about three years to make, said producer Tamara Weiss of Chilmark. But the idea had been on her mind for much longer before she enlisted Oscar-nominated Island filmmakers Kate Davis and David Heilbroner to direct Born Into the Gig.

David Heilbroner is a former Manahattan prosecutor-turned author and director. — Jeanna Shepard

She just had to wait for her subjects to grow up.

A childhood friend of Carly Simon’s family in Riverdale, N.Y., Ms. Weiss also was a longtime employee of James Taylor. The couple’s daughter, Sally, was born in 1974 and Ben arrived three years later.

“Having been involved with the Simon-Taylor tribe, I had the opportunity to watch Sally and Ben grow up to music as a way of life,” Ms. Weiss told the Gazette this week, as Born Into the Gig wrapped up its run at the Martha’s Vineyard Film Society FILMusic Festival.

“I saw what it was like, and I thought it was quite brave of them to pursue that career choice,” Ms. Weiss said.

As the siblings found their own voices, she kept thinking about telling their story.

“It was aways percolating in my mind, mostly because I loved the music I heard . . . from Sally and Ben,” she said. Gradually, the concept evolved into an exploration of other next-generation performers as well.

Ms. Weiss met Chris Stills through another Vineyard connection, actress Amy Brenneman, who introduced the two by phone. “We just immediately hit it off,” Ms. Weiss said.

Like the Taylor siblings — and born the same year as Sally — Mr. Stills is the adult child of two superstars. His parents are folk-rock guitarist and singer-songwriter Stephen Stills and French singer-songwriter Veronique Sanson. After growing up as a tag-along, clambering around backstage while his parents toured and partied, Mr. Stills today is a working musician with children of his own, whom he is raising away from the entertainment scene.

Still a teenager during filming, Skip Marley is a third-generation entertainer whose voice resembles that of his maternal grandfather, reggae pioneer Bob Marley. When the documentary begins, he’s writing songs in his bedroom. By the end of the film, he’s performing at the Grammy Awards with Katy Perry.

The film also follows soul-inflected singer-songwriter Kori Withers as she records her first album in New York and hangs out with her parents in L.A. Of all the artists profiled in Born Into the Gig, Ms. Withers seems both closest to and most in awe of her famous father, hit-maker Bill Withers.

Producer Tamara Weiss of Chilmark — Jeanna Shepard

In what Mr. Heilbroner said was Mr. Withers’s last in-depth interview before his death in March of this year, the singer-songwriter makes sure his daughter has no illusions about the path to success.

“There’s no birthright to this,” Mr. Withers says. “It ain’t about impressing me; you impressed me when you came out the womb. This is a worldwide competition.”

His words encapsulate a major theme in the documentary: No matter who your parents are, you’re responsible for your own career.

“We’ve learned a lesson in making this film: Keep your expectations of grandeur in check,” Mr. Heilbroner said. “It’s such a tough marketplace out there.”

Ms. Simon, Stephen Stills and Ms. Sanson and members of Mr. Marley’s illustrious Jamaican musical family are among the other elders interviewed in Born Into the Gig. James Taylor declined to take part in the documentary, although he is seen and heard in archival snippets.

“I think he will tell his story when he’s ready to tell his story,” Ms. Weiss said. “This wasn’t the right time.”

Born Into the Gig is a detour from the customary work of Ms. Davis, a longtime filmmaker, and Mr. Heilbroner, a former Manhattan prosecutor turned author and director. For the past 20 years they have specialized in documentaries on social justice matters, including the Academy Award-winning short Traffic Stop and the feature-length Say Her Name: The Life and Death of Sandra Bland, both of which are currently available on HBO.

But it’s not their first music film. The couple both play instruments and sing — Mr. Heilbroner even worked as Ms. Simon’s guitarist for a while — and their 2005 documentary Pucker Up follows six competitors at the Annual Whistler’s Convention in Louisburg, N.C.

Born Into the Gig offered them another chance to lighten up.

“Most of our films are about serious, pressing issues of the moment,” Mr Heilbroner said. “When Tamara came to us, it seemed like such a lovely departure.”

Married since 1987, Mr. Heilbroner and Ms. Davis are also the parents of two adult children, who grew up on the Vineyard and attended Island schools. Both children worked on Born Into the Gig, 25-year-old Quentin Heilbroner in graphics and 22-year old Katrina Heilbroner on transcriptions. They also critique their parents’ works in progress, Ms. Davis said. “Both of them are excellent viewers.”

Longtime filmmaker Kate Davis. — Jeanna Shepard

Making a film about adult children, the filmmakers said they found themselves reflecting on their own roles as parents.

“I’m just aware that my sheer existence is having an effect on my two kids,” Ms. Davis said. “They can’t help but compare themselves to us, even on a deeply unconscious level, and that never goes away.”

“I think it’s also relatable to people who are not in the music business, just as children of their own parents and how they fit, how they feel and how they measure their own success,” Ms. Weiss said.

Born Into the Gig played several film festivals, including in Nashville and the Bahamas, before the Covid-19 pandemic closed theatres. Its virtual run in the FILMusic festival has ended and Mr. Heilbroner said several distributors have made offers to release the documentary.

Meanwhile, the film’s soundtrack of classic tracks by the older generation and new music by the cast, including Ms. Withers’s haunting cover of her father’s Ain’t No Sunshine and Mr. Marley’s hit Cry to Me, is available for listening at and as a playlist on the Spotify music streaming platform.