Making a groundbreaking album for a mobbed-up record label wasn’t on the syllabus for most Vassar undergrads in the mid-1970s, but Deidre McCalla has always followed her own path.

Already a familiar face on the Greenwich Village coffee house scene, the teenage singer/songwriter quite suddenly found herself in a Manhattan studio recording her debut album Fur Coats & Blue Jeans for Mo Levy’s Roulette Records, which for several decades served as the Mafia’s primary recording industry redoubt. 

Largely unaware of the label’s reputation for siphoning money away from artists, McCalla was far more concerned about retaining control of her songs, as “the whole experience of recording an album in that slick New York industry way took tons of stardust out of my eyes,” she said in a recent phone call from her home in Riverdale, Georgia. In a rare trip back to the East Bay, where she lived from the mid-1980s to the mid-‘90s, McCall plays the Back Room Sunday afternoon celebrating the release of her first new album in two decades, Endless Grace.

Her new songs are full of hard-won wisdom leavened with gentle wit. She’s a composer who crafts winsome melodies that suggest deeper currents running alongside her carefully observed lyrics. Working in a more acoustic, folky vein than on previous releases, McCalla has circled back to her initial sources of inspiration that grabbed attention half a century ago.

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Looking to grab a piece of the burgeoning singer/songwriter market in the early 1970s, Roulette paired the Vassar sophomore with arranger Lee Holdridge, whose career was rapidly ascending via his work with pop acts like Neil Diamond and John Denver. Used to performing solo, McCalla found Holdridge’s elaborate studio arrangements disorienting, and kept missing her cue to start playing. 

The studio band “started one of my tunes and I didn’t come in,” she recalled. “They started again, and I still didn’t come in. Holdridge came over the speaker to ask what was wrong and I was practically in tears. It was my song and I didn’t even know where I was supposed to start playing anymore. After that the rest of the tracks were done with me and the rhythm section.”

Making the album was one hurdle. Navigating the racial assumptions of the American music market posed a whole different challenge. With era-defining songwriters Bob Dylan, Joni Mitchell and Paul Simon serving as her muses, she worked on developing her own lyrical vision. Roulette handed the album off to a young radio promotion guy who drove across the country, station to station. The report McCalla got from the road was predictable and disheartening. 

“What he found was with my photo as a Black woman on the cover the white stations just immediately discarded the album, saying ‘We don’t play Black music,’” she said. “The Black stations, when they put the music on, said I don’t have the typical Black voice they were programming. ‘She sounds white.’ I don’t know if I ever consciously felt I had a choice. I could only do what I did. It’s not like I’m going to suddenly have the voice of a Patty LaBelle or Diana Ross.” 

Releasing a nationally distributed album while your peers are studying for midterms is impressive, but McCalla doesn’t recall being much of a campus celebrity. “I was already playing coffee houses and was somewhat known as a campus activist through my work with the anti-war movement,” she said. “The only thing I became notorious for was my senior project as a theater major, when I decided to direct a play by Susan Miller about a woman coming out. The word spread on campus there was a lesbian kiss and all the performances were sold out.” 

What was titillating at Vassar didn’t work to her advantage on a 1970s music scene that still expected gay and lesbian artists to stay in the closet. While looking for another label to release her music McCalla worked on improving her craft, studying jazz guitar at the Wisconsin Conservatory of Music. She returned to New York but after several years, at the urging of photographer Irene Young, she decided to trade Gotham’s grit for a new start in Oakland in 1983. She wound up living in a house in Grand Lake with string player Robin Flower. 

In the mid-‘80s the women’s music movement was cresting, and the Bay Area-based Olivia Records was the primary outlet for artists like Cris Williamson, Teresa Trull, Linda Tillery, and Mary Watkins. McCalla fit right into the scene, releasing three albums for Olivia, starting with 1985’s Don’t Doubt It. But in the fall of 1994, with a toddler to take care of and no family around to help out, she decided to settle near her parents, who’d moved back to Georgia. 

McCalla worked steadily on the college circuit, often touring with her son. When it was time to start school, she didn’t see the local district as a viable option for a Black boy and “discovered homeschooling, which changed my life,” she said. “I did not want him educated in the South. I could teach him.” The situation worked well through middle school, but by his mid-teens he was lobbying hard to enroll in high school. She found one of the best public schools in the state and gave up touring. 

“That was a big lifestyle change for us,” she said. “I didn’t give up playing completely, but did wind up getting a job at Starbuck’s, where I worked for 11 years. I often tell people it was the best crap job I’ve had. There was a lot of scheduling flexibility, so when I had a gig you could get someone to cover your shift.”

With the encouragement of her old housemate Robin Flower, McCalla started teaching guitar and songwriting, “and besides going to music school that’s the single most important thing I’ve done to improve,” she said. “I’ve become a better player because of teaching my students.”

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Her last album, 2003’s Playing For Keeps, was produced by Laurie Lewis and Teresa Trull, and features a stellar cross section of Bay Area musicians, including guitarists Nina Gerber and Jim Nunally, violinist Chad Manning, pianist Barbara Higbie, and percussionist Vicki Randle. A deliberate composer, McCalla gradually built up a sheaf of new songs she wanted to document, though financing a new recording wasn’t on the table until a longtime fan came forward as a patron. 

Photographer Irene Young, who’s played a historic role documenting the women’s music scene since the early 1970s, urged McCalla and Julie Wolf to work together. A multi-instrumentalist and veteran producer with a studio in the Fantasy Building, Wolf saw the new project as an opportunity to complete a circle, as she’d followed McCalla’s music since her older sister studied with her at Vassar. She ended up producing half of the tracks on Endless Grace, while the other half were recorded in Nashville with producers Dianne Davidson and Larry Chaney.

Julie Wolf and Diedre McCalla. Credit: Irene Young

“Deidre is such a light, so kind and smart and dear and she writes really beautiful, thoughtful songs,” Wolf said, while noting that Endless Grace is only her sixth release. “It’s a precious discography, and it’s not a small thing that she decided to make another record. But she’s got fans everywhere. I was working with Kristen Henderson from the band Antigone Rising and mentioned I’d been recording with Deidre and she started singing a bunch of her songs.”

Wolf will be joining McCalla Sunday at the Back Room, along two other players who contributed to Endless Grace, drummer Nino Moschella, who also engineered the Bay Area tracks, and supremely versatile bassist Daniel Fabricant, “which opens things up a lot,” Wolf said. “I’ll be playing some piano, and I’ll have my Nord keyboard, which can have Fender Rhodes sound. And I love playing guitar and six-string banjo, when people let me. I’m just excited to lift Deidre up.”

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Andrew Gilbert

Freelancer Andrew Gilbert writes a weekly music column for Berkeleyside. Andy, who was born and raised in Los Angeles, covers a wide range of musical cultures, from Brazil and Mali to India and Ireland....