Meet Holly Penfield, “a cross between David Bowie and Liza Minnelli”

“From eight years old, I wanted to be a nightclub singer,” recalls the willfully eccentric Holly Penfield, a native of Orinda.

Now a fixture on the London cabaret scene, she will play a rare U.S. engagement at Feinstein’s at the Nikko on May 4 and 5.  “I took ukulele lessons and then guitar when my hands were big enough. I wrote my first song at twelve, to earn a Campfire Girls badge.”

Penfield’s late father was a serious music lover, and when his daughter’s aptitude and focus, he arranged for her to take singing lessons with Judy Davis. The esteemed Bay Area vocal coach had earlier worked with Barbra Streisand, Judy Garland, and Frank Sinatra among others.

With Davis’ assistance, 14-year-old Penfield booked a series of promotional events for Macy’s, singing at stores statewide and cutting a giveaway 45-RPM record that still, to Penfield’s shock and delight, shows up in the hands of autograph-seeking fans at her infrequent Bay Area performances.

In her late adolescence, Penfield—now sixty something— felt increasingly out of sync with the other students at Campolindo High School.

“I was telling my counselor I would kill myself if I had to keep going to school,” she recalls. “It wasn’t right for me.”

Ostracized as an oddball by many of her schoolmates, Penfield—who Simon Cowell has called “a cross between David Bowie and Liza Minnelli”— was celebrated by her parents, who unflaggingly supported dreams of musical stardom. They agreed to hire an at-home teacher and send Holly to a psychiatrist.

And Judy Davis arranged a nightly gig for her star pupil,  singing at the Roaring Twenties, strip club in North Beach. “I didn’t have to take my clothes off, but the girls did all around me.”

“My parents were over the moon!” recalls Penfield

Around the same time, Penfield began to listen to the contemporary music of the early 1970s. “When I first started paying attention to Laura Nyro and Joni Mitchell, that was it,” she recalls. “I wanted to write and perform my own music.”

Penfield assembled a band and began playing a wide variety of venues in the Bay Area’s booming rock scene, ultimately headlining at the Keystone Berkeley and Winterland, noted trolling grounds for record companies’ A&R men.

“In the end,” recalls Penfield, “I got a deal with Mike Chapman, who had become famous for producing Blondie and The Knack. Chapman immensely believed in my talent. But he was a lousy businessman. A great producer, but he didn’t really know how to run a label.”

“I was up against Debbie Harry and Olivia Newton-John. I was really quite an arty little writer. But the Laura Nyro thing had passed.  But I don’t regret any of it. I’ve had an extraordinary life and chances are, it wouldn’t have happened without those early years.”

While making the rounds in the rock scene, Penfield met -and ultimately married- Scottish producer and composer Ian Ritchie, perhaps best known for producing Roger Waters’ first post-Pink Floyd solo album. The couple eventually settled in London where, in her early forties, Penfield decided to revisit the standards she’d learned as a girl.

“I can’t explain why my own songs never caught on, but I was too far gone as an entertainer to stop. I started playing little venues in London and eventually, I was doing five nights a week. I developed a really big gay following.”

“I didn’t take myself so seriously any more. I  just let go of my former ambitions and performed. I was in my late forties and it felt like I was freed. ”