Photograph Courtesy Steve Brainard

Judy was never a “dulcimer girl,” as she put it. She was folky, but she was also bluesy, brawny, and brainy, a complicated artist who was tough to pigeonhole.

NEW THIS WEEK: Cover story author Barry Alfonso reads his story, "Game Girl: Remembering Judy Henske, Queen of the Beatniks." Click on the link at beginning of cover story in the clickable Reader flipbook to hear the 26-minute audio of Alfonso's reading.

The late, great Judy Henske – singer, songwriter, journalist, visual artist, raconteur and force of nature – arrived in San Diego in 1959. She quickly became a mainstay on the stages of the city’s coffee houses, belting out ballads that could both shake the walls and rile the neighbors. Like so many others, she made her mark and moved on. Unlike so many others, she re-appeared 30 years later, both at local folk festivals and in the pages of this publication. Her work in the Reader gave readers a glimpse of her sly humor and formidable intellect — but only a glimpse.

Photograph Courtesy Steve Brainard

Judy Henske was a six-foot-tall woman from Chippewa Falls, Wisconsin. Her physical size alone was enough to make sure she always stood out in a crowd, but the truth is, everything about her was big. Her singing voice was loud and passionate, especially when she used it to render an ancient murder ballad or a classic blues number. Same went for her personality: she matched her on-stage earthiness with a love of poetry — you might say she combined the gutsy kick of Bessie Smith with the killer wit of Dorothy Parker. Her broad range of intellectual interests and hunger for knowledge made her both fun and formidable in conversation. Producer/composer Jack Nitzsche dubbed her the Queen of the Beatniks, a title she wore with self-mocking swagger, but there really was something more-than-ordinary, even royal, about her.

I was lucky enough to get to know her over a quarter-century, but it wasn’t enough. I wish could hear more of her amazing stories, keep grappling with her quirky but shrewd insights, and laugh with her about the arbitrary thrills and cruelties of show business. I first saw her while browsing the used LP bins at downtown’s long-gone, much-missed Arcade Records. There she was on the cover of her 1964 album High Flying Bird, a big-boned chanteuse in a white sweater, jeans, and boots, standing on a rocky beach that could’ve been anywhere between Torrey Pines and Tamalpais. I recognized her name from folk anthologies, but there were no ethereal, Joan Baez-y, damsel vibes about her. Judy was never a “dulcimer girl,” as she put it. She was folky, but she was also bluesy, brawny, and brainy, a complicated artist who was tough to pigeonhole.

I began to understand her better after I met her in the flesh in 1994. At the time, I was working on projects for Rhino Records, digging through the back catalogs of 1960-era artists and dusting off choice cuts for reissue. The label gave me the go-ahead to compile a “best-of” Judy Henske collection, so I thought I’d begin my research by contacting the artist herself. We agreed to meet at a restaurant in LA’s Studio City. When she finally walked in the door, I immediately knew it was her — not so much by her height or the characteristically intense look on her face, but by the way her presence immediately filled the room. Judy naturally commanded attention, even more so when she began to speak. But she wasn’t full of herself. She was too darkly funny for that, and too curious about other people — especially their quirks and foibles.

That curiosity was part of why she had begun taking on writing assignments for the Reader. Oddly, she had also begun performing live again, after a nearly 20-year hiatus. Starting a new career while returning to another might sound a little scattershot, not very strategic — but that’s how Judy always approached things. She plunged into anything that interested her, laughing all the way. “I was always game,” she told me. “I am a game girl.” Judy never played “the game,” though. Or at least, never by anyone else’s rules.

Storytellers can be reticent when it comes to their own lives, and so I never got the complete version of The Judy Henske Story. It felt like there was always another unlikely encounter or bizarre misadventure to add to the mix. But it began something like this: Chippewa Falls was a pleasantly nurturing, if confining, place to live for young Judy. Raised by Dr. William and Dorothy Henske, she grew up a well-behaved Catholic girl in a comfortable upper middle-class home. The nuns who taught her at McDonnell High recognized her talents in visual art and especially singing. Judy loved to tell the story of how Sister Thecla taught her to project her voice by standing on her diaphragm while she lay on the schoolroom floor.

Friends knew that Judy wasn’t meant to simply marry a local boy and settle down. Her uncle Francis Beauchesne Thornton — a Jesuit priest and published poet who served as the book editor of the Catholic Digest for many years — kindled in her a deep love of literature. She recalled, “Uncle Frank said to me very seriously, ‘I hope you are not going to hide all of your light under a bushel by becoming something easy. Always use your talent.’ I always had that voice in my ear. And I was lucky to have someone who was that strong in my life.”

It wasn’t all love and support. Her father developed a fondness for tranquilizers, a habit that led his wife into serious drug abuse. Her mother’s love of prim table manners, smart clothes, and proper deportment hid family secrets that extended to Judy’s paternity. (She found out as an adult that one of her aunts was her actual birth mother.) Judy would retreat to her bedroom with her friends, try out routines from joke books, and listen to records. She knew there must be a better life waiting after high school, despite the talking-to she got from Mom and Dad before attending Rosary College in Illinois: “You’re not going to do anything with your talent. Take classes in things you can fall back on.”

Judy shared this photo of herself with the author in 1994, while they were working on a “best-of” Judy Henske collection with Rhino Records.

Photograph Courtesy Barry Alfonso

She ignored the advice, and tried majoring in art and voice, but found she couldn’t keep up with the required basic courses. Asked to leave Rosary on a day’s notice during her senior year, she followed a boyfriend to Oberlin and then to a Quaker commune in Philadelphia. Along the way, said boyfriend introduced her to folk music. Artists like Pete Seeger and Odetta were leading a major folk revival in the late ’50s, combining a love for traditional balladry with left-leaning political activism. Judy embraced the music, but turned away from the politics. “I met a lot of folkies, very serious political people,” she recalled. “After a month of that, I was sure that wasn’t who I was. The thing is, I kept cheering up all the time. To change the world, you’ve really got to be depressed. And I have a pretty buoyant nature — that isn’t the right one for changing the world.”

It seems fitting that Judy’s buoyant nature sent her floating to San Diego. Her aunt Eleanore was one of many military wives who moved to San Diego County during and after World War II. One day, Judy arrived at Aunt Eleanore’s house in Clairemont in her boyfriend’s MG, ready to try her luck singing folk songs in local clubs. “I said, ‘I’m not, not, not going to be in the adult world,’” she told me. “I didn’t want to sit in an office typing — I wanted to play!” Over three decades later, Judy recalled those early, scuffling days in one of her Reader submissions: “In 1960, I was living in Mission Beach over by the amusement park…It was a ramshackle cockroach-infested tourist court so close to the old wooden roller-coaster that when you were talking on the phone, you had to stop until the coaster went over that first big dip and came down again. The screams of the riders, the clackety-clacking and thundering of the steel wheels were that loud.”

The nuns who taught Judy at McDonnell High recognized her talents in visual art and especially singing.

Armed with her trusty banjo, she started gigging at beachcomber dives and beatnik hangouts around town. One of the more pungent venues was the Mantiki, a beer bar in Pacific Beach: “The Mantiki was a bar where the ‘Haw haw, gimme another one and put a head on it!’ crowd hung out. It was like a club for bums and beatniks. Sometimes, sailors on leave would wander in. These three different groups didn’t always get along, so there were fights. When the beer mugs began whizzing through the air, you’d just take the mic as far down as it would go, lie down on the stage and keep singing ‘Run, Come See Jerusalem,’ hoping for the best.”

The coffeehouse scene was more copacetic. She started playing weekends at the Zen Coffee House and Motorcycle Repair Shop, a haven for oddballs at the corner of India and Broadway. Judy recalled, “It had an interesting clientele. There were these SDG&E employees and there were these guys who’d just gotten out of prison. Like real criminals.” She frequently held forth at the Upper Cellar, a popular hipster hangout at 6557 El Cajon Boulevard. Judy would wail at the espresso-sipping crowds as her foot punished the stage with hammering stomps. “When I stood up, my legs would shake a whole lot out of fear. So, to take attention away from my wobbling legs, I stomped my foot. Terror and fear started it, but it translated into some kind of aggression, which it wasn’t at all.”

Aggressive or no, Judy came on strong. “She sang so loud that the neighbors up and down the block complained,” Upper Cellar owner Bob Stane told me in a recent phone call. “Her voice was just huge. I would ask her to tone it down a little bit, but she really couldn’t do that. Her voice was just on ‘10’ all the time.”

In between her treatments of barrelhouse blues and murder ballads, Judy would veer off into absurdist vignettes that mocked the seriousness of the folk revival. “This is a little children’s song that comes from the red-light district of Chicago,” she would quip when introducing the nonsense-rhyme ditty “Hooka Tooka,” thus puncturing any reverence for folky traditionalism that might have lingered in the room. Judy slipped easily into sweetly outrageous standup — a sort of real-life model for The Marvelous Mrs. Maisel, a pioneering female comic in an era where they were rare birds indeed.

And then she left for brighter lights. Judy headed to Los Angeles in 1960, where she became a featured performer at the Unicorn coffee house on the Sunset Strip, opening for Lenny Bruce and other notables. She landed touring gigs across the West, and did a brief stint as a member of The Whiskyhill Singers, an ill-fated quartet formed by ex-Kingston Trio member Dave Guard. In 1962, she came back to town to play in Gypsy at the Circle Arts Theater, an in-the-round venue on Clairemont Mesa Boulevard. “I played Electra, one of the strippers in the show,” she recalled in a 1994 Reader interview with writer Abe Opincar. “I shared a dressing room with two of the other strippers — Jolene Lontere and Gaby De Lys. It was quite an experience being in the dressing room with the two of them. I remember as they’d undress, Jolene and Gaby would glare at each other’s breasts in jealousy…”

Perhaps despite that career detour, Elektra Records signed Judy to a solo contract in late 1962 and attempted to refashion her as a classy lady balladeer, retaining her humor but scrubbing off the bohemian grit. The label chief and his wife stuffed her long hair under a Louise Brooks black wig and decked her out in slinky evening gowns. She moved to Greenwich Village and performed a series of high-profile shows at in-crowd clubs like the Village Gate. Jazz greats Herbie Hancock and Clark Terry played in her backup band. The New York Times and Newsweek gave her favorable write-ups. Stardom seemed to beckon. But when she talked to me about those days, Judy emphasized the fun she had, not the money and fame that were dangled in front of her.

She had a knack for attracting other smart and talented people; many of them became friends and/or lovers. A young stand-up comic named Woody Allen was among them. They became close during mid-1963 and had something resembling an affair. It ended the following year. Judy was always a bit cagy when talking about Woody, who shared the bill with her at club dates in New York and Chicago. She did confirm to me that they delighted in each other’s lightning-fast repartee and love of esoteric knowledge. “One time, we were in Woody’s apartment,” she said. “He had gotten a new dictionary that was on a dais. With the powers of our mind, we were trying to get the pages to turn. I think we sat there for an hour, grunting and straining.”

Judy performing at the Buddhi in Oklahoma City with Steve Brainard in August, 1961.

Photograph Courtesy Steve Brainard

A decade later, Allen based the title character of Annie Hall at least partially on Judy. The similarities were undeniable, right down to Annie’s hometown of Chippewa Falls. Like Judy, Woody’s heroine was a singer with a footloose, attractively kooky demeanor. “He got a lot of his story from me,” Judy said. “Not the screenplay, but the personality of that girl.” She had mixed feelings about it all — certainly, she wanted to be known for more than serving as the model for a character created and embodied by other people.

Besides testing out her psychic powers with Woody, Judy plunged into a dizzying and somewhat dubious array of projects in those heady days of the early ‘60s. Tapped to be a regular on Judy Garland’s TV show, she was dismissed after one episode for refusing to take part in a skit making fun of farmers. More enjoyable was her role in Hootenanny Hoot, a B-grade folk exploitation movie also featuring Johnny Cash. Then there was her would-be star turn in Gogo Loves You, an Off-Broadway musical cooked up by Anita Loos (of Gentlemen Prefer Blondes fame) that closed after two performances. Judy emerged from these semi-successes and outright disasters as cheerful as ever, laughing in the face of opportunity and failure alike. “I didn’t want to become some giant star,” she told me. “If you’re a giant star, all you do is work and read other people’s dumb lines. I didn’t want to be doing that, I just wanted to be kind of a minor blip on a screen. But I would be known as being unusual. That’s all I wanted.”

After leaving Elektra, Judy made a series of albums and singles for Mercury and Reprise, but they failed to place her in a marketable musical context. Her most notable project in the late ‘60s was Farewell Aldebaran, a collaboration with her singer-songwriter husband Jerry Yester. An eccentric psychedelic baroque-folk excursion released on Frank Zappa’s Straight label, the album marked Judy’s emergence as a lyricist of poetic refinement and mordant wit. Sad to say, Farewell Aldebaran failed to find a large audience, though it did manage to earn an enduring cult following. After that, Judy and Jerry formed a band called Rosebud, which released one album in 1971, then promptly broke up. Judy’s marriage ended around this time as well. Remarried to Craig Doerge, keyboardist for Jackson Browne and Crosby, Stills & Nash, she concentrated on raising her daughter Kate, cooking hearty Midwest-style meals for her family and writing songs at home. “I’d had enough, so I withdrew,” she said.

But once Kate was safely off to college, Judy and Craig began plotting her re-emergence into the spotlight. She was encouraged by the attention author Andrew Vachss brought her when he made her a sort of ominous leitmotif in his crime novels. Vachss connected with the darker shadings in Judy’s voice and repertoire, making her a reoccurring presence in his books, from 1985’s Flood onward. He was responsible for introducing Judy to his friend Judith Moore, book editor for the Reader. She became the subject of an extensive Reader profile and then started writing for the paper herself. She pitched a flurry of story ideas, some of them inspired by random interactions with strangers. Judy’s relentless curiosity and ability to find absurdity and poignance in just about any earthly endeavor made her a natural for alternative journalism.

A prime example of her skills as a reporter was displayed in her April 25, 1996 article about San Diego’s pigeon-racing community, which she discovers through a chance encounter. At the story’s outset, she creates a mock-film noir atmosphere that both arouses interest and tints the scene with comedy, much as Judy would set up dire murder ballads with smart-alecky intros on stage…

I was riding on the 8:35 a.m. train from L.A. to San Diego. About halfway between Oceanside and Solana Beach, we had pulled to a side track to wait for the southbound Amtrak to pass. Suddenly I started smelling vodka.

As I began to smell vodka, I also started having an uncomfortable feeling that I was being stared at. I put down my book and glanced around. Then I saw an eye looking at me from the space between the two seats directly in front of me. I watched as whoever it was turned his head sideways so he could look with both eyes. There was a scuffling sound as he knelt backward on the seat. Then he popped up like a demigod in a James Stephens folktale. Always on the lookout for demigods, I paid immediate attention.

He gripped the back of the seat with one hand, and in the other he held a large, clear-plastic glass filled to the top with ice and a colorless liquid. He was pale, well barbered, and imperially slim, possibly 35 or 40, and had the kind of wild light in his eyes that only magical powers or a stiff dose of vodka before noon can give you. His name was Vito. We began to talk...

There’s a sort of hip, New Journalism raciness to Judy’s prose that suggests Tom Wolfe, but the more I dug into her writing, the more I was reminded of the droll confiding tone of old-time New Yorker wordsmiths like A.J. Liebling: We’re sitting out on the patio of Chef’s restaurant in Arcadia, a few miles from Santa Anita racetrack. Why here? How here? The day before, at the track, while digging the Hollywood Park, Bay Meadows simulcasts, I bumped into my cash-only-no-checks dentist at the $100 window where a couple other little old ladies and I were placing a Charles Bukowski Memorial Bet for a sick friend. A 20-to-1 shot in the third race. I told the dentist about my new interest in pigeon racing. He set me up with the interview. Fifteen pigeon racers. Everybody needs a dentist.

A bit zanier was a February 15, 1996, contribution to the Reader’s Music Scene section chronicling a tour of San Diego County businesses (including Foot Locker, Coco’s coffee shop, and the First Step Pre-School) to check out their background music. Along the way, she referred to Andrew Lloyd Webber as “The Grand Gunkmeister of Bozo-Theatro, who plies us with glistening musical goblets” and remarked that the show biz treasures at Planet Hollywood resembled “ritual objects in a cross-referenced Victorian Bustle-Religion and Cargo-Cult.” Judy loved to cultivate colorful and eccentric phrases like hothouse flowers, riffing on her vast store of acquired knowledge and personal experience.

In between such flights of fancy were slightly more serious meditations on weighty subjects. In an essay submitted to the Los Angeles Mission (a Catholic monthly), Judy examined her complicated yet unshaken connection to her faith. She contrasted the exalted sights, sounds and scents of a traditional Catholic service with the blandness of modernism (an indicator of “creeping Protestantism”). Judy reveled in the shimmering colors of stained-glass windows, the smell of incense and beeswax, the transformational mystery of worship. She closed with a bohemian’s benediction: “All the old ideals, the places and people and the things that were so new and so perfect to us in childhood, deep in our lives we continue to search for them, and finding them, hold them close until we journey home.”

I accompanied Judy on one of her Reader assignments in mid-1996. Her longtime friend John Haynes drove her down from Pasadena to interview a junkyard dog trainer. Judy — who loved animals of all varieties — was excited to write about the bond between canine and human in such a hardscrabble setting. When the three of us arrived at the yard on Nirvana Avenue(!) in Chula Vista, the chained-up harshness of the dog’s life convinced her not to write the story. We spent the rest of the day having lunch at a Mexican restaurant and arguing over the merits of John Denver. (She was a fan; I was a skeptic.)

By the end of the ‘90s, Judy was back to concentrating on music, releasing Loose in the World, a reaffirmation of her singer-songwriter talents that featured the nostalgic “Wish I Had My Old Guitar,” a line from which opens this story. She also returned to performing with a series of well-regarded shows, put out another CD of new material (She Sang California) and finally received her long-awaited “best-of” retrospective when Rhino released her Big Judy: How Far This Music Goes two-CD set in 2007. Declining health and fading eyesight didn’t stop her from working on songs and embarking on her memoirs, but the latter remained unfinished when she died at age 85 in April 2022.

I was lucky to have many long and delightfully rambling phone conversations with Judy over the last two decades of her life. Just about anything was fair game in these chats: music, food, family, literature, metaphysics, mortality. She always recalled some previously untold anecdote about Pauline Kael, Phil Ochs, Eve Babitz, Shel Silverstein, or some other famous, infamous, or obscure person. And she always took an interest in what I was up to, encouraging me with positive words that were savvy, sympathetic and bullshit-free.

Late in life, Judy reflected on what mattered most to her. “It doesn’t make any difference to me if I’m not the most famous person on earth or if anybody remembers me in ten years,” she said. “That’s not the point. The point is that, in your life, what you hope to find is some kind of self-realization so that you know who you are -- you know who it is you are left with, with those aching bones and the eyes that can’t see. So that you know who that is.”

Who was Judy Henske? She was the young folkie playing guitar under the stars in Mission Beach. The foot-stomping Beatnik Queen who took L.A. and Greenwich Village by storm. The wife and mother who stayed true to her personal art. The journalist with the eye for the incongruous and the otherworldly. And she was my dear friend.

Editor’s note: Mr. Alfonso is currently at work on a full-length biography of Ms. Henske.