Helen Cromwell & Robert Dougherty
Originally published in 1966, Good Time Party Girl is the life story of infamous Milwaukee tavern owner and madame Helen Cromwell as relayed to her friend Robert Dougherty towards the end of her life. Don’t be fooled by the book’s austere, old-timey cover: inside is a bumping, animated romp through the 1900s as told by a delightfully spunky woman seemingly unhindered by societal notions of what a woman “ought” to be.
Typically, women’s stories from the Victorian era through the 1950s dwell on their oppression and limited options for sexual fulfillment, career, and family life. Similarly, sex workers then and now are generally portrayed as impoverished victims of abuse and trafficking. Women “of the past” are too often painted as tied-up victims imprisoned in yellow-wallpapered rooms until they stick their heads into ovens or walk listlessly into the ocean.
By contrast, Cromwell’s is a breath of fresh air, the picture of self-actualization and agency. She was anything but a victim of circumstance: born into a relatively wealthy Indiana family, she eloped with an Irish immigrant and spent most of her 20s as a dedicated housewife. Only after tolerating years of her husband’s cheating did she abandon him and head west to start a new life.
Through the glamor and glitz of her chosen life as a professional escort cavorting with the Gilded Age’s robber barons, Cromwell’s business aptitude is the true star of the story. She was often working two jobs: clothing saleswoman by day, escort by night. She developed her sales skills, her expensive taste, and her clientele while working at clothing shops and department stores that catered to society’s upper echelons. The day job, she noted, did not pay enough, prompting her to continue sex work. Sprinkled into her stories are interesting factoids and intriguing, if terrifying, run-ins with crime syndicates as she rubbed elbows with infamous figures of American history in the Jazz Age’s establishments.
The tragic irony of Cromwell’s story is the number of times she attempted to have a “normal” and “respectable” life. She spent her 20s trying to save a failing marriage; years later, she fell in love with a WWI vet from Hyde Park and quit sex work to be with him, only for him to die a year later of complications from mustard gas he inhaled in the war. She married several more men in good faith, only for them to continue to die suddenly or abandon her.
Milwaukee’s Sunflower Inn, a speakeasy she turned around and ran for decades, became her home and her purpose. It was her business savvy and fiscal agility that kept her afloat through all the personal turmoil, cementing her in the Midwest’s imagination.
“Dirty Helen” Cromwell deserves her own biopic. An antiheroine of our own, she embodied the Midwest’s industriousness, ingenuity, and resilience—and our love of booze. In fact, Great Lakes Distilling released “Dirty Helen” bourbon in honor of the book’s publication. Read about how Christina Ward, a Milwaukee native, revitalized Cromwell’s story for the 21st century here, and purchase Good Time Party Girl at your favorite local bookstore.
Good Time Party Girl: The Notorious Life of Dirty Helen Cromwell, 1886–1969 is available at most bookstores and through the Feral House website.