The Dirtiest Mouth in Milwaukee: The Legend of Dirty Helen

by

 “ Milwaukee in the late 1920s was a town of unblushing, brawny vice rammed through with scents of European cooking, cheap perfume, and workers’ sweat… the city’s gentry tried to mislead themselves into thinking of Milwaukee as fragile and culturally dainty, but it was as strong as an American buffalo.”

                                                - from Dirty Helen, By Helen Cromell

“Dirty Helen” Cromell was a legend of the Milwaukee nightlife, known to have the dirtiest mouth in town. Helen ran the barebones Sunflower Inn (1806 West St. Paul Street) for over thirty years, a favorite stop for traveling salesmen, politicians, athletes and the occasionally celebrity, including Gloria Swanson and Liberace. The Sunflower was a 20’ x 25’ room with a potbellied stove, a bar, and little else. There were no chairs or stools, and customers were expected to stand or sit on the floor. The ornamentation consisted of a huge nude oil painting behind the bar - Helen liked to tell visitors it was her, from back when she was “hustling in the Yukon .” Helen served only bourbon or scotch and mixed them only with water. A request for a cocktail inspired a tirade of filth from the hostess, but if Helen liked you – and she liked a lot of people – she’d afterward call you a “good sport” and pour you a drink on the house.

It was her time in Milwaukee that made Helen famous. In her raucous self-titled memoir, she tells her life story with wit, sass, and no shortage of dirty passages. Only the last 70 pages of the book cover her time in Milwaukee , but the place she presents is unlike any other published accounting of the city (well, except for maybe this one). Her story starts in rural Indiana , where she was born in 1886. She falls in love with a boy whom her father hates, learns about sex from an older cousin (“there were no flies on her fast ass,” Helen writes), marries the boy, gets disowned, and ends up an unhappy housewife in Cincinnati . Pregnant with her second child, she learns her husband has been carrying on with a prominent Cincy madam. Taunted by the other woman over the telephone, Helen goes to her apartment, claws her face raw, and throws her head-first down a flight of stairs. In her rage, she learns that can make her own way and doesn’t need to play anyone’s fool. She starts turning tricks and sees the world. She operates in Arizona , Chicago , and San Francisco . Some of her clients fall in love with her and lavish her with gifts and cash. She falls in love herself here and there – enough for a half-dozen marriages – but her love stories always have tragic endings: heartbreaks, suicides, and loneliness. Helen writes of knowing gangsters in Chicago . She says that Al Capone had her turn around one of his low-end whorehouses. It was her job to watch the door and keep track of the cash. The men were to pay her $1.20 a turn, a buck for the girl, ten cents for the guard outside the house, and another dime “for the towel.” If you lose track of how much money you should have, Capone tells her, just count the towels.

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In Superior , Wisconsin , Helen has a much more dignified role as madam of the area’s finest brothel. She makes good cash, but is driven away from the business when her latest love is pinched on a dope smuggling charge and hangs himself in his jail cell. She is heading back to Chicago on the train, when she meets a salesman from Milwaukee . He says that the city might be a good fit for her. With nothing of particular importance waiting for her in Chicago , she agrees to give Milwaukee a look. She would stay there for the next 43 years.

Helen made haste in Milwaukee . She bought an old dump of a speakeasy and went back to tricking to earn the cash to fix it up. She was 40 years old by the time she hit the city’s downtown red light scene but claimed to have been the area’s most popular working girl. Her fiery red hair, sleek dress, and ample figure – she sometimes said that her chest was so large, she had to wear a cast iron bra – earned her as many as 25 clients a night. Soon, her Sunflower Inn – so named for the sunflowers that grew in its front yard – was one of the top speakeasies in town. After Prohibition ended, it became the little hole in the wall that everyone in town knew about and everyone stopping here wanted to see. The stories of her foul mouth became so legendary that she learned to perform on command. An exchange between her and her piano player – he’d get drunk and she’d pound the bartop with a cudgel, threatening to crack him a good one if he didn’t clean up his act – became a regular routine. But for a woman who had never been able to stay in one place very long, Helen seemed to get as much from Milwaukee as it did from her.

Helen made a lot of money in her various trades, but it always went fast. In Milwaukee , she had a soft spot for Marquette kids down on their luck. She couldn’t even remember how many tuition bills she paid, hating to see a kid quit school just because he couldn’t get the money. One of these cases was, according to Helen, a young man named Joseph McCarthy. She even claimed to have convinced him to drop out of the engineering program and study law.

By the late 1950s, it seemed that Helen’s luck in Milwaukee was running out. She had money problems and lost the bar (she claimed to have been swindled in a bad loan deal), leaving her with nothing more from the Sunflower than the big nude painting. Dirty Helen only covers her life up until about 1961. She downplays her troubles, but newspaper accounts from the same era depict a slow and sad decline for the woman whose company everyone in town once fancied. She owed thousands in back taxes, leading the government to cut off her monthly social security payments. The year after she lost the bar, some friends threw a benefit party for her. A newspaper article on the bash mentioned she’d had to sell some of her hats – she was always known for her lavish hats – just to get food money. Shortly after, she met up with Robert Dougherty, an old writer friend of hers, to write her memoir. By 1965, the project was completed and a publishing deal had been secured. Her half of the advance was $250. “Oh Hell,” she told a friend. “That’ll last about twenty minutes.”

Health problems forced Helen into a series of public hospitals and nursing homes through the late 1960s. Her money was long gone, and the support she’d gotten from friends had dwindled to nearly nothing. She died on May 21, 1969 at the age of 83. The woman who once helped out Al Capone, who made a fortune selling her companionship, and who cursed out bank presidents and sailors alike, had little to show for it all in the end. But as the newspaper eulogies the next day proved, she still had her reputation. An anecdote near the end of her book, after she lost her bar, has her at a train station in Chicago , trying to catch a ride back to Milwaukee . She’s running late and the train has pulled away without her, but the conductor recognizes her as she stands on the platform. He knows the face, the red hair, the figure. He’s been to her place and enjoyed her stories. The man stops the train, and backs it up. “How ya doing, Helen?” He asks her. “Fine, Louie, fine,” she says. “You gettin’ any?” He helps her aboard and directs her to the bar car. The train then chugs back to life and takes her home.

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If you’d like to hear more stories like this one, and want to enjoy an evening boat trip with a full bar, join Matthew J. Prigge for the MONDO MILWAUKEE boat tour this Thursday, June 9th, at 8pm. Tickets are $17.99, available here. Check out the Facebook page here.