K.O. DelMarcelle as Whistling Jack with paramour Lettie (Gina Martino).
Whistling Jack McConnell was one of the toughest gangsters in Philadelphia’s Irish mob in the 1920s. He got his nickname because of his habit of whistling when he was about to turn an enemy’s face into porridge with his tattooed right arm. He variously worked as a stable boy, an ash-cart driver, a professional boxer and was engaged to three women.
But it was a paternity suit was Jack’s undoing. The only way to win in court was to admit the truth.
Whistling Jack McConnell was a girl.
And he. . .she’s the subject of a new play by Villanova grad Andrea Kennedy Hart, “The Toughtest Boy in Philadelphia,” that will make its world premier on June 12 at the Luna Theater, 620 S. 8th Street in Philadelphia, produced by Iron Age Theatre, a Norristown-based theater company.
In the production, Michelle Pauls, who is managing artistic director of B. Someday Productions at Walking Fish Theatre in Kensington, plays a character based on another male impersonator, this one the English music hall actress and singer Vesta Tilley who dazzled audiences on the British stage in drag for more than four decades. In the Iron Age production, her character is known as Tessie Belle. (In real life, Tilley and Jack never met) But that’s not all Pauls does.
“In our production, five women play all the parts,” said Pauls, who is also onstage as Jack’s mother, a traveling entertainer who left her daughter behind for her grandfather to raise.
Whistling Jack was actually born Florence Gray in Ohio. Her gender-bending didn’t start until she moved to Philadelphia with her grandfather. (See a photo of the real Florence/Whistling Jack.)
“From the earliest age, she was the kind of girl who liked to beat up boys and do boy things, and get into a lot of trouble,” says Pauls. “Her grandfather, who was an academic, said, ‘Let’s move out of this small town in Ohio and go to Philadelphia where I can get work and start a new life.’ So that’s what they did. That’s when she became he.”
Her grandfather unwittingly provided Florence/Jack with a nickname that stuck. “He taught her to whistle to befuddle any opponents and Jack would whistle before he beat up street thugs,” says Pauls. “I read in actual newspaper clippings that he used to promote awe in all these other street thugs and mob members by his feats. He even swam the Delaware twice!”
Unlike Jack, her character, Tessie Belle, chose male impersonation as a profession rather than a lifestyle. “She dressed and acted like a man on stage, but sang like a woman and never gave up her womanhood, not like Jack McConnell. She ties all the scenes together, like a spirit guide for Jack. The play is all about artifice and performing. All of us in our daily lives take on many faces and many roles as we go about our business.”
The play also uses this century old true story to explore modern themes of women’s rights, human rights, love and acceptance.
And it’s also a bit of a musical. “I sing three songs that Vesta Tilley sang,” says Paul. “All the actresses also do the sound effects which adds to the vaudeville feel.” (You can hear the original Vesta Tilley sing on youtube.)
In the cast: K.O. DelMarcelle as Jack, with Gina Martino, Susan Giddings, and Colleen Hughes.
The play, which is directed by Iron Age founder John Doyle, will run through June 29. Tickets are $20 and available via ticketleap.
