Queen of the Deuce is a must-see documentary that shares the remarkable story of Chelly Wilson, a tenacious Jewish Greek-born woman who evaded the Nazis, arrived in America in 1939, and became a legendary figure in New York City as a pioneer of porn cinema. From the late ’60s to the mid ’80s, Chelly owned and operated multiple theatres in and around 42nd Street, the notoriously seedy strip known as The Deuce.

Filmmaker Valerie Kontakos was a teenager when she was first introduced to Chelly. “I started selling tickets in the Tivoli Theatre on Sundays, when they would show Greek films. The rest of the week it was all porn,” says Kontakos, who was instantly struck by Chelly’s larger-than-life personality. “She was everything I wanted to be when I was fifteen years old: strong, independent, self confident, a decision maker. Those were all qualities in a woman that I really looked up to.”

Valerie has thought about making a documentary about Chelly for many decades, but admits that it was only in recent years that she felt ready to tell her story. “I had to mature enough to be able to make the film, to be able to handle all the grey areas in her personality. There’s a lot of black and white, but there’s a tremendous amount of grey stuff in between, and I don’t think I could have handled it earlier.”

Chelly moved in many circles, and played poker late into the night with well-known mobsters. She was a shrewd businesswoman, who was empathetic but tough. Her eclectic apartment sat on top of one of her bustling theatres, secured with multiple locks. Inside, rooms with mismatched furniture were full of raucous gatherings, plumes of cigarette smoke, and shoeboxes crammed full of money. Chelly wasn’t always likeable, but she was undeniably impressive, and she made a big impression on young Valerie. “It’s a portrait that does her honour… It’s not all complimentary.”

Queen of the Deuce is a riveting portrait of Chelly’s big complicated life, but it’s also a story about the transformation of a city. “It’s become sterilized. It’s become much more corporate. It’s lost its edge,” says Valerie, describing New York today, as compared to the city she grew up in. “It was exciting. You’d get this sense of adrenaline, like you were walking through a combat zone. It was very active. There were lots of things happening all the time, whether it be from drugs to stolen goods being sold to pimps and prostitutes, there was so much going on in the streets, and you just kind of had the opportunity to walk through it, rather than see it on a screen or read about it.”

The doc uses a mix of archival footage, interviews, family camcorder videos, and animation to flesh out Chelly’s story.  It’s captivating from start to finish, the kind of doc that leaves your jaw hanging, and inspires dozens of conversations, be it about WWII, the American dream, queer culture, urban development, porn, or the excruciatingly tough choices we make to protect our loved ones.

Audiences will be inspired by Chelly’s exceptional foresight, her ability to take risks, absolute uniqueness, and chutzpah. “Everything fascinated me. I hope everyone enjoys it, as much as I enjoyed making it.”

Queen of the Deuce screens for one-night-only in Toronto, Saturday June 3, at the Hot Docs Cinema, as part of the Toronto Jewish Film Festival. Don’t miss this unforgettable gem. The doc will have its broadcast premiere on Saturday, June 24 on CBC Docs.