June 17, 2024 | Will Eikenbary

Shannon Dupree: breaking barriers to be seen

She was told to "stay in her lane." Instead, she chose to break all the rules -- and became a drag legend.
Photo: Devin Antheus and Harry James Hanson

Shannon Dupree is a name synonymous with entertainment and resilience in Milwaukee's vibrant drag community.  Known for her dynamic performances and unwavering spirit, Shannon defies labels and embraces a fluid identity.  

She prefers the title "entertainer,"  distancing herself from the conventional term "drag queen." For nearly 13 years, Shannon has been captivating audiences at Hamburger Mary's, where her presence lights up the stage every 2nd, 4th, and 5th Saturday of each month.

Shannon’s journey into the queer community began in the lively days of Club 219. Initially, she was unimpressed by the performances she saw. Boldly, she voiced her dissatisfaction, prompting a challenge from another performer: "If you think you can do better, then try it yourself."

Rising to the occasion, Shannon had a girlfriend help paint her face for a contest, and her debut performance was met with victory. This triumph ignited a passion that would steer her career for decades to come.

Mentorship has played a crucial role in Shannon’s development as an entertainer. She speaks fondly of Tasha Long, a queen whose talent and dedication left a lasting impression.

"Longevity is a queen," Shannon says, admiring Tasha’s inspiring journey and her significant contributions to the drag scene.

Shannon’s favorite memories are steeped in the joy of performance.

"It was fun," she says, recalling the applause and adoration from the audience creating an atmosphere of love and acceptance. This sense of community is what drives her to continue performing, always aiming to bring a smile to her audience’s faces.

Pride in her achievements is a hallmark of Shannon’s narrative. She has won numerous titles, defying expectations and breaking barriers. "I won big girl, small girl, old girl," she declares, embodying the spirit of inclusivity and talent. Shannon’s goal is simple yet profound: to make drag fun and accessible for all.

However, Shannon is not without concerns about the future of LGBTQ life in Wisconsin. She speaks candidly about the challenges she faced as a “big black girl” in the drag scene, often told to stay in her lane and only participate in plus-size pageants. Despite proving her worth time and again, these prejudices persist, and Shannon hopes for a future where talent is recognized regardless of size or color.

shannondupree Shannon Dupree at Hamburger Mary's
shannondupree Shannon Dupree

To the next generation of LGBTQ individuals, Shannon offers advice she’s learned over the course of her life: "Look, listen, and learn." She encourages young people to observe their surroundings, listen to those with experience, and absorb wisdom from various sources. "You can take a nugget from anyone and make it your own," she advises, highlighting the importance of mentorship and community support.

In addition to her work at Hamburger Mary’s, Shannon finds solace and family at Fluid Bar, her second home. The camaraderie and support she finds there reinforce her belief in the power of community. Her performances at these venues are more than just shows; they are celebrations of life, joy, and resilience.

Shannon Dupree's story is a testament to the power of perseverance, talent, and authenticity. Her journey from Club 219 to the stages of Hamburger Mary's and beyond showcases the impact of embracing one's true self and the importance of creating inclusive spaces.

As she continues to entertain and inspire, Shannon remains a beacon of hope and joy in Milwaukee’s LGBTQ community.
hamburgermarys Photo: Mark Mariucci

The concept for this web site was envisioned by Don Schwamb in 2003. Over the next 15 years, he was the sole researcher, programmer and primary contributor.

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The concept for this web site was envisioned by Don Schwamb in 2003, and over the next 15 years, he was the sole researcher, programmer and primary contributor, bearing all costs for hosting the web site personally.