Jaimie Sherling spent the first seven years of her life in Queens, New York. The baby of the family—at that time—Jaimie relied on her older siblings to speak for her. Even as a toddler, she understood the power of efficiency. With a two-word vocabulary for years, no one would have predicted that one day this quiet child would be told she talked too much—and would even write a book.

One of eight children, Jaimie grew up a people pleaser, a perfectionist, and a problem solver. Jaimie spent her formative years in Florida, upstate New York, and Wisconsin, where she graduated from UW-Madison. After graduation, she moved to the San Francisco Bay area. Two years later, she was drawn back to Madison where she still resides today. Go Badgers!

Throughout late elementary and middle school, Jaimie was told that she talked too much. In 2017, Jaimie put that mouth to good use. She performed with Sun Prairie Civic Theater, where she was part of the company in both The Wizard of Oz and Joseph and the Amazing Technicolor Dreamcoat. Through that experience, she became friends with her first drag queen, Beverly Bee. Beverly introduced Jaimie to live local drag at FIVE Nightclub. This glorious experience had such an impact, she quickly became an almost nightly regular.

In 2018, Jaimie’s life turned upside-down. Five months before her 42nd birthday, Jaimie was diagnosed with breast cancer. After recovering from a double mastectomy, Jaimie felt frustrated by the way her clothes fit her new, post-surgery body. Through many discussions in online support communities, she found she was not alone. Armed with the desire to solve a problem, Jaimie worked with a local pattern maker to design a unique clothing line for her sister survivors.

Jaimie was ready to launch it in spring 2020. Unfortunately, the pandemic had other plans. With most of the world in pajamas and yoga pants, Jaimie made the difficult decision to delay the launch. With too much time on her hands and no one to talk to (in person), Jaimie poured her energy into writing a memoir. From Queens to QUEENS: How the Madison Drag Community Saved My Life was published in September, 2021. These days you can still find Jaimie living in Madison, where she keeps busy hosting brunch, glamming out on #FormalFridays, and attending shows at FIVE on a regular basis.

2022 Great Madison LGBTQ+ Artist Survey

Michael Darling, Musician
Jaimie Sherling, Author/Designer
Will Kiley Santino, Visual Arts / Illustration