Nellie McKay

A Musician Named Nellie

British-American musician Nellie McKay tends to find the inspiration for her musical projects and performances in other people, and most of her subjects, although not widely known, are extremely interesting.

Among other projects, McKay has written and performed musical biographies about Barbara Graham, the third woman executed at San Quentin prison, and Rachel Carson, a marine biologist and environmental pioneer.

“Other people’s problems are easier than your own,” McKay laughs. “It’s lovely trying to recognize what’s in somebody else’s heart and soul, or try to.” 

She adds: “People are so complicated; they’re cauldrons of contradictory things.”

And when she was taking on the role of Billy Tipton, a transgender 1940s pianist and bandleader, for her current musical biography, she fully submerged herself into the depths of that contradictory cauldron. Tipton’s story first blipped on McKay’s radar when her mother found a used book about the midcentury transgender musician in a thrift store. 

Tipton’s story goes like this, McKay recaps: “Billy Tipton was born Dorothy Tipton.” At first, Tipton dressed as a man only for his performances, but as time went on, he began to live his life as a man on and off stage. 

“Billy spent quite a lot of time in the Northwest. He came from middle America, Oklahoma and Missouri,” McKay says. “He wanted to travel more, but he was too afraid that he’d be outed in the big cities, so the Pacific Northwest was a good compromise between urbanity.” 

Tipton had various female love interests, says McKay, tallying a total of five wives throughout the span of his life. In order to hide his identity, he told his lovers he was injured in an accident as an excuse for why he kept his chest bound and genitals hidden, McKay says.

Tipton continued playing music into the 1970s, until arthritis and other health problems hindered his ability to perform. He died in 1989. It was not until his autopsy that it was revealed he was anatomically female.

McKay has been performing the show based on Tipton’s life, titled “A Girl Named Bill,” off-and-on since 2014. In the show, McKay and her backing band perform a mix of jazz and cabaret originals as well as “a potpourri of different sounds from different eras” to reflect events in Tipton’s lifespan, McKay says. 

During the show, McKay dresses in drag in an attempt to resemble Tipton, sporting short hair and a loose-cut suit while she performs. When researching the bandleader, she tried to step into his shoes, and mindset, as much as she could.

“It’s so hard to imagine how he did it,” McKay says. She says she experimented with attempting to wear a binder around her chest and a male prosthetic between her legs. “I couldn’t do it,” says McKay. “I lasted about two hours.”

Other than dressing the part, McKay says her transformation into Tipton for the stage was not that much of a challenge. “Besides trying to practice for once,” McKay laughs, “I kind of act not particularly like a lady anyway.”

Though McKay is known for her quirky, catchy songwriting, she is also a vocal feminist and civil rights activist, making her portrayal of Tipton more than just a musical performance.

McKay says she also learned a lot from Tipton personally when researching him. “Billy, he was very soothing. He was gentle and friendly and kind, and those are qualities I would like to work on myself,” she says. 

Regardless of the controversy surrounding his gender expression, Tipton’s dedication to his art and to living life as his true self is an undertaking everyone should want to aspire to. — Meerah Powell

Nellie McKay is performing A Girl Named Bill: The Life and Times of Billy Tipton at 7:30pm on Saturday, July 1, at The Shedd. Tickets range from $28-$36 with additional discount opportunities available. Visit for more information and to purchase tickets.

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