Playing the part is never a simple or straightforward process for Nellie McKay. A singer-songwriter and pianist with a gift for wily provocation, she knows how to disappear into character with a song. And she pushes that impulse further with A Girl Named Bill: The Life and Times of Billy Tipton, the cabaret show she’s presenting Thursday through Saturday at 54 Below.
The show is inspired by a fraught and fascinating piece of jazz history. Billy Tipton was a fine journeyman pianist whose career stretched from the 1930s to the ‘70s, mainly in and around Spokane, Wash. It was only when Tipton died in 1989, at 74, that those closest to him discovered he had been assigned the female sex at birth.
Tipton’s story has been a source of intrigue ever since, not only in the field of transgender studies but also in popular culture. He has inspired short stories, plays and songs, a novel, even an opera. A biography — Suits Me: The Double Life of Billy Tipton, by Diane Middlebrook — was published in 1998.
McKay’s contribution to this story is an idiosyncratic cabaret revue that explores precarious emotional territory under the cover of show-business panache. In addition to singing, she plays piano and ukulele in the show. She also plays Tipton, pointedly, as both a man and a woman.
The implied contrast between glossy surface and churning undercurrent has precedent in McKay’s musical history: it was one subtext of Normal As Blueberry Pie, her excellent 2009 tribute to Doris Day. A similar tension animates many of her own songs, which bristle with originality even when they borrow a page from trickster tunesmiths like Bob Dorough. When she played a Tiny Desk Concert in 2011, her set list included a playful but pointed lite-reggae tune, “Caribbean Time.” Her newest track, “Ridiculous,” is a folk-rockish protest song with a typically deadpan air. (Activist expression has always been important to McKay, who often speaks out on behalf of feminist and civil rights causes, and is a prominent ally of People for the Ethical Treatment of Animals.)
A Girl Named Bill premiered at 54 Below in 2014, to enthusiastic reviews. Writing in the New York Times, Ben Ratliff hailed the show’s original run as one of the best things he saw that year: “Under deceptively ragged humor and a wildly broad repertory illuminating various angles of the story — by Jelly Roll Morton, Yoko Ono, Cindy Walker and Ms. McKay herself — lay a devastating theme: how, and why, to live with secrets.”