Suits Me: The Double Life of Billy Tipton

In the Billy Tipton biography "Suits Me," there's a picture of the little-known pianist standing next to Duke Ellington. Snapped in an Albany, Ore., nightclub in 1954, the photo is as close to jazz fame as Tipton ever reached.

While he reportedly played decent swing-style piano in the manner of his idol Teddy Wilson, and even recorded a couple of now long-out-of-print LPs, Tipton never made much of an impact on popular culture until his death in January 1989. That's when it was discovered Billy wasn't a he at all, but a she.

Dorothy Lucille Tipton, born in Oklahoma City in 1914, assumed the identity of a man in 1933 and kept up the act until she died, letting very few people in on the secret. Not even the five women who called themselves "Mrs. Tipton" (there never was an official marriage on the books) nor his three adopted sons knew.

After you get over the initial "wow!" you're left with a big "why?" Not to mention "how?"

"Suits Me" explains quite a bit about how Tipton was able to pull it off (bandages to hold in her breasts, a prosthesis in the pants, a naturally low voice, and lovers who were relatively naive. Plus, the bedroom lights were always off and the bathroom door always closed). But his/her motive remains a mystery.

Since Tipton never got around to explaining herself, Middlebrook and the Tipton family members and acquaintances interviewed in the book can only speculate. And that's what the book does, sometimes to the point of absurdity. "Why on earth did she do it?," Middlebrook writes. "Too bad ... Billy did not write a memoir or leave a letter marked with the instruction 'To be opened after my death.' We will have to substitute imagination for the absent documentation. Perhaps what happened went something like this."

Middlebrook uses Tipton's story as an excuse to indulge her own musings on the nature of gender and sexuality in a post-Michael Jackson, post-Madonna world (she even goes so far as to reference RuPaul). As much as she aims for postmodern profundity, it all comes off as pretty pedestrian.

Perhaps Tipton masqueraded as a male because it was tough for women to break into jazz. Once she assumed the role she had to keep it up. Or perhaps cross-dressing was a reflection of her sexuality. Middlebrook keeps posing the same questions for 280 pages, never reaching a conclusion.

So hard up to capture any sense of Tipton's private thoughts or true personality, Middlebrook even speculates how certain books or films might have influenced Tipton, had she read or seen them, which we'll never know if she did. "The year before Billy started cross-dressing, MGM released Queen Christina in which Greta Garbo wears male attire to express her authority as sovereign and 'to be free,'" Middlebrook writes. "...Think of Billy watching Garbo act out the solution to the problem of being female in a role reserved for males, before her very eyes!" Or better yet, think of Middlebrook watching Queen Christina and musing about how sharp and insightful readers and critics will think she is for mentioning the film in relation to Tipton. It's one of many silly non-points in the book.

Where Middlebrook succeeds is in capturing the sense of what it must have been like to be a traveling musician in the post-big band, pre-rock'n'roll era of the late 1940s and early 50s, when Tipton and her groups toured first the Oklahoma-Kansas-Texas region and later a circuit that took in portions of Montana-Idaho-Oregon and Washington State. Tipton ultimately settled in Spokane.

The musicians played a few small band swing tunes, but in order to make a living had to play mostly pop songs and standards, adding corny one-liners and Vaudeville-type skits to the mix. Though she occasionally crossed paths with greats such as Ellington while on the road, Tipton couldn't really be considered a jazz musician.

But she was an incredible improviser. Her lifelong act was likely more daring, more original than anything she played on the piano. Tipton's life is a fascinating unsolved mystery story. Perhaps another biographer will do a better job telling it in the future, though it's unlikely they'll get any closer to solving the puzzle.

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