book reviews

Repost: Suits Me: The Double Life of Billy Tipton

I originally posted this review on on March 4, 2012. It’s being reposted as/is.

A couple of months ago, I happened to see a Dr. Phil rerun about three adopted brothers who were estranged because the youngest brother had screwed the two older brothers out of an inheritance.  At first, I didn’t pay a whole lot of attention.  The subject matter seemed to be very typical for a Dr. Phil show and I generally find Dr. Phil and his ilk annoying.  But after the brothers started to elaborate on their story, I sat up and took notice.  It turned out this particular episode of Dr. Phil was about much more than just squabbling siblings and inheritance money. 

These three men were the adopted sons of jazz musician Billy Tipton and his “wife” Kitty, a former stripper.  Kitty Tipton was one of several women who had married Billy Tipton, who was a moderately successful entertainer in the first half of the 20th century.  By most accounts, Billy Tipton appeared to be a somewhat short but entirely heterosexual man.  What almost no one knew until the day of Billy’s death in Spokane, Washington on January 21, 1989, was that Billy Tipton was actually a woman! 

Though I was around in the 1980s, somehow I missed all the talk show hype about this case that came out after Billy’s death.  I was just hearing about the case for the first time as I watched that episode of Dr. Phil.  I immediately went to to see if anyone had written a book about Billy Tipton.  Indeed, in 1998, Diane Wood Middlebrook published Suits Me: The Double Life of Billy Tipton.  I’ve spent the last couple of weeks reading about Billy Tipton’s remarkable life and death through reading Middlebrook’s very thorough and well-written book.

Why she became he…

Born in Oklahoma City in 1921, Dorothy Lucille Tipton grew up Kansas City, Missouri.  Dorothy’s parents had split up, so she was raised by an aunt who insisted that she learn how to play the piano. Dorothy turned out to be very musically talented.  She could sing, play saxophone, and play the piano.  She was also a very capable bandleader and entertainer.  Unfortunately, at the time Dorothy was coming along, women were not commonly accepted as jazz musicians. 

At age 19, Dorothy initially started dressing as a man so she could play the kind of music she wanted to play.  Noting that movie star Joan Crawford’s real name was Lucille and people had called her “Billie” as a nickname, Dorothy was inspired to use her middle name Lucille as the basis for changing her name to “Billy”.  At first, some of her fellow musicians knew that she was just dressing in uniform so she could play jazz with them. 

As time went on, Dorothy’s original gender identity went by the wayside and she lived as a man 24/7.  She totally passed as a man, mainly because she was careful never to let anyone see her naked, and dazzled her paramours by being suave and debonair.  The different women who had relationships with Billy over the years somehow instinctively understood that Billy treasured his privacy and knew that they weren’t to touch him or barge in on him when he was in the bathroom.  Indeed, Middlebook reports that “Billy Tipton” was so convincing that even his several “wives” never knew the secret after their unofficial unions were consummated.  They were all shocked when the truth came out after Billy’s death because they had all had sex with him.  Naturally, the lights were always off.  One woman even called Billy “the love of her life”.

My thoughts

This book is absolutely fascinating.  Diane Wood Middlebrook does a great job writing Billy Tipton’s story and explaining all the angles of Tipton’s life.  Her writing is very readable and conversational.  I had no trouble falling into this book and getting engrossed in Billy Tipton’s amazing story.  Middlebrook also includes pictures, which I think are essential to this particular book.  Every time I ran across photos, I stopped and studied them just to examine how the people in Billy’s life were fooled.  Personally, I think Billy looked quite feminine, but I guess I can see how people fifty or sixty years ago would just take his word for it that he was a man.  People didn’t talk about such personal things back then as much as they do now… or so my mother often scolds me!

I will warn that there are a few topless photos in this book.  They aren’t of Billy Tipton, though, who never let anyone see his chest, which he had bound with bandages.  Tipton explained the bandages were there because he’d had injuries from an accident that had never healed properly.  As I look down at my own D sized breasts, I couldn’t help but wonder about how Billy handled the more personal aspects of being a female… like menstrual periods!  How on earth did Billy sustain marriages to other women and keep his periods a secret?  This is just one of many questions I pondered as I read this incredible true story.


Sometimes you really can fool all of the people all of the time.  This is a fascinating book for music buffs, show biz mavens, psychology fans, and people who just love outrageous stories.  I happen to fall into all four categories.  If you do too, I definitely recommend reading Diane Wood Middlebrook’s book, Suits Me: The Double Life of Billy Tipton.

A video about Billy Tipton.

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