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Suits Me: The Double Life of Billy Tipton – A Biography of Jazz Era Music That Reads Like a Detective Story

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The jazz pianist Billy Tipton was born in Oklahoma City as Dorothy Tipton, but almost nobody knew the truth until the day he died, in Spokane in 1989. Over a fifty-year performing career, Billy Tipton fooled nearly everyone, including Duke Ellington and Norma Teagarden, five successive wives with whom Billy lived as a man, and three children who he "fathered." As Billy Tipton herself said, "Some people might think I'm a freak or a hermaphrodite. I'm not. I'm a normal person. This has been my choice." This jazz-era biography evokes the rich popular-music history of the Great Depression and reads like a detective story.

326 pages, Paperback

First published May 1, 1998

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About the author

Diane Wood Middlebrook

19 books52 followers
Middlebrook, who taught at Stanford for 35 years, was perhaps best known for Anne Sexton: A Biography. Its intense scrutiny of the poet's life made it "one of the turning points of late 20th-century biography," according to the newspaper. Middlebrook published several other well-received biographies and works of criticism, and was known for funding various arts organizations and literary salons for women. Born in Pocatello, Idaho, she graduated Phi Beta Kappa from the University of Washington in 1961 and earned her Ph.D. from Yale in 1968. She married Carl Djerassi, inventor of the birth-control pill in 1985.

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5 stars
84 (18%)
4 stars
157 (34%)
3 stars
146 (32%)
2 stars
46 (10%)
1 star
21 (4%)
Displaying 1 - 30 of 58 reviews
29 reviews3 followers
May 13, 2013
The author is extremely offensive in her refusal to consider that her subject may not have been "playing a role" or "deceiving" anyone. It is easy enough to imagine a person dressing up as a different gender in order to obtain access to worlds not easily attainable in their present gender presentation. But to live for all of one's adult life in a single gender presentation without revealing the sex assigned at birth to anyone, including your own wife or child, is a strong case for believing that Billy Tipton was a man and the only "double life" was the childhood period in which he was forced to disguise himself as a girl. We can't know Billy Tipton's gender identity for sure. Such things were simply not spoken of back then. But Diane sure as hell could have respected the identity that Mr. Tipton chose to portray.
Profile Image for mr. kate.
41 reviews18 followers
July 9, 2008
This book is totally problematic...as Judith Halberstam discusses in "In a Queer Time and Place". Tipton's life as a jazz musician is interesting and colorful. Middlebrook makes a choice to use both male and female pronouns and flips back and forth between the pronouns and birth name and chosen name like she's writing two characters. She also tends to argue that Tipton lived as man because it was easier to be a jazz musician that way. Middlebrook cannot let gender be complicated, even though she attempts to tell a complicated story When you read this, read it with critical eyes. A prime example of non-trans folks writing about trans folks.
Profile Image for 🫶🏻.
384 reviews119 followers
November 22, 2021
this is bad, transphobic and stupid af. double life? are you joking?

billy tipton did not live a double life. he was not james bond or batman. he was a musician.

billy tipton is incredible but this author is not. she carries this narrative that there was a type of deception within billy tipton's life because he did not advertise the fact that he was trans. read about billy's life elsewhere that does not disregard his gender and suggest that he transitioned to fit in with male musicians.
Profile Image for Melanie.
92 reviews5 followers
August 30, 2014
First off, I didn't read the whole thing. I just couldn't. I had to keep giving myself a quick pep talk before picking it up, telling myself that it had to get better, that the story would pick up, that the author would let go some of her ignorant assumptions and just tell the story. It never got better. I gave up after chapter 9.

The first sentence of the Preface made my blood boil. "This is the story of a woman named Billy Tipton, a jazz musician who lived as a man from the time she was nineteen until 'he' died at age 74 and was discovered to be female." This is wrong on so many levels it's mind boggling. The title itself - "The Double Life of Billy Tipton" - as well as language such as "discovered to be female" is insulting and misleading.

If it were just a question of the author's complete ignorance of trans issues, I might have been able to stomach the book. But the author insists on coming up with all sorts of justifications for Billy Tipton's choices - as if simply identifying as a man wasn't a good enough reason. She continues to refer to Billy as "she", even after he has begun living full time as a man, and despite the fact he spent more than 50 years of his life living as a man.

In addition to all this, I didn't find the writing engaging at all. This book might be more suitable to people interested in the history of jazz in the American midwest in the 1930s and 40s - I felt the author used a lot of historical material to pad the book, because so little is known about Billy Tipton himself.
Profile Image for Chelsea Starr.
73 reviews13 followers
August 29, 2008
i loved this book. but i sort of didn't like how the author offered billy's musicianship and need to fit into a man's world the main reason behind his trans-identity. the cause/effect of that was annoying to me. how about he was trans because he was a man? anyway, besides that i loved the book.
Profile Image for Steph.
5 reviews2 followers
July 19, 2010
The story is incredible but the author is transphobic.
Profile Image for Samantha.
472 reviews17 followers
April 21, 2020
The book is exhaustively researched, and Billy's life was fascinating. I didn't like the pronoun flipping though, and the constant curiosity about why Billy lived as he did, and the way the author framed it as deception or a charade. It's pretty obvious that Billy identified as a man - was a man, and also a musician, and there isn't a whole lot of mystery about it. This book is from 1998, and I wonder if the author would make the same choices if she was writing it today.

I'm giving this three stars for the main subject though.
Profile Image for Brittanclaire.
8 reviews
September 7, 2014
I thought Billy's story was compelling and presented with compassion for the most part. However, I couldn't get on board with the way the author continued to question Billy's motives for his double life, rather than accepting that he identified as male.
Profile Image for Cyd.
568 reviews14 followers
September 14, 2017
An incredible story, both sad and inspiring. The nagging question we are left with is, How much of Billy's choices were due to societal constraints, and how much to self-determination? The interplay between these two forces is the heart of the story.
Profile Image for Janine Southard.
Author 17 books82 followers
Read
September 1, 2025
Gotta get this out of the way: This book was written in the 1990s. So there are gender-related terms that have fallen out of favor and attitudes which have changed with society. This is to be expected when realizing it came out 30 years ago, yes?

Now, the fun bits!

This is the story of Billy Tipton (born Dorothy) who crossdresses in order to get work, at first unconvincingly and then steadily more so until she's living as a man with no one the wiser. Is he a trans man? Is she just in a groove? It's hard to tell based on the evidence presented here, but that's not why you read.

You read it to learn about the jazz scene of the early- to mid- 1900s.
You read it to root for Billy to finally get a job.
You read it to be amazed at how cool all of his (five!) wives were, only some of whom knew their spouse's biological sex.
You read it to appreciate that the other jazz musicians couldn't care less about Billy's sex, even if his friends and family have Opinions with a Capital O.

You read it and wonder at how different life was then, yet is the same now.

Do I want to rate it 3*? 4*? It's fascinating, but sometimes repetitive. And the photo reproductions in the paperback are very low quality.
Profile Image for Hayden.
43 reviews
abandoned
May 31, 2024
dnf’d, but might pick it up another day (when i don’t have a ton of library books to finish). i was willing to look past the author’s misgendering (i’ve never heard of billy being a “crossdresser” as opposed to just being a trans man who only presented as a man, but i gave her the benefit of the doubt — maybe i was wrong) but i can’t look past how boring this book was. also very strange and uncomfortable phrasing in some points.

like i mentioned, i would like to give this book another try even though i have the sneaking suspicion i’ll end up hating it in the end anyway
Profile Image for Jenny.
209 reviews1 follower
August 9, 2010
I was disapppointed that the author of this book could take such an amazing life story and make it boring. The writing itself is problematic - the author uses both he and she pronouns for Billy at different times that I think only make sense to her, and also occasionally inserts herself into the work in first person. I found this jarring and couldn't quite figure out why she did it, since she never actually knew Billy.

The info contained in the book feels thin and padded, which I would like to think is a result of the closeted life Billy led and lack of people living who knew him, but there are actually quite a few of his associates interviewed in the book. These interviews are never incorporated into the narrative very well, though, and I finished the book feeling at arm's length from the subject. Maybe a transgender biographer could better get into Billy's head space and bring him to life?
270 reviews5 followers
October 17, 2025
My wife met the book’s Author at the Book Fair in 2004 and had her sign a paperback copy of her biography of Billy Tipton. Now, who, you might ask, is Billy Tipton? He lived his whole life so as not to give away his personal secret. It was that his real name was Dorothy Tipton. Yes, she kept her gender secret from the age of 19, through five marriages, from her fellow musicians. And he also adopted three sons in 1961 with one of his wives, Kelly. Dorothy/Billy died at the age of 75 in 1989 (born 1914). He first began to appear as a man in 1933. When his real sex was discovered during the autopsy, the press got hold of the death certificate and the story became a national phenomenon.
Dorothy/Billy died at the age of 84 in 1989 (born 1914). He first began to appear as a man in 1933. When he found bands willing to hire him/her (both dance and radio), they did not hire female members. He was a very good Drummer and Sacs player. Billy began to get jobs, and he soon became a well-known Band Leader and worked as a talent agent. He recorded 2 Jazz albums in the 1950s.
The Author says Dorothy wanted to become a Man and worked on it every day. Billy saw himself as an Entertainer. When he found bands (both dance and radio) did not hire female members. He was a very good Drummer and Sacs player. Billy began to get jobs, and he became a well-known Band Leader and worked as a talent agent. And recorded 2 Jazz albums in the 1950s.
The Author says Dorothy wanted to become a Man and worked on it every day. He saw himself as an Entertainer. To a degree, Billy’s story had me rethinking my perceptions of reality, which depend on what I see to be true. I told friends that I found the book very interesting. Especially when I tell them what the book is about, they often laugh and say, “No way, I would know.”
Profile Image for Allison Roy.
392 reviews
July 25, 2019
This book I have forever planned in reading “next” after I finished anything else, but I always grabbed another book. This has been going on for probably close to a decade. Finally picked it up! My opinion is that nonfiction is always a bit better than fiction because I mean, it happened! It’s interesting enough to put down on paper!

From this, I expected something more shocking I suppose? This is about Billy Tipton, a musician who was born a woman but became a man which helped her become successful with her passion, which was jazz music. It seems like Billy didn’t actually fool a bunch of people, but the attitude at the time was really to just mind your own damn business. Billy was a good person so it seems everyone just left it that.

There are pictures provided throughout where I just have a hard time thinking Billy hid her sex from anyone but who knows, I guess the way people carry themselves is what matters. I am terrible with names and there were SO many musicians name dropped in this I could not keep up.

I felt like the book ended rather...suddenly and sadly? Billy never wanted to become TOO famous because she didn’t want the exposure of being called out, wouldn’t accept social security near the end so he struggled so again no one would find out he was physically a woman. Also, dude had SO many wives AND THEY DIDNT KNOW. PUH-LEASE. They touched base on that but I just need to know more on that. Anyways, okay read. Sorry for the nonsensical review.
This entire review has been hidden because of spoilers.
Profile Image for Kelli Johnson.
172 reviews
December 10, 2022
I struggle a bit to review this book. There were things that were problematic and I can see why others were critical. Great research, but a bit dry. I think the book could have been more exciting...but this was a truly riveting story.

In a time when a female was not able to have the same opportunities as men, or be taken seriously in a number of careers, situations, this person created her own life. The way Billy was able to live the life he chose with partner, children, collaborators ....specifically in that time period...was so interesting! I can't imagine how challenging life must have been.

I originally read this book because I am from Spokane, WA....but I was fascinated with this individual and I hope that he found some joy or peace in the life he wanted to live. I felt this story needed to be told and I don't believe the author was trying to be disrespectful. I think she was also fascinated.
137 reviews4 followers
December 17, 2021
I really loved and was moved by the documentary on Billy Tipton (No Ordinary Man), and picked up this book partially because a friend was so excited about reading it and delving more into his history.

It's rather jarring to read this book written in the 90s about a trans man (or at the very least, genderqueer person), as it was a very different time then... but I was pretty impressed with amount of research Middlebrook did to bring Billy's story to life. You kind of have to get past all of the talk focusing on Billy's "act" to appreciate what an interesting life Billy lived, and admire him as a musician, performer, and person in a lot of ways, though Middlebrook is also truthful about the ways in which Billy's agreeableness ended up not serving him (or his children) in the end. What a life, Billy. Hats off to you.
115 reviews1 follower
March 30, 2024
Louise Erdrich mentions this book at the end of The Last Report on the Miracles at Little No Horse. Author Middlebrook speculates in places [due to a lack of evidence], but does it well. As I read this book, I thought of a quote attributed to Mark Twain: "Truth is stranger than fiction..." It's sad to think that Billy Tipton felt compelled to lead the life she/he led. And sad to think that even now, many still treat women as "lesser" than men. Worth reading.
Profile Image for William.
116 reviews11 followers
January 26, 2022
Unfortunate that the only book written about the life of a great trans man is written by someone aimed at proving he was "an actor" in his everyday life. Great, overlooking the contemporary to its day idea of what trans is, and how he supposedly did this as a true entertainer putting on a lifelong show, and not just a trans person. But I'm glad at least some record of him exists.
Profile Image for gnarlyhiker.
371 reviews16 followers
May 30, 2023
yes, too bad middlebrow didn't believe billy was who he said he was and lived his life the way he lived. other than this blatant disregard towards billy, the research and grasp of the time period makes for a good read

good luck
Profile Image for Sheri Lutz.
73 reviews2 followers
July 5, 2019
Given that it was written in 1998, *21* YEARS AGO, the language is dated. However, it's scrupulously researched and thoughtful.
Profile Image for Saturn.
12 reviews
August 3, 2019
In spite of my interest in Billy Tipton, this was absolutely unbearable to read. The constant switching of pronouns was jarring to say the least, and the whole thing felt bordering on transphobia
8 reviews
July 2, 2021
Important novel bringing trans history to the forefront by offering a snapshot of Tipton's life.
Profile Image for Barbara Clifford.
274 reviews2 followers
January 12, 2023
This book was fascinating how the charade could be kept so secret but I have to give him credit he lived the life he wanted to back when it could have cost him a lot. He was brave.
Profile Image for Ursula.
276 reviews38 followers
August 8, 2011
This was a very interesting book about Billy Tipton, a musician in the jazz/swing era who was born a woman but passed as a man almost his entire adult life. It's both fascinating and frustrating trying to dig into how that was possible, and who knew what and when, because he didn't confide in anyone at all.

Nevertheless, the fact that Dorothy Tipton (as Billy was named at birth) started dressing as a man to pursue a career as a musician was definitely known in her home state of Oklahoma and surrounding areas when she started out. As much as a modern reader would expect people in the early part of the 20th century (and in that part of the country) to be up in arms about her cross-dressing, or expose her ruse at any chance, they didn't. Billy was part of the entertainment world, and "show people" had different rules that the average person didn't always understand, but also didn't infringe upon. As Billy found more success as a musician and began moving farther and farther from home, years passed where no one knew his secret. Slowly it became something he really had to take steps to keep hidden, lest he lose everything.

Billy lived with 5 different women over the course of his life, calling them all his wives even though they were never legally married. The women the author spoke to claimed they didn't know Billy's secret, nor did they notice anything amiss in their relationships with him. The truth was revealed when he died, but with very few exceptions, the revelation didn't change how anyone he knew viewed him - he was still remembered as the man they had known, in spite of being physically female.
Profile Image for Andreana Sutherland.
11 reviews20 followers
July 20, 2021
The book mainly traces Billy Tiptons life & career as a musician. It is an average biography, I felt a little let down by it, but I am pleased to now know the name Billy Tipton. Makes me wonder how many more women lived their lives successfully as men in the past without raising the slightest suspicion. ? We do not know why s/he chose to live this way, though, so I feel more could have been made of that question. Was he transsexual? Was she a lesbian? Or was it just that women could not have successful careers due to sexism back in those days? The book doesn't answer or contemplate these aspects, as I remember, it just traces the life of Billy Tipton the jazz musician.
I find the title "The Double Life of..." to be misleading, as he didn't live a double life, he lived one life; that of Billy Tipton, jazz musician. Just because his sex was discovered to be different upon his death, does not mean he lived a double life - there was no other, hidden life, it is just the biography of a jazz musician who happened to hide his real, biological sex. For what reason, the book does not make clear.
Could be better, at least in my eyes. I must give it another go, try reading it again, problem is that my main memory from reading it first time around was a feeling of tedium, so it doesn't reach high on my 'to read again' list!
Profile Image for Katina.
540 reviews8 followers
March 16, 2008
Diane Middlebrook is a great biographer. Sadly, I found out about her because I stumbled across her obituary on Stanford's webpage several months ago. RIP.

The story of Billy Tipton as she wrote it is very compelling. I'm quite sure the truth about Billy being Dorothy first made news in the tabloids. True to form, when I told people about the book I was reading, their first questions all revolved around sex. While the book does answer some of those questions, it is an in-depth exploration of gender, sexual orientation, transgender issues, passing, drag, and even touches on intersex issues. I definitely enjoyed this and would highly recommend. WTTW, however, it focused more on old-timey jazz than I would have preferred and got slow at times.
Profile Image for Martha.
14 reviews1 follower
April 12, 2012
I found this book fascinating, although sometimes frustrating. Middlebrook attempts to delve into Billy's reasons for "passing" without any evidence, really, except for what other people in Billy's life felt to be the cause and the cultural climate. Ultimately, it felt a bit cobbled-together--part musical biography and part gender journey. I also found Middlebrook's use of pronouns confusing, in spite of her explanation in the forward. It did not seem consistent to me, and sometimes felt denigrating of Billy's choices. Ultimately, I found this to be inspiring, in spite of these drawbacks--Bully did what Billy did, and the hows and why were no one else's business. Billy lived life on Billy's terms and was accepted by colleagues, friends, and partners. That's a heck of an achievement.
Profile Image for Liesl.
61 reviews
August 30, 2015
Billy Tipton's is a fascinating story with a key hole--Billy was never fully open with anyone about how he viewed himself. To family who knew that he was born and raised as a girl, he was "passing as a man" in order to make a career in the early and mid 20th century. To the women who thought themselves his wives, he was a private but loving husband.

While Billy surely did tell lies to live as he did, Middlebrook's perspective seems to see him as a deeply unknowable liar. It seems that the ideas of Billy's time have overtaken real thoughtfulness about the situation. She is dismissive of the idea that he was transgender, focusing instead on the belief that he was more of a deceitful lesbian.
This entire review has been hidden because of spoilers.
Profile Image for Gina.
22 reviews5 followers
January 12, 2011
Although Billy left no notes or diaries about his life or the choices he made, Diane Middlebrook does a fairly good job of recounting the choices that took Dorothy and made her into Billy Tipton; jazz legend. If you have the oppotunity, search out Billy's music; its amazing. The story is sad and unfortunately holey in places. Was Billy a lesbian? Was Billy a Transman? We will likely never know. There is some triggering language in the book due to the interviews of people in Billy's life being from a time when "invert" was the correct term to use for persons of different sexual orientation and/or gender identity.
This entire review has been hidden because of spoilers.
Displaying 1 - 30 of 58 reviews

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