Diane Wood Middlebrook, author of Suits Me: The Double Life of Billy Tipton

August 29th, 2000

Diane Wood Middlebrook,

author of

Suits Me

The Double Life of Billy Tipton


Biographer Diane Wood Middlebrook’s Suits Me tells the story of a brilliant deceiver who lived and loved in two skins, one of each sex.  Jazz musician Billy Tipton grew up as Dorothy Tipton but lived as a man from the time she was nineteen until she died at the age of seventy-four.  Tipton’s death made news all over the world, not because he was celebrated as a musician but because of the scale of his deception – he had been married to five women and had reared several adopted children.

Ms. Middlebrook, one of our most brilliant biographers, shares her thoughts on this remarkable biography in our exclusive Jerry Jazz Musician interview.  Interview hosted by Jerry Jazz Musician publisher Joe Maita.





Billy Tipton


JJM I am very intrigued by your career path. You wrote a book on the poet Anne Sexton, and you are currently writing a book on the English poet Ted Hughes…Was there a particular biography that you read as a child that made you want to be a biographer?

DWM I hadn’t thought of writing biographies – the answer is no. I was invited to write the biography of Anne Sexton after I had written a small article about her. The editor who was helping her estate find a biographer read it and indicated that he liked the way I wrote about her and thought that I might be able to write for a general audience. That was the first time it ever occurred to me that I might do a book like this. I had gotten very interested in women’s careers, and I thought that Anne Sexton’s career was an interesting story, to say the least- the improbable development of a woman who had no education and a major mental illness, and you wonder “how did she do it?” So, I sort of backed into it. While I was working on Anne Sexton, I got tremendously interested in biographies in general. I think it’s a wonderful way to read and write history.

JJM The world is your oyster…there are so many people you can write about.

DWM And they take you place you could never go. It’s a great way of life for me, and it’s a particular way of writing that I like very much.

JJM Who was your childhood hero?

DWM Wonderwoman!

JJM No!…Why was Wonderwoman your hero?

DWM I think because I was really smitten by the idea of goddesses and gods. I used to have one of those childhood fantasies where I was really a goddess. My mother named me very fancifully – my middle name is Helen, my first name is Diane. She was thinking of the moon goddess. I was a first child too, so I was an indulged, contented child with a certain sense of entitlement, so I used to have this fantasy that I was actually a goddess. Wonderwoman came about as close as they got. I used to buy those thick Wonderwoman comic books…

JJM You grew up in Spokane, Washington, where Billy Tipton lived the last part of his life. Do you or your folks have any memories of Billy Tipton? Were they able to help you during the course of the book in terms of remembering Tipton?

DWM People in Spokane remember Billy very well, including my father, but just as a professional. He was very well known because he was one of those people who was really an entertainer. Nightclubs really made use of musicians to get people to drink. Certainly there was a dress-up side of dancing and glamour, but the people would really love the night club act he developed, as well as being quite a good musician. So, he had lots of work. At the time my parents were going out dancing in Spokane he was actually a booking agent and he didn’t have a steady gig at a nightclub. He would fill in and occasionally play gigs himself, and when he did, people would always come to see him because he was well known. When he died, people were absolutely dumbfounded to discover he was a she…

JJM What amazes me about the book is the deception he played, and his ability to surround himself with people who he could manipulate in some way, including himself, because, after all, he died of an ulcer. I’m sure a lot of that was because of him worrying about being discovered…

DWM I think that’s probably correct.

JJM What drove you to actually pursue this subject for a biography?

DWM I encountered Billy’s obituary in the New York Times in February, 1989. I saw this story over coffee that had a dateline of Spokane, Washington. I looked at it, read the story, and was absolutely struck with disbelief! The story itself was very compelling..it had a kind of touching quality to it. The obituary told the story of a man named Billy Tipton, who at the time of his death it was discovered that he had a woman’s body. His wife and his two sons were among those that didn’t know that Billy was female. One of the sons is widely quoted as saying, “Well, he will always be Dad to me.” Right away, there is the voyeuristic fascination with how can someone not be known by a wife and sons to be the wrong sex? Then, it hit me that the story itself is a very ordinary story, that we are connected by relationships, and our relationships are projected on to who we think they are. So when the son said to me “He will always be Dad to me” it didn’t matter whether it was a female person, and I thought right away that, yes, that’s correct – “Father” is a relationship, it’s not a sex.

JJM That’s the beauty to the story…There’s a lot of sadness to the story too, frankly…

DWM Yes, but on the whole it isn’t a sad story. Let’s go back to the other part of the story for a second…the children were adopted, and the wife claimed that she never had sex with Billy, which as we find out in our culture is not altogether that impossible to imagine. We have totally conventional notions of what all these roles mean, and you understand there are lots and lots of differences in people, and lots of ways to constellate relationships, partnerships, and all kinds of things. If you begin immediately to say each of the things being talked about is a role, whether it be age or sex, its all performance…That, of course, is what my book is about.

JJM A major theme of the book is the frustration that female musicians had in getting recognition and being taken seriously…Before he was Billy Tipton, she was Dorothy Tipton. She was sexually attracted to women, but socially attracted to work normally reserved for men. What was the most influential event in Dorothy’s youth that may have attracted her to these roles normally reserved for men?

DWM I see her as actually having been liberated by the depression, because she was raised in a family where people played the piano. She lived with an aunt who had money and who got her a very good musical education, thinking she would become a concert pianist or possibly a piano teacher – someone who could have an artistic career. That aunt who raised her was herself quite an interesting woman…she owned race horses and had hotels in the red light district in Kansas City, which is where Dorothy got her musical education. Kansas City at that time was the absolute center of jazz because they just didn’t have prohibition in Kansas City…

JJM Yes, that’s where Lester Young and Count Basie and Charlie Parker were playing in those days…

DWM That’s right, and Mary Lou Williams too. There were female musicians, of course, and good ones. There was jazz all around Dorothy in Kansas City and she taught herself. Her brother was not clear whether she ever had lessons on the saxophone. She was a very good musician, one who practiced all the time. She was from a very respected family. The depression started changing things around, and when Dorothy was old enough to get away from her aunt, she went back to Oklahoma City and started looking for work as a piano player. She found she couldn’t get work as a female, as playing in bars was not thought to be a place for a lady to be…

JM If she had grown up somewhere other than that part of the country – Oklahoma, Missouri – like Oakland or Pittsburgh, would this story ever have happened?

DWM Probably not. Oklahoma City, at the time Dorothy started playing the piano, was oil rich. The place that supported a musician’s life during the depression was bars, because people came to dance on bars Bar culture supported the life of the musician, long before there were night clubs or radio. Musicians would gravitate to where there was enough disposable income to spend in bars. That means large urban centers and it had to be a place where there was tolerance for people having a good time.

JM Not to mention tolerance for societal outcasts or for people who are different. It’s hard for me to imagine Oklahoma of the 1930’s being tolerant…

DWM Oklahoma is a very conservative place, but it is also a place with a lot of give and take. If you want things to go your way, you have to let people have things their own way too, so they don’t exercise their bigotry on each other. Oklahoma was a dry state well into the 1950’s, but there were always places that were under the control of sheriffs and elected officials where drinking would go on. There was graft, corruption – in other words, there was protection placed on those serving alcohol. So, there were these parts of Oklahoma City where it was well known that you could always get a drink, and that’s where the nightclubs were.

JM Dorothy’s childhood seemed to be surrounded by men incapable of doing the right thing for their wives and children. Was her cross-dressing an opportunity to do the right thing as a male for the family?

DWM I don’t think so. I think Dorothy actually put on men’s clothes for the first time because she wanted to get an audition.

JJM So it was that simple? She needed the work?

DWM Yes. I also think that she really liked it. She was an unconventional person. She liked to joke, she liked fooling people, clearly. There was a “high” in it for her. I didn’t use the word “lesbian” about Dorothy in my book, but Dorothy never had anything but girlfriends. I think she was discovering her own sexuality at the same time that she started getting work as a musician, and finding that the only way to get work was to wear guy’s clothes. I think that she found that the adapting she had to do to get a job put in her way other kinds of things she had a taste for too, and that she fell into the life of a show person. The show business world was definitely not conventionally bourgeois, and had always been full of artistic types.

JJM She also had a quite an introduction to the show business world through the Teagarden family. She was in a rooming house run by Jack Teagarden’s mother?

DWM Yes, Jack Teagarden’s mother Helen and her family moved up from Texas to Oklahoma City after Jack’s father died. Helen ran a boarding house there. Jack Teagarden was on the road at a very early age – 16 I believe – but he always came back to see his mother, so there were musicians coming and going through the boarding house all the time. Dorothy had a room in that rooming house during 1934, and was very well remembered by Norma Teagarden, Jack’s sister. She knew Dorothy was female who just wore men’s clothes, and Norma didn’t really know what to say about it. Norma had more chances to get work because of the family she came from. In any case, the Teagarden’s were really the centerpiece of the music business in Oklahoma City, and Dorothy (Billy) Tipton was living right in that house. Later, Billy used to say that she played music with Jack Teagarden. She (Dorothy) had probably sat in when Jack was visiting his mother.

JJM It was during this time that Dorothy met a woman named Non-Earl. That was Billy’s first love, correct?

DWM Yes, absolutely. Non Earl was a real party girl. She was described by the musicians that remembered them as an ‘older woman’. Billy was 16 or 17, and Non Earl was 30. She was definitely in her prime when she met Billy. She had been a dancer in marathons in the early part of the depression, so she knew all the musicians and the bands. She would be what they called a “kitty girl”, and she would go around and pass the hat and get people to make requests and share the money with the band. It’s quite clear that she and Billy hit it off…they lived together for six years or so.

JJM Was she the only love of Billy’s life that really knew from the start that Billy was female?

DWM Probably so. Non Earl died in 1967, so she was not available for an interview, but if there were one person I wish I could have gotten to know, it would have been her. She was my favorite character. I think she introduced Billy to her considerable sexual expertise, and Billy learned her oral sex techniques from Non Earl. But also, I think that Non Earl must have liberated in Billy her own sexual confidence. I think Billy must have enjoyed sex a good deal…

JJM As long as he kept his corset on, and he kept the lights out…

DWM But that was only later, when I was able to talk to women who had sex with Billy who didn’t know that Billy was female. That meant, of course, Billy taking big risks. At one point, I was interviewing a woman who had been known as Mrs. Tipton, Maryann, and I said to her, “What did you think Billy was using? Did you think he had some kind of dildo?” She said, “Honey, I can hardly wait to read your book. I thought it was a penis!” Clearly Billy had an active sex life, and he practiced some kind of penetration with them that was very gratifying and that they never doubted that it was a man.

JJM Billy and Non Earl moved from Oklahoma City to Joplin, Missouri. Did they make this move to get away from an area where Billy would be so easily recognized?

DWM Well, this is all speculation, of course…Billy was a good enough musician to get a job in a swing band, particularly since a lot of musicians were off to war. Billy claimed to have been damaged in a car accident, where his ribs were crushed and had to wear bindings. But he made a very good-looking guy, glamorous, really, and rather easily got a job in a nightclub in Joplin called the Cotton Club. By then, Non Earl was not a great asset for Billy, and I think he just kind of shed her and moved on to more glamorous younger women.

JJM Yes, and as you said, he made a good-looking man, and his initial trials as a man were quite successful in attracting women. His woman friend that he made after Non Earl was an 18 year old named June, and she was the first woman to claim she didn’t know she was involved with a cross dresser.

DWM Yes, although she later told Billy’s brother that she had found out about this.

JJM How did she find out?

DWM I don’t know, and I was never able to find June. Billy’s brother (also named William) only had the memory of her telling him, and talking to him about Billy. Billy’s brother was not happy about this, he was a very respectable engineer, and was embarrassed by Dorothy’s life and choices and rather unforgiving of the way he thought she dishonored the family. But he was very dutiful in Billy’s memory, and in the conversations that he had with me I think he tried to come to some sort of understanding of what would have motivated his sister to do these things. So, he didn’t have clear or full or fluent sorts of memories that he would share with me. I had to know quite a lot before he would respond and confirm what I had to say or ask him about…He didn’t volunteer much.

JJM I have to assume that there was some bitterness around this. Of all the names Dorothy could have named herself, to name herself the same name that her brother…why not David or Ralph or something? Her father’s name was William…

DWM Yes, her father was a very well known aviator in Oklahoma City, and he named his only son, Dorothy’s brother, after him, so, Dorothy just took the name. It is an androgynous name, and it’s a good jazz name.

JJM There was another interesting character that you wrote about in the book, and this goes back to when they were in Oklahoma City. One of the first bands Billy was a part of was called the Banner Cavaliers, an imitation Bob Wills and the Texas Playboys. There was a character who was the station manager at the radio station where the band played whose name was Buck, who herself was a cross dresser. What was that all about?

DWM Yes, wasn’t that wild? I think one of the things that I got out of these guys when I expressed my amazement at it, more than once, I was taken aside and told that there were the “straight” people, and there were the “show” people, as in entertainers. In the world of the show people, you got a lot of variety, and who cares if people are different. To them, that was the explanation of all of this. If we take a sort of educated, late 20th Century look at the study of gay culture, it is really fairly well understood that it has always survived in show places – that is people who gravitate to it from the arts are people who frequently have an ambiguous or multiple sexuality as part of their creativity, that the arts are the “place of this”, and that cultural space has always been allotted to them. So, Buck was a character, as people would say, and she had her perfect niche doing these radio broadcasts where she would bring live musicians in. Everyone was quite fascinated about the spectacle of Buck…

JJM There are so many interesting characters in this story, but I guess no matter what someone’s sexual preference, if you do a biography on a show person, you are going to have these kinds of stories…

DWM It’s true that people are really different from what you think they are. That’s another delightful thing about writing biography – people are so opaque and so full of secret places.

JJM During the Joplin, Missouri days, Billy left June and took up with another woman named Betty. They went west to the Portland, Oregon area. The West Coast at that time was an up and coming jazz area. What did he hope to do with his career as result of coming west?

DWM He went west to work with a guy he got acquainted with in Joplin, who was a Texan, and was the bandleader of the band Billy was with, George Mayer. Meyer was more of a mover and shaker than Billy was at the time. The two of them were very complimentary. They both were “goof-offs”, and they worked together very well. They had the same kind of charm and both were fastidious dressers. They had a lot to hide, each of them. Apparently, George never did know that Billy was female. He must have been so totally self-absorbed that they didn’t notice the existence of others, and I think this was the type of person Billy chose to be around. George went out west and had developed a tour circuit. He got in touch with Billy and asked him if he would come and work with him. I also think that things got a bit uncomfortable for Billy if he was in one place too long. I never was able to actually put my finger on any experience of the kind that I know he must have had, which is people coming up to him, saying “I know what you are doing.” I am sure some people must have known and given him a hard time. There were real opportunities that sprang up on the West Coast during the Second World War because of all the nightclubs that opened near the shipyards and army bases. There were enough clubs to make a circuit for a musician. They would never be any place for more than a couple of weeks. The Portland area was a very good one.

JJM He also went to LA for a little while, and one of the important things that happened to him was that he was on television for 15 minutes in Santa Barbara, long enough for an executive from Tops Records to see him. He liked him and got him involved in some sort of a contract creating easy listening records. Was this fulfilling his promise or did he basically take what he could get at this point?

DWM They all thought that if you got one record contract, you got more. It was good experience. I talked to two other members of the trio who are still living about this episode, and they were very excited about it, but the record company they were recording for would sell records “by the yard” in department stores, where the equipment was sold. In a way, it was viewed as generic music and it was never going to make him into a star. Still, there was always the thought that this was like a step in a ladder.

JJM Reading that a couple of his heroes at that time were Chet Baker and Art Pepper…these guys were hardly following the same path that Billy was in virtually every aspect of their lives…

DWM Baker was an Oklahoman…

JJM True. That may be part of why Billy identified with him. The record he recorded looked as if it were made specifically for discounters like White Front department stores. I have to imagine that was a stepping stone for Billy, or it was the only thing he could get.

DWM Billy really did have a hard time making a living, too. He was a very professional and disciplined man, but he never had a lot of money, he lived on what he had.

JJM You mean the $31 he made in royalties on his record wasn’t enough to sustain him? Billy was offered jobs in larger communities, one being Reno, Nevada. My sense of it is that people in more sophisticated communities saw through Billy. For example, you mentioned how San Franciscans knew right away they were dealing with a woman dressed as a man. Did he feel that being in a community like Reno would expose him, therefore he wanted to get back to a simpler environment?

DWM At the time he turned down a contract to play in Reno, the city was just being built. It was being built by the mob! They did background checks, and it was not going to be easy to pass as a man there. There would be a lot of scrutiny before getting a job in a nightclub. There was also the fact it was really on the road between Oklahoma and Los Angeles. People would drop by, and he would tend to get run into by people who used to know him in his past. There was also the increasing sophistication of the audiences. I think Billy decided he had better stay out of the way of fame. Moving to Spokane, Washington, where he had a job offer from the guy who had been managing him, his booking agent, Dave Sobol, he decided that would be a good thing to do.

JJM His playing days, slowly but surely started dwindling, although there was a time where he was earning some pretty good money between the commissions he made at the talent agency and the $800 or so he was making in performance fees. In those days, late 50’s, early 60’s, that was a pretty good living.

DWM Yes, it wasn’t bad. He did a lot of jobs. He was interested in settling down. He bought a nice house in Spokane in a very nice part of town and started adopting children with his wife, Kitty, who had been a stripper. She quit the business to become a homemaker. So, I think what he wanted was a nice middle class life.

JJM The adoptions were at his urgency…

DWM Yes, and they were arranged by Kitty, with women who had illegitimate children who were in show business too, and who wanted to give them up. The first son was adopted at birth. The second son adopted when he was a couple years old, and the third son was adopted at birth.

JJM Billy and Kitty were married for 18 years, and there was a series of situations revolving around physical and emotional trauma that Kitty experienced as a child that really required a physical separation. They not only slept in separate bedrooms, but on different floors of the house. Did that simplify Billy’s life?

DWM Kitty thought that Billy was only ten years older than she was, but Billy was actually 20 years older. She told me in one of her interviews, “You know, when I finally heard about Billy, I thought, ‘My god, when we got married he must have been going through menopause!'” I also thought that Billy was probably ready to just retire at that point.

JJM How many different women did you interview that he was married to?

DWM Three.

JJM Did they feel embarrassed by this at all? Did they feel silly having to admit to you that she is going to write a book and expose how I didn’t know that this guy I was married to was actually a woman?

DWM Of course they were! But I wasn’t the first person that had talked to them about this. They had been sought out by the journalists. I think I benefited by showing them that I am not a journalist, that I was interested in their own accounts of their own lives and how that fits into the story. The thing that was quite appealing to me about this whole story is that Billy did not make enemies, even of these women that he deceived. First of all, it was a kind of funny class issue. One has to think about the glamour of the performer. Even though this was pretty small time stuff, still a guy on the bandstand who was good looking and cool, nicely dressed and flirtatious, and he turns his eye on “you”, you like being admired like that, by someone like Billy. He had an air of superiority over these young women – party girls – they were delighted, they were flattered by Billy’s attention. They were also good-hearted women who really seemed to enjoy themselves. Billy was good to them. He had a good education, was well spoken. He was a man who had a rather superior education…He made the rules in the house. He insisted on his privacy. None of the women who thought of this afterward felt his requirements were abusive, or doing something fundamentally dishonest to them. It was very odd, they did not feel deceived in any way.

JJM Towards the end of the book, you write about how the final straw of Billy and Kitty’s marriage was around their differences in how the children should be raised. Billy was, if anything, lacking in rules and discipline around his children. He didn’t really know how to handle his kids…

DWM He was very permissive. He was also kind of indifferent to their problems. He always wanted to be liked. He certainly exercised a lot of discipline in his work life, but that was partly his survival technique. He never drank, was professionally very reliable, had guys under him who wouldn’t contest his masculinity. He chose people around him who were going to follow in line. With the kids it was different. I don’t think he was a particularly good parent, but he was a loving person. I think they got from that the kind of nurturing that can be.

JJM There was an interesting observation from one of Billy’s friends, a magician, who said “Billy Tipton should have received an Academy Award for the Best Actor of All Time.” When it’s all said and done, that’s what he was, an accomplished actor…

DWM I agree. I think that Billy really had two very large talents, and one of them was musicianship and the other was for mimicry and impersonation. I really got interested in that while I was working on the book because my husband’s grandson, from the time he was about 10 years old, has been immensely interested in magic, and is very good at it. I discovered that it is rather easy to fool people, if you are good at that sort of thing! Billy really was a master…

JJM Are you happy with the results of the book?

DWM Yes, I am quite pleased, and I was happy to hear that the book is being taught in a course on The History of Sex in America.

JJM That is an accomplishment the rest of us can only fantasize about!



A Billy Tipton Timeline

Diane Wood Middlebrook products at Amazon.com



If you enjoyed this interview, you may want to read our interview with jazz critic Francis Davis.


Other Jerry Jazz Musician interviews


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