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William Lee Tipton (December 29, 1914 – January 21, 1989) was an American jazz musician, bandleader, and talent broker. For decades, Tipton assumed a male gender identity. Tipton's female birth sex was not publicly revealed until after his death, and the revelation came as a surprise to family and friends.
Tipton's music career began in the mid-1930s when he led a band for radio broadcasts. He played in various dance bands in the 1940s and recorded two trio albums for a small record label in the mid-1950s. Thereafter, he worked as a talent broker. Tipton stopped performing in the late 1970s due to arthritis.
Born Dorothy Lucille Tipton in Oklahoma City, Oklahoma, Tipton grew up in Kansas City, Missouri, where he was raised by an aunt after his parents divorced when he was four. He subsequently rarely saw his father, G. W. Tipton, a pilot who sometimes took him for airplane rides. As a high school student, Tipton went by the nickname "Tippy" and became interested in music (especially jazz), playing piano and saxophone. As a female, Tipton was not allowed to join the school band at Southwest High School. He returned to Oklahoma for his final year of high school and joined the school band at Connors State College High School.
In approximately 1933, Tipton started binding his breasts and dressing as a man to fit in with the typical jazz band image of the era. As Tipton began a more serious music career, he "decided to permanently take on the role of a male musician", adopting the name Billy Lee Tipton. By 1940, Tipton was living as a man in private life as well. Two of Tipton's female cousins, with whom Tipton maintained contact over the years, were the only persons known to be privy to Tipton's assigned sex.
In 1936, Tipton was the leader of a band playing on KFXR radio. In 1938, Tipton joined Louvenie's Western Swingbillies, a band that played on radio KTOK and at Brown's Tavern. In 1940 he was touring the Midwest playing at dances with Scott Cameron's band. In 1941 he began a two and a half-year run performing at Joplin's Cotton Club with George Meyer's band, then toured for a time with Ross Carlyle, then played for two years in Texas.
In 1949, Tipton began touring the Pacific Northwest with Meyer. While this tour was far from glamorous, the band's appearances at Roseburg, Oregon's Shalimar Room were recorded by a local radio station, and so recordings exist of Tipton's work during this time, including "If I Knew Then" and "Sophisticated Swing". The trio's signature song was "Flying Home", performed in a close imitation of Benny Goodman's band.
As George Meyer's band became more successful, they began getting more work, performing at the Boulevard Club in Coeur d'Alene, Idaho, sharing the bill with others such as The Ink Spots, the Delta Rhythm Boys, and Billy Eckstine.
Tipton began playing piano alone at the Elks club in Longview, Washington in 1951. In Longview, he started the Billy Tipton Trio, which included Dick O'Neil on drums, and Kenny Richards (and later Ron Kilde) on bass. The trio gained local popularity.
During a performance on tour at King's Supper Club in Santa Barbara, California, a talent scout from Tops Records heard them play and got them a contract. The Billy Tipton Trio recorded two albums of jazz standards for Tops: Sweet Georgia Brown and Billy Tipton Plays Hi-Fi on Piano, both released early in 1957. Among the pieces performed were "Can't Help Lovin' Dat Man", "Willow Weep for Me", "What'll I Do", and "Don't Blame Me". In 1957, the albums sold 17,678 copies, a "respectable" sum for a small independent record label.
After the albums' success, the Billy Tipton Trio was offered a position as house band at the Holiday Hotel casino in Reno, Nevada, and Tops Records invited the trio to record four more albums. Tipton declined both offers, choosing instead to move to Spokane, Washington, where he worked as a talent broker and the trio performed weekly. He played mainly swing standards rather than the jazz he preferred. His performances included skits in the vaudeville tradition, in which he imitated celebrities such as Liberace and Elvis Presley. In some of these sketches, he played a little girl. He mentored young musicians at the Dave Sobol Theatrical Agency.
In the late 1970s, worsening arthritis forced Tipton to retire from music.
Tipton was never legally married, but there were five women who called themselves Mrs. Tipton at various points. In 1934, Tipton began living with a woman named Non Earl Harrell in a relationship that other musicians thought of as lesbian. The relationship ended in 1942. Tipton's sex was reportedly concealed from the four women who would later call themselves "Mrs. Tipton". Tipton kept the secret of his extrinsic sexual characteristics from them by telling them he had been in a serious car accident that resulted in damaged genitals and broken ribs.
Tipton's next relationship, with a singer known only as "June", lasted for several years. For seven years, Tipton lived with Betty Cox, who was 19 when they became involved. Cox remembered Tipton as "the most fantastic love of my life." In 1954, Tipton's relationship with Cox ended, and he then entered a relationship with a woman named Maryann. The pair moved to Spokane, Washington in 1958. Maryann later stated that in 1960, she discovered that Tipton had become involved with nightclub dancer and stripper Kitty Kelly.
Tipton and Kelly settled down together in 1961. They adopted three sons, John, Scott, and William. After they separated in the 1970s, Tipton resumed a relationship with Maryann. Maryann reportedly discovered Tipton's birth certificate and asked Tipton about it once, but was given no reply other than a "terrible look".
In 1989, at the age of 74, Tipton had symptoms which he attributed to the emphysema he had contracted from heavy smoking and refused to call a doctor. He was actually suffering from a hemorrhaging peptic ulcer which, untreated, was fatal. While paramedics were trying to save Tipton's life, his son, William, learned that his father was a transgender man. This information "came as a shock to nearly everyone, including the women who had considered themselves his wives, as well as his sons and the musicians who had traveled with him". In an attempt to keep Tipton's biological sex a secret, Kitty arranged for his body to be cremated; later, following financial offers from the media, Kitty and one of their sons went public with the story. The first newspaper article was published the day after Tipton's funeral and it was quickly picked up by wire services. Stories about Tipton appeared in a variety of papers including tabloids such as National Enquirer and Star, as well as People, New York Magazine and The Seattle Times. Tipton's family even made talk show appearances.
Tipton left two wills: one handwritten and not notarized that left everything to William Jr.; and the second, notarized, leaving everything to John Clark, the first child the Tiptons adopted. A court upheld the first will, and William inherited almost everything, with John and Scott receiving one dollar each. According to a 2009 episode of the documentary program The Will: Family Secrets Revealed, which featured interviews with all three sons, it was revealed that a final court judgment awarded all three sons an equal share of his wife Kitty Tipton's estate (not Billy Tipton's), which, after lawyers' fees, amounted to $35,000 for each son.