Dorothy Tipton was born in Oklahoma City but grew up in Kansas City, Missouri, where she was raised by an aunt after her parents' divorce. After the divorce, she rarely saw her father, G.W. Tipton, a pilot who sometimes took her for airplane rides. As a high school student, she went by the nickname "Tippy" and became interested in music, especially jazz. She studied piano and saxophone, but her school had a policy forbidding girls to play in the school band. She returned to Oklahoma for her final year of high school and joined the school band there.
In 1933, Tipton began dressing as a man, which allowed Tipton to blend with the other members of the jazz bands with whom Tipton played in small Oklahoma bars. Career opportunities for women in jazz were limited. As Tipton began a more serious music career, Tipton adopted her father's nickname, Billy, and more actively concealed her female body by breast-binding and packing. At first, Tipton only presented as male in performance, but by 1940 Tipton was living as a man in her private life as well. Two of Tipton's female cousins, with whom Tipton maintained contact over the years, were the only persons privy to both sides of Tipton's life.
Tipton gradually gained success and recognition as a musician. In 1936, Tipton was the leader of a band playing on KFXR. In 1938, Tipton joined Louvenie’s Western Swingbillies, a band which played on 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, Missouri's Cotton Club with George Mayer'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 George Mayer. While this tour was far from glamorous, the band's appearances at Roseburg, Orgeon'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 Mayer's band became more successful, they began getting more prestigious work, performing with The Ink Spots, the Delta Rhythm Boys, and Billy Eckstine at the Boulevard Club in Coeur d'Alene, Idaho.
Tipton began playing piano alone at the Elks club in Longview, Washington. In Longview, he started the Billy Tipton Trio, which consisted of Tipton on piano, Dick O'Neil on drums, and Kenny Richards (and later Ron Kilde) on bass. Richards later said that he had no idea that Tipton was anything other than male. The trio gained in 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 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 was the house band at Allen's Tin Pan Alley, performing 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 like Liberace and Elvis Presley. In some of these sketches, he played a little girl, and though he never impersonated an adult woman, he would make jokes about homosexuality. He mentored young musicians at the Dave Sobol Theatrical Agency.
In the 1970s, worsening arthritis forced Billy Tipton to retire from music.
As noted, early in his career, Tipton cross-dressed only professionally, continuing to present as a woman otherwise. He spent those early years living with a woman named Non Earl Harrell, in a relationship which other musicians thought of as lesbian. The relationship ended in 1942. His next relationship, with a singer known only as "June", lasted for several years.For seven years, Tipton lived with Betty Cox, who was nineteen years old when they became involved. According to Betty, they had a heterosexual relationship. Betty remembered him as "the most fantastic love of my life." Tipton kept the secret of his biological gender from Betty by inventing a story that he had been in a serious car accident which had badly damaged his genitals and broken some ribs, and that to protect the damaged chest he had to bind it. From then on, this was what he would tell the women in his life.
After Betty ended their relationship, he quickly became involved with Maryann Catanach, a prostitute. According to Maryann, theirs was a normal sexual relationship, and she did not know that Tipton was biologically female, since he dressed in private, had sex only in the dark, and preferred to touch, not to be touched.
In 1960, he ended this relationship to settle down with nightclub dancer and stripper Kitty Kelly (later known as Kitty Oakes), who was known professionally as "The Irish Venus." Tipton was never legally married, but several women had drivers' licenses identifying them as Mrs. Tipton. Kitty said that they never had sex but had an otherwise normal life. They were involved with their local PTA and with the Boy Scouts. They adopted three sons, John, Scott, and William. After Tipton's death, Kitty gave several interviews about him and their relationship. In early interviews she said “He gave up everything,” “There were certain rules and regulations in those days if you were going to be a musician,” in reference to breaking into the 1920-30's music industry as a woman, and “No one knew. It was the best-guarded secret since Houdini.” But in later interviews she denied having known that Tipton was a trans man, a denial that sons John and Scott did not believe. William described Tipton as a good father who loved to go on Scout camping trips.
Their adopted sons became difficult to manage during their adolescence. Because of the couple's ongoing arguments over how they should raise the boys, Tipton left Kitty, moved into a mobile home with their sons, and resumed his old relationship with Maryann. He remained there, living in poverty, until his death a year later.
In 1989, at the age of 74, he had symptoms he attributed to emphysema and refused to call a doctor. In actuality he was suffering from a hemorrhaging peptic ulcer, which, untreated, was fatal. It was while paramedics were trying to save Tipton's life, with son William looking on, that William learned that his father was biologically female. Tipton was pronounced dead at Valley General Hospital. The coroner shared the revelation with the rest of the family. In an attempt to keep Billy's secret, Kitty arranged for his body to be cremated. But one of his 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 like National Enquirer and Star, as well as mainstream papers like New York Magazine and The Seattle Times. Tipton's family made talk show appearances.
Two wills were left by Tipton; one handwritten and not notarized which left everything to William Jr. and the second, notarized, leaving everything to Jon Clark. A court upheld the first will, and William inherited almost everything, with John and Scott receiving a dollar each.
The Billy Tipton Memorial Saxophone Quartet is an all-woman music group. Eventually they shortened the band's name to The Tiptons.
The 1991 song "Tipton" by folksinger Phranc is a tribute to Billy Tipton.
"Can't Help Lovin' Dat Man" is a 1995 short film based on the life and career of Billy Tipton.
"Stevie Wants to Play the Blues" was a play based on Tipton's life written by Eduardo Machado and performed in Los Angeles.
"The Slow Drag" was a play based on Tipton's life by Carson Kreitzer performed in New York City and London.
An opera based on Tipton's life, "Billy", was staged in Olympia, Washington.
Trumpet, a novel based on Tipton's life, is by Jackie Kay.
"The Opposite Sex is Neither," a theatrical revue by noted transwoman Kate Bornstein, features Billy Tipton.
"Billy's Thing" is an unreleased track by Jill Sobule.
"The Legend of Billy Tipton," by the punk band The Video Dead, is about the story of Billy Tipton. The song "Hot Topic" on Le Tigre's self-titled debut pays tribute to dozens of female visual artists, musicians, writers, feminists and others who have inspired them, including Tipton.