Billy Lee Tipton (December 29, 1914 – January 21, 1989) was an American jazz musician, bandleader, and talent broker. Tipton lived and identified as a man for most of his adult life; after his death, friends and family were surprised to learn that he was transgender.

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.

Assigned female at birth, Billy was originally named Dorothy Lucille Tipton. He was born in Oklahoma City on December 29, 1914. Tipton grew up in Kansas City, Missouri, where he was raised by an aunt after his parents divorced when he was four.^[2] As a high school student, Tipton went by the nickname "Tippy" and became interested in music (especially jazz), playing piano and saxophone.^[2] Tipton was not allowed to join the all-male 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.^[2]

Around 1933, Tipton started binding his breasts and presenting stereotypically masculine traits.^[3] 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.^[2] By 1940, Tipton was living as a man in private life as well.^[3]

Tipton was never legally married, but five women called themselves Mrs. Tipton during his life.^[3] In 1934,^[3] Tipton began living with a woman named Non Earl Harrell.^[7] The relationship ended in 1942.^[7][8] Tipton's sex was reportedly concealed from the four women who would later call themselves "Mrs. Tipton".^[3] 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.^[2]

Tipton's next relationship, with a singer known only as "June", lasted for several years.^[8] For seven years, Tipton lived with Betty Cox, who was 18 years old when they became involved. Cox remembered Tipton as "the most fantastic love of my life".^[5][9] In 1954, Tipton's relationship with Cox ended, and he then entered a relationship with a woman named Maryann.^[8] The pair moved to Spokane, Washington, in 1958. Maryann later stated that in 1960, she discovered that Tipton had become involved with nightclub dancer Kathleen "Kitty" Kelly.^[8]

Tipton and Kelly settled down together in 1961.^[8] They adopted three sons, John, Scott, and William;^[5] the adoptions were not legally recognised.^[10] After they separated around 1977, Tipton resumed a relationship with Maryann.^[8] Maryann reportedly discovered Tipton's birth certificate and asked Tipton about it once, but was given no reply other than a "terrible look".^[8]

In 1989, 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, left untreated, was fatal. On January 21, 1989, his son William called emergency services. While paramedics were trying to save Tipton's life, they, alongside Tipton's son William, discovered he was born female. 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".^[1][5] Later, following financial offers from the media, Kelly and one of their sons went public with the story.^[11] The first newspaper article was published the day after Tipton's funeral and it was quickly picked up by wire services. Stories about him appeared in a variety of papers, including tabloids such as National Enquirer^[12] and Star^[13] as well as People,^[14][15] The New York Times^[16] and The Seattle Times.^[10] Members of Tipton's family made talk show appearances as well.^[13][11][17]

Tipton left 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.^[11] A court upheld the first will, and William inherited almost everything, with John and Scott receiving one dollar each.^[18] 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.^[19] Two of his adopted sons changed their names not long after learning of Tipton's assigned gender, as they felt Tipton behaved deceptively.^[10]

• Stevie Wants to Play the Blues was a play based on Tipton's life written by Eduardo Machado and performed in Los Angeles, directed by Simon Callow and starring Amy Madigan and Paula Kelly.^[20][21]
• "The Legend of Billy Tipton", by the punk band The Video Dead, is about the story of Billy Tipton.^[22]
• Soita minulle Billy (Call me Billy), a Finnish play with Joanna Haartti playing Tipton, presented at Theatre Jurka in 2011^[23] and again at the 2012 Helsinki Festival.^[24]
• The Slow Drag (1996), by Carson Kreitzer, a "jazz cabaret" with a live band onstage featuring the character, Johnny Christmas, based on Tipton.^[25][26][27]
• Trumpet, a 1998 novel by Jackie Kay, tells the story of fictional Scottish jazz musician Joss Moody, inspired by Tipton.^[28]
• The Tiptons Sax Quartet, previously known as The Billy Tipton Memorial Saxophone Quartet, is a jazz saxophone quartet from Seattle, Washington. The name of the quartet was inspired by Tipton.^[29]
• A cabaret musical called A Girl Named Bill, starring Nellie McKay, tells the story of Tipton.^[29]
• No Ordinary Man, a documentary film about Tipton by Aisling Chin-Yee and Chase Joynt, premiered at the 2020 Toronto International Film Festival.^[30]

• Sweet Georgia Brown (LP). Billy Tipton Trio. Los Angeles: Tops Records. 1957. OCLC 55858361. L1522.
• Hi-Fi on Piano (LP). New York: Tops Records. 1957. OCLC 15877358. L1534.