Billy Tipton

Today, we add a representative of yet another group of people in our list: Billy Tipton is our first trans male artist.

Born Dorothy Lucille Tipton in Oklahoma City, Oklahoma, in 1914, Tipton grew up in Kansas City, Missouri, where he was raised by an aunt after his parents' divorce. 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, studying piano and saxophone. He returned to Oklahoma for his final year of high school and joined the school band there.

As Tipton began a more serious music career, he adopted his father's nickname, Billy, and more actively worked to pass as male by binding his breasts and padding his pants. At first, Tipton only presented as male in performance, but by 1940 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. In 1938, he joined Louvenie's Western Swingbillies, a band that 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 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 George 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.

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. 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.

From the first album, here's Sweet Georgia Brown:

And here's Don't Blame Me:

Finally, here's The Man I Love:

From the second album, here's Begin The Beguine:

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 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.

Early in his career, Tipton presented as a male 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 that other musicians thought of as lesbian. The relationship ended in 1942. 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." Tipton kept the secret of his extrinsic sexual characteristics from Betty by inventing a story of having been in a serious car accident resulting in damaged genitals and broken ribs, and that it was necessary to bind the damaged chest to protect it. From then on, this was what he would tell the women in his life.

Tipton was never formally married in a ceremony, but several women had drivers' licenses identifying them as Mrs. Tipton. In 1960, Tipton ended his relationship with Cox to settle down with nightclub dancer and stripper Kitty Kelly (later known as Kitty Oakes), who was known professionally as "The Irish Venus". 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 1920−30s music industry. William described Tipton as a good father who loved to go on Scout camping trips.

Because of the couple's ongoing arguments over how they should raise the boys, Tipton left Kitty in the late 1970s, moved into a mobile home with their sons (two of their sons had run away from home after being physically abused by Kitty), and resumed an old relationship with a woman named Maryann. He remained there, living in poverty, until his death.

In 1989, at the age of 74, Tipton had symptoms he attributed to emphysema and refused to call a doctor. He was actually 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 had female anatomy. Tipton was pronounced dead at Valley General Hospital. The coroner shared this with the rest of the family. In an attempt to keep the secret, Kitty arranged for his body to be cremated, but later after 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 more reputable papers such as New York Magazine and The Seattle Times. Tipton's family even made talk show appearances.

Two wills were left by Billy Tipton: 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), which, after lawyers' fees, amounted to $35,000 for each son.

There were works of art inspired by Tipton's life. The 1991 song "Tipton" by folksinger Phranc was one of them:

Can't Help Lovin' Dat Man is a 1995 short film based on his life and career. 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 is a novel by Jackie Kay inspired by Tipton's life. The Opposite Sex Is Neither, a theatrical revue by noted trans woman 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 was about his life. A band was formed that called themselves The Billy Tipton Memorial Saxophone Quartet. Kill Me, Por Favor is a short story including a section about Billy Tipton in Ry Cooder's book Los Angeles Stories.

Finally, the singer-songwriter and cabaret artist Nellie McKay performed an original biographical show about Tipton, "“A Girl Named Bill—The Life and Times of Billy Tipton,” at the New York nightclub 54 Below on August 5–9, 2014. Here's an excerpt:

Billy Tipton didn't have a huge career, but his unusual life managed to inspire a lot of people and became an important part of the LGBTQI legacy.