Transgender people have always existed, but from the average history class, you wouldn’t know it. These ten pioneers are just a handful of trans men in history who made waves—from a revolutionary tuberculosis researcher to a powerful gospel singer.
Billy Tipton
American jazz musician and bandleader Billy Tipton started his career as the leader of a band playing on KFXR. He went on to tour the Midwest, play a two-year run at Joplin’s Cotton Club with George Meyer’s band, and tour the Pacific Northwest with George Meyer. In Longview, Washington, Tipton started the Billy Tipton Trio. Tipton was scouted by a talent agent in Santa Barbara, Calif. from Tops Records, and the Trio recorded two albums of jazz standards, which sold well for an independent record label. Tipton also performed skits on the vaudeville circuit, imitating celebrities like Liberace and Elvis Presley.
He also had several long-term relationships, including one with Kitty Kelly, a nightclub dancer. Though Kitty was lacking in the parenting department (she abused her adopted sons), Tipton was an involved father who loved to go on Boy Scout camping trips with his sons. Tipton died at age 74, and while paramedics were trying to revive Tipton, one of his sons learned he was transgender.
Alan Hart
Alan L. Hart was an American radiologist, physician, and tuberculosis researcher who pioneered the use of x-ray photography in tuberculosis detection. The tuberculosis screening programs he implemented saved countless lives. Hart was also one of the first documented transgender men to undergo surgical transition in the United States at the University of Oregon Medical School. Hart married Inez Stark, but when a medical school classmate outed him, the resulting blow to his career and financial strain took a toll on their marriage and she left him in 1923.
His second marriage to Edna Ruddick in 1925 lasted until the end of Hart’s life. After obtaining a master’s in public health from Yale, Hart moved with Edna to Connecticut, and she became a professor at the University of Hartford as he continued his work to fight TB. In addition to his medical research, Hart was a prolific writer. He published four novels and a number of short stories.
Willmer "Little Axe" Broadnax
Willmer Broadnax was a gospel quartet singer, known for his powerful tenor voice. He performed as a lead singer of Five Trumpets alongside future Soul Stirrer Paul Foster. Broadnax later joined the Spirit of Memphis Quartet, which recorded for King Records. He also worked with the Fairfield Four, and the Five Blind Boys of Mississippi. He headed a quartet called Little Axe and the Golden Echoes which released singles on Peacock Records. After his death in 1992, it was discovered Broadnax was transgender. Broadnax’s older brother, "Big Axe" Broadnax, was aware and stood by and sang with his brother.
Charley Parkhurst
Also known as One-Eyed Charley, Charley Parkhurst was an American farmer, rancher, and stagecoach driver in California. He was born in New England and raised in an orphanage, but ran away and took the name Charley. He followed the Gold Rush out west and built a reputation as one of the finest stage coach drivers on the West Coast. Parker was only outed after death.
Lou Sullivan
American author and activist Lou Sullivan is known for his trans rights activism, and for identifying as gay and trans. Sullivan was the editor of The Gateway newsletter produced by the Golden Gate Girls/Guys (later the Gateway Gender Alliance). He also wrote several guides for trans men, lobbied the American Psychiatric Association and World Professional Association for Transgender Health to remove sexual orientation from the criteria for gender identity disorder, and was a founding member of the GLBT Historical Society in San Francisco.
Dr. James Barry
A trailblazing physician and military surgeon, James Barry is renowned for being the first European recorded to perform a successful C-section in Africa, which both mother and child survived. Born in Ireland, Barry graduated from medical school in Edinburgh before serving in the British Army. His career was marked by his fierce advocacy for public health reforms, particularly in sanitation and care for marginalized groups. Though it wasn’t until after his death that it was discovered Barry was transgender, Barry’s life is a testament to resilience, brilliance, and the pursuit of justice in medicine.
Albert D.J. Cashier
Albert D.J. Cashier, a true Civil War hero, lived authentically despite societal constraints. Born in Ireland, Albert immigrated to the U.S. and enlisted in the Union Army, serving valiantly in several battles, including the Battle of Shiloh and the Siege of Vicksburg. Post-war, he continued living, working, and maintaining his identity until his passing. Albert's legacy highlights the courage to live one's truth, even in the harshest times.
Harry Allen
Known as “Harry Livingstone,” Harry Allen was a bold and unapologetic figure in early 20th-century Washington state. A trans man, Harry gained notoriety for run-ins with the law, including bar fights and drunkenness. He was also a notorious ladies' man, with several of his paramours reportedly ending their lives themselves following the heartbreak by Allen.
Arrested in 1911 in Spokane, Washington, the chief of the police tried to force Harry to wear feminine clothing, going so far as to threaten Harry with solitary confinement. He refused, choosing to wear his male garbs throughout his stay. Allen’s story is a powerful reminder of the resilience of trans men in history who dared to live as themselves despite societal backlash.
Karl M. Baer
A pioneering activist and trailblazer, Karl M. Baer was one of the first to undergo gender-affirming surgery in the early 20th century. Though born intersex and assigned female at birth, Karl came out as a trans man at the age of 19. Two years later, in 1906, he underwent surgery and later received gender recognition after having a new birth certificate issued.
Michael Dillon
Michael Dillon made history as the first trans man to transition using testosterone and phalloplasty procedures medically. A British physician and author, he wrote Self: A Study in Endocrinology and Ethics, advocating for compassionate care for trans individuals. Dillon’s journey from a deeply closeted life to a groundbreaking transition story inspires trans communities worldwide.