1. Lili Elbe (1882–1931)
Lili Elbe is perhaps one of the more famous trans women in the last few centuries. She was one of the first-known recipients of gender confirmation surgery. Lili began experimenting with dressing as a woman after her wife Gerda asked her to pose for a painting wearing women's clothing. Lili quickly realized how at home she felt dressing as a woman and began doing so full-time. She received several surgeries from 1930 to 1931 and died of complications from a failed uterus transplant. She was the second-known trans woman to undergo vaginoplasty. In 2015, Eddie Redmayne starred in the film adaptation of Lili's life titled The Danish Girl.
2. Dora Richter (1891–1933)
Dora began displaying more feminine desires and characteristics at a young age, and attempted to remove her penis at age 6. She was allowed to live as a female after this incident. Throughout her life, she was arrested several times for cross-dressing and was eventually referred to Dr. Magnus Hirschfeld, a Jewish German doctor who was studying the relationships between gender identity and biological sex and who had performed gender confirmation surgeries. Dora is the first-known trans woman to undergo gender confirmation surgery and the first to undergo vaginoplasty. In 1933, the Nazis attacked Institut für Sexualwissenschaft (translated as "Institute for Sexology"), the institute founded by Dr. Hirschfeld that also employed trans people. Dora perished in the attack.
3. Lucy Hicks Anderson (1886–1954)
Lucy Hicks was one of the first-known Black trans women. She was born in Kentucky and wanted to present as a girl from a very young age. Surprisingly, a doctor recommended she be raised as a girl to offset the gender dysphoria. She fought for her own marriage equality, as she had been accused of lying under oath for not disclosing she was born male. She was quoted in saying, "I defy any doctor in the world to prove that I am not a woman."
4. Coccinelle (1931–2006)
Coccinelle was a French actor and showgirl, and was one of the first trans women to receive hormone replacement therapy and undergo gender confirmation surgery. Her surgery and marriage led France to not only allow trans people to marry but also allow trans people to alter their birth certificates after undergoing gender confirmation surgery. Coccinelle later founded a number of trans-related organizations.
5. Christine Jorgensen (1926–1989)
Christine Jorgensen was a World War II veteran who began transitioning after military service. She received several surgeries and, upon returning to the United States, was instantly famous. She went on to perform as an actor and nightclub entertainer, as well as a singer. She spoke on being transgender and wrote an autobiography in 1967, and was considered the first transgender celebrity in the United States.
6. Jack Bee Garland (1869–1936)
Jack Bee Garland, also known as Beebe Beam, joined the US Army in 1899. While accompanying the army in the Pacific theater of the Spanish-American War, he was discovered as having been born a female by the captain of his ship and wasn't allowed to board the ship again. His fellow soldiers hid him on board until they were sailing away from Hawaii. He spent time in the Philippines working as a nurse and interpreter before returning to the United States and becoming an author. He spent the rest of his life doing charitable organizational work.
7. Dr. Alan Hart (1890–1962)
Dr. Alan Hart was born and raised in Oregon. As an adult, he sought medical assistance to help him transition and live as a man full-time. Dr. Joshua Gilbert eventually performed a full hysterectomy on Hart to prevent pregnancy and stop menstruation, although synthetic testosterone wasn't yet available. After the surgery, Dr. Hart went on to get married, publish several books, and have two medical practices. He is best known for his work as an epidemiologist whose research helped diagnose and treat tuberculosis cases, lowering the death toll significantly. After World War II, Dr. Hart was able to begin hormone replacement therapy, which allowed his voice to deepen and facial hair to grow.
8. Reed Erickson (1917–1992)
Reed Erickson inherited his family's businesses in 1962 at age 50 and ran them successfully throughout the decade. He began his transition under the care of Dr. Harry Benjamin the following year and two years later founded the Erickson Educational Foundation. His foundation later funded numerous other organizations, including the Harry Benjamin International Gender Dysphoria Association (now known as the World Professional Association for Transgender Health).
9. Dr. Michael Dillon (1915–1962)
A British physician, Michael Dillon is considered the first trans man to undergo phalloplasty and receive testosterone therapy. He was also likely the first trans man to have a double mastectomy. In 1946, he published a book titled Self: A Study in Ethics and Endocrinology, in which he discussed being a trans man and the idea that it is innate and can only be treated through medical transition.
10. Lou Sullivan (1951–1991)
Perhaps one of the more influential trans men of the 20th century, Lou Sullivan not only helped form a community for trans masculine people, but he also helped make it easier for trans men to transition. Previously, being homosexual excluded trans men from receiving gender confirmation surgery. Lou fought this and made it possible for other gay trans men to obtain surgery services as part of their transition. He began taking testosterone in 1979 and had genital reconstruction surgery in 1986. He also founded FTM International, an organization specifically devoted to supporting female-to-male individuals, and was diagnosed with AIDS later the same year. He died in 1991 from AIDS-related illness.