Harry Allen, born in 1882, from a young age identified and presented as male, he is notable as one-of the most publicized transgender men in the United States in the 1900s. He was an at-risk transgender youth best known for the publication of his antics and hardships by various Seattle newspapers between 1900 and 1922. He was publicly known as a gender non-conformist, a petty criminal and heartbreaker.

While Harry worked jobs that were generally regarded as ‘men’s’ jobs, such as farmhand, bartender and cowboy, he experienced profiling from police and was considered a vagrant and was hassled as such. Despite transphobic criticisms, newspapers still could not stop themselves from commenting on his handsome face and well-groomed appearance. His romantic antics were viewed with scrutiny as he had several public break-ups that led to his partners committing acts of romantic desperation in protest of their break-up, and the newspapers just ate it up. It is purported that Harry in his personal life was romantically inclined toward women and sexually inclined toward men and women, and also engaged in sex work.

In his later life, he lived with a woman who was considered and referenced to be his wife, due to the Mann law, he was incarcerated for a time but was later let go because Harry’s birth sex actually nullified the law from applying to him and his wife. He was interviewed in 1912 while incarcerated by Miriam Van Waters, an anthropologist and women's rights advocate, who determined that Harry’s criminal record was largely if not completely due to targeted policing and discrimination.