1. Ann Bonny and 2. Mary Read
Ann Bonny and Mary Read were 18th century pirates of the Caribbean. Irish-born Ann married a brigand named James Bonny as a teenager and moved from her home in South Carolina to the Caribbean, where she eloped with another pirate, Calico Jack Rackham. She dressed as a man to join his crew. Read was born in London and was passed off as a boy by her mother in order to collect child support from her dead half-brother's grandparents. After a stint with the British military, she married a sailor and began living as a woman. Her husband died young, and the widow Read once again disguised herself as a man and joined the military. Upon leaving the service, she drifted into a pirate's life. She met Ann Bonny while serving on Rackham's ship, and they became close friends, guarding each other's true identity. The entire pirate crew was captured in 1720, but Bonny and Read both won a stay of execution due to pregnancy. Read died in prison, possibly from childbirth complications. Bonny disappeared from court records. It is believed that her parents may have bought her freedom, but there are no official documents on her fate.
3. Hannah Snell
Englishwoman Hannah Snell served in the Royal Marines for four years in the 18th century. She assumed the identity of her brother-in-law James Gray after her child died and her husband deserted her. Her unit was sent to capture a French colony in India in 1748, and she was wounded several times without her sex ever being discovered. She revealed her secret to her shipmates in 1750 and was granted an honorable discharge and eventually a pension! Snell made the most of her experience. She sold her story to a publisher, appeared on stage in uniform to tell her story, and opened a pub called The Female Warrior.
More recent women posing as men, after the jump.
4. Frances Clayton
There are quite a few stories of women serving in the Civil War disguised as men. Estimates range from 150 to 400 such soldiers! Many distinguished themselves, and were even honored for their service after the war. One such hero was Frances L. Clayton, who wore men's clothing to enlist in the Union Army with her husband. She was wounded three times in battle, and was even taken prisoner by the Confederacy. After her husband was killed, she confided her sex to her commanding officer and was granted an honorable discharge.
5. Charley Parkhurst
Charley Parkhurst was known as one of the greatest stagecoach drivers of the Old West. Charley was short but strong, and even after retiring from driving, could outwork men half her age as a lumberjack. But after Charley died, those who had known "him" for years were shocked to discover Charley was a woman! Charlotte Darkey Parkhurst was born in New Hampshire in 1812. Dressed as a boy, Charley worked in stables and learned the craft of a driver. She built a reputation as a skilled driver, then fled to Georgia, possibly over the threat of exposure. She moved west to California in 1851, where she again built a reputation as a skilled and talented driver. At least once her secret was discovered, but those who knew kept it confidential to preserve her dignity. After her death in 1879, doctors not only discovered Charley's sex, but announced that she had at sometime in her life given birth! (image credit: Val Hoover)
6. Dorothy Lawrence
Dorothy Lawrence wanted to be a front line journalist during the first World War. Instead of enlisting under an assumed identity, she disguised herself as a British soldier and traveled to the front lines. She became a sapper with a mine-laying company! After ten days of laying mines, she became so nervous about her deception that she confessed to her commanding officer and was promptly arrested as a spy. Lawrence was forced to sign an affidavit agreeing not to write of her experiences, which defeated the entire purpose of her war effort. She actually did write of her experiences, but her story was not published in full until many years later. In 1925, Lawrence was committed to an insane asylum, where she lived until her death in 1964.
7. Billy Tipton
Billy Tipton was a jazz musician who played piano and saxophone. Born in 1914 as Dorothy Lucille Tipton, she was denied a spot in her high school band because she was a girl. Billy was already a professional musician when she began dressing as a man to better blend in with the other musicians, and by 1940 presented herself as a man both publicly and privately. While playing with various bands, she had long-term relationships with several women who never knew her true sex. Although Billy never legally married, she adopted three sons with stripper Kitty Oakes. Neither Oakes nor their sons knew Tipton's sex until her death in 1989, at age 74.
8. Norah Vincent
Journalist Norah Vincent went undercover for 18 months as Ned Vincent to discover what the world looked like through a man's eyes. The result was the book Self-Made Man, and some insights she didn't expect. You can read an excerpt from the book here.