When you think of the classic “top 10 men” list, you probably picture celebrated warriors, explorers, and pioneers. Yet history hides a handful of astonishing figures who performed daring deeds while keeping a secret: they were women masquerading as men. This collection spotlights ten such trailblazers whose remarkable achievements rewrote the rules of their eras.
What Makes These Top 10 Men So Extraordinary
10 Deborah Sampson
Deborah Sampson entered the world in Plympton, Massachusetts, in 1760, born into a respected family but soon thrust into indentured service by the tender age of ten. After fulfilling that obligation, she taught school and earned a living as a weaver, relying on her own education and determination.
In 1782 she slipped into the Fourth Massachusetts Regiment under the alias Robert Shurtleff, joining a Light Infantry company as a scout. During her service she led a squad of thirty infantrymen into battle, captured fifteen enemy soldiers, and helped dig trenches at the pivotal siege of Yorktown.
For nearly two years Sampson guarded her true sex, even extracting a musket ball from her thigh to avoid a medical examination. An infection eventually knocked her unconscious, revealing her secret. She received an honorable discharge and returned home, where she married, raised three children, and settled back into civilian life.
Massachusetts awarded her a military pension, making her the sole woman to receive such a benefit for Revolutionary War service. After her death, her widower petitioned the state to continue the pension, and the legislature granted it, noting her unparalleled example of female heroism, fidelity, and courage.
9 Christian “Kit” Cavanaugh
Born Christian Davies in Ireland in 1667, she inherited a bustling pub from her aunt before marrying Wichard Welsh and bearing two children. While pregnant with a third, a letter arrived announcing her husband’s conscription into the British Army, prompting her to take drastic action.
She entrusted her children to her mother, cut her hair, and assumed the male identity Christopher Welch. By 1693 she had enlisted, fighting at the Battle of Landen, where she was wounded, captured, and later exchanged—all while her disguise remained intact.
After a duel that ended in another soldier’s death, she was discharged but promptly reenlisted with the 2nd Royal North British Dragoons. Her continued service saw her through numerous campaigns until a battlefield injury finally exposed her gender.
When her secret emerged, her commander reunited her with her husband after a thirteen‑year separation. She earned a pension, remained affectionately known as “Mother Ross” by her comrades, and upon her 1739 death was honored with full military rites.
8 Hannah Snell
Hannah Snell grew up in Worcester, England, later marrying and moving to London where she gave birth to a daughter. After her husband abandoned her during pregnancy and the child’s subsequent death, she stole her brother‑in‑law’s clothes, adopting the name James Gray.
Learning that her husband had been executed for murder, she enlisted in the 6th Regiment of Foot under the Duke of Cumberland, then quickly deserted to join the Royal Marines in Portsmouth. In June 1749 she endured eleven wounds, one striking her groin, which she concealed by having a local woman extract the bullet.
The following year she confessed her sex to shipmates and petitioned the Duke for a pension, which he granted—and later increased. Her story was published in The Female Soldier, and she capitalized on it by staging a theatrical version of her exploits.
She retired to East London, opened a tavern called The Widow in Masquerade, remarried twice, raised two more children, and passed away in 1792 at the age of sixty‑nine.
7 Jeanne Louise Antonini
Orphaned by ten, Jeanne Louise Antonini slipped aboard the French frigate La Cornélie disguised as a boy, committing a decade to naval life before a wound in the Napoleonic Wars forced her into captivity.
After eighteen months as a prisoner of war, a peace treaty secured her release. She returned to France, enlisted in the French Army, and continued her male façade, rising to the rank of sergeant over fifteen years of service.
Throughout her military career she sustained numerous injuries, the final blow—a severe head wound during the occupation of Portugal—ending her service. Remarkably, her gender remained undisclosed throughout her 25‑plus years in uniform.
Post‑military, she worked in a brick factory. At seventy, she received the Saint Helena Medal, the first French campaign medal instituted by Napoleon I, and a street in Nantes now bears her name.
6 Charlotte D. Parkhurst
Charlotte D. Parkhurst entered the world in Vermont in 1812, losing both parents and a brother early on. Placed in an orphanage, she remained there until age twelve, when she fled and adopted the name Charley.
Under the mentorship of Ebenezer Balch in Rhode Island, Charley learned the demanding trade of stagecoach driving. By thirty, he journeyed west to California during the Gold Rush, where a horse’s kick to the head cost him an eye.
Undeterred, the one‑eyed Charley rose to fame as a top‑tier driver, navigating treacherous routes plagued by bandits, poor roads, and harsh weather. He earned the moniker “boss of the road” for his daring exploits and professionalism hauling gold between San Hose, San Juan, and Santa Cruz.
After a long, celebrated career, Charley retired and died in 1879 at sixty‑seven. It was only in death that his true sex was uncovered, revealing a lifetime lived under a male guise.
5 Marina The Monk
Marina was born into a wealthy Christian family in the 5th century. Following her mother’s death, her father raised her devoutly and arranged an intended marriage, which she rejected in favor of becoming a monk.
She shaved her head, swapped to men’s attire, and entered a monastery in the Kadisha Valley alongside her father, who became a monk named Eugenius. Adopting the name Marinos, she was accepted as a brother by the community.
Accused of impregnating an innkeeper’s daughter, she was expelled and lived as a beggar. After the child’s birth, she cared for the infant, and years later she was permitted to return to the monastery.
At forty, Marina fell ill and died. When her body was prepared for burial, monks discovered she was a woman, prompting the abbot to lament his unjust punishment. Today, Marina is venerated as a saint across Eastern Orthodox, Catholic, and Coptic traditions.
4 Anna Maria Lane
Anna Maria Lane wed John Lane around the 1776 Declaration of Independence. Rather than remain a camp follower, she disguised herself as a man and enlisted alongside her husband, serving under General Israel Putnam.
The couple fought in campaigns across New York, Pennsylvania, New Jersey, and Georgia, eventually joining General George Washington’s forces at the 1777 Battle of Germantown.
During that battle Anna Maria suffered a severe wound but refused treatment to keep her gender hidden, resulting in a lifelong disability. Nevertheless, she continued to serve beside her husband until 1781, and by 1783 they settled in Virginia.
She received a military pension for her service despite her sex. Governor William H. Cabell specifically noted her condition, describing her as “very infirm, having been disabled by a severe wound which she received while fighting as a common soldier.”
3 Dorothy Lawrence
Dorothy Lawrence dreamed of journalism and succeeded in publishing articles in early‑20th‑century newspapers. When World War I erupted, she sought to become a war correspondent but was barred from official accreditation.
Undeterred, she arranged for British soldiers to smuggle her a uniform piece by piece, creating a male persona that allowed her to reach the front lines as a sapper with the 179 Tunneling Company of the Royal Engineers.
Fearing discovery, she confessed her true sex after a near‑miss injury, leading to her arrest and interrogation on espionage suspicions. Ultimately she was released, though the experience left lasting scars.
She authored Sapper Dorothy Lawrence: The Only English Woman Soldier, but the book failed to attract an audience. The emotional toll led to her institutionalization in a London asylum, where she remained until her death in 1964.
2 Billy Tipton
Billy Tipton rose to fame as a celebrated jazz musician and bandleader, thriving from the 1930s through the 1950s and later working as a talent broker until arthritis forced retirement in the 1970s.
When he died in 1989 at seventy‑four, family and friends were shocked to learn his birth name was Dorothy Lucille Tipton, born in Oklahoma City in 1914 and raised by an aunt in Kansas City, Missouri.
At nineteen, Dorothy began binding her breasts and adopting male attire to blend into the male‑dominated jazz world. She assumed the name Billy Lee Tipton, fully embracing a male identity throughout her career and personal life.
Upon his death, Billy’s adopted son William discovered the truth, a revelation that shocked everyone, including the women who had shared intimate relationships with him.
1 Dr. James Berry
James Berry entered the world in 1789, initially pursuing a teaching career before turning to medicine at the University of Edinburgh. After completing his studies, he moved to London to refine his surgical techniques.
Commissioned into the British Army in 1813, Berry rose to Inspector General, overseeing numerous military hospitals. Among his achievements was performing Europe’s first successful cesarean section in Africa.
Berry’s remarkable medical career continued unnoticed until after his death, when a post‑mortem revealed he was born Margaret Ann Bulkley. He had lived his entire adult life as a man to practice medicine.
Rumors swirled for years, but only later did analysis of letters confirm Margaret and James were the same person. Her decision to masquerade as a man enabled her to attend medical school and serve as a physician.