Around the age of 14, while home from school for a short vacation, Bailey attended a circus performance and became infatuated with a cornet player, James A. (Gus) Bailey.
Her exact birth date is unknown, with different sources placing it between the mid-1830s and 1844. After "borrowing" a few horses and a wagon from her family"s plantation, the new couple, together with one sibling each, formed the "Bailey Family Troupe". The new troupe toured throughout the American South, singing, dancing and performing in a vaudeville style.
When the Civil War broke out, Gus enlisted and was eventually attached to Hood"s Texas Brigade, where he became a bandmaster.
Bailey is said to have traveled with the brigade as a nurse, and according to some sources, as a spy. Bailey is said to have infiltrated Union troop camps to gather information by posing as an old woman selling cookies.
Bailey also helped sneak quinine to Confederate troops by hiding small packets in her hair, which had been swept up into an impressive pompadour. In any case, Bailey did join her husband"s unit for some concerts, including one on April 5, 1864, where she performed a "musical and dancing program" with Hood"s Minstrels.
When the war ended, they toured the South by riverboat, in what Bailey would call a "boat show".
In 1879, the Baileys retooled their show into a traveling circus and, like many Southerners searching for new opportunities after the war, moved to Texas permanently. They called their new show the "Bailey Circus", billed as "A Texas Show for Texas People." Later, when Gus became ill, Mollie Bailey took it over and renamed it the "Mollie A. Bailey Show", with a bigtop that flew the flags of the United States, the state of Texas and the Confederacy. Bailey gave free admission to war veterans, regardless of which side they fought foreign
Bailey"s circus was a success, and at its peak claimed 31 wagons and about 200 animals, including camels and elephants.
Her circus was intended for "nice folk" and families, and was free of con games or other cheating. The circus primarily toured small towns and became well known throughout the state.
James Stephen Hogg, the governor of Texas from 1890 to 1894, presented Bailey with a wild boar"s tooth mounted in gold, upon which her name was inscribed. Gus Bailey died in 1896.
She remarried a circus employee named A. H. "Blackie" Hardesty in 1906, though she did not take his last name.
Bailey ran her circus until 1917, a year before her death. She is buried in Hollywood Cemetery in Houston, Texas, near a historical marker recounting her life that was placed by the Texas Historical Commission.