Henry Starr was born near Fort Gibson in Indian Territory on December 2, 1873 to George "Hop” Starr, a half-breed Cherokee, and Mary Scot Starr, a woman of Irish decent and one-quarter Cherokee.  Mary came from an educated and respectable family, but the Starr side of the family was rife with outlaws.  Henry’s grandfather was Tom Starr, an outlaw in his own right.  Henry would later say that his grandfather "was known far and wide as the Devil’s own. In all matters where law and order was on one side, Tom Starr was on the other.”

His uncle was the notorious Sam Starr who was married to Belle Starr, the "Outlaw Queen.”   Belle Starr was widely known for her relationship with the notorious Younger Gang and her criminal escapades through Oklahoma. Henry though, reportedly was not fond of Belle, finding her to be crude and reprehensible, quickly informing anyone who commented on the relationship, that she was his aunt by marriage only.

During the time of Starr’s youth, the northeastern corner of Indian Territory was rugged and untamed, often referred to as the "Land of the Six-Gun” and the "Robbers’ Roost.”  The rough terrain of the area provided a number of natural hideouts for thieves, murderers, and other outlaws seeking refuge from the law. 

In 1886, Henry’s father died leaving Mary to care for three children and the family farm.  However, within just a few months she remarried a man by the name of C.N. Walker, who Henry hated.  Starr felt that Walker was inferior because his veins contained no Indian blood.  Walker was also abusive and he and Henry had immediate problems.  Within just a few short months of his mother’s remarriage Henry left home.

By the age of sixteen, while Henry was working on a ranch near Nowata, in Indian Territory, he had his first run-in with the law.   As Henry was driving a wagon to town two deputy marshals caught him with whiskey and arrested him for "introducing spirits into territory."  Though he plead guilty to the offense, he maintained that he was innocent, having borrowed the wagon without knowing that the whiskey was in it.

Starr returned to Nowata and continued to work as a cowboy, but it wasn’t long before he had another run-in with the law.  In December 1891, he was arrested for stealing a horse, again he denied the charge, but was locked up at Fort Smith, Arkansas anyway.  His cousin paid his bail and Starr hit the road, with a warrant for his arrest hanging over his head. After jumping bail, Henry had made a conscious choice to live on the wrong side of the law.  The warrant for Starr’s arrest was given to Deputy Marshals Henry C. Dickey and Floyd Wilson who were quickly on Henry’s tail.