[1][2] Hilliard was born in New York City in 1857, and got involved in acting through amateur productions while he was working as a clerk on Wall Street.

The Oxford Companion to American Theatre states that "although he was a star for many years, most of the plays in which he acted were popular but ephemeral works."

[2] As his nickname "Handsome Bob" might indicate, Hilliard was known for his attractive looks and for being very well-dressed in the fashions of the day.

By 1888, Hilliard was set up as a foil by the press to Evander Berry Wall as to who should be called "King of the Dudes".

[3] Hilliard died of heart disease at his home on West 58th Street in Manhattan on June 6, 1927, and was buried at Green-Wood Cemetery.