Sherman H. Dudley, Black vaudevillian and theater owner, was born in Dallas around 1870. According to various sources he was involved in medicine shows and minstrel groups in his youth. One account reports that his Dudley Georgia Minstrels received a favorable review from the Galveston News in 1897. Most sources place him in P. T. Wright's Nashville Students and in the McCabe and Young Minstrels, where he was nicknamed either Happy or Hapsy.
Dudley wrote a play, The Smart Set, first staged in 1896. In 1904 he appeared with Billy Kersands in King Rastus. Later that year, after Tom McIntosh's death, he took over McIntosh's lead role in The Smart Set. The same year he introduced his most famous stage act, a routine in which a mule dressed in overalls would nod his head as Dudley spoke, giving the impression that the mule understood. According to the obituary for Dudley in the Baltimore Afro-American, this number "never failed to convulse the house." Dudley introduced the mule act in The Black Politician, which he had written with S. B. Cassion. He also contributed material to His Honor, the Barber, produced in 1909–11, and, with Henry Troy, wrote Dr. Beans from Boston, which was staged in 1911–12.
Dudley reportedly organized the Colored Actors' Union, headquartered in Washington, D.C., and served as its general manager and treasurer. In 1911 he began buying theaters and organized S. H. Dudley Theatrical Enterprises. By 1913 this project had developed the first Black theatrical circuit, which, in the beginning, included eight or nine theaters in Washington and Virginia, five or six of which were owned by Dudley. By 1916 more than twenty-eight theaters had joined the Dudley circuit, which extended into the East, South, and Midwest. The circuit enabled Black entertainers for the first time to secure contracts for an eight-month season through one office.
Dudley retired from the stage after 1917 and devoted himself to producing musicals. He regularly updated his Smart Set productions, which continued to be popular with Black audiences. This show was one of a number of musicals written by Blacks in the late nineteenth and early twentieth centuries that departed from the older minstrel show. Dudley was a pioneer in writing works about Black life that included seriously considered plots and rounded characterization.
He was married to the actress Alberta (Bertie) Ormes and was a friend of heavyweight boxing champion Jack Johnson, with whom he was once in business. Dudley sold his theaters after the onset of the Great Depression and retired to his farm in Maryland, where he raised thoroughbred cattle and racehorses. He died there on March 1, 1940, and was buried in Harmony Cemetery. He was survived by a son.