He gained notability in the late nineteenth and early twentieth century as an individual performer, a composer of ragtime songs, and as a member and later owner of various minstrel shows including the Smart Set Company.

By 1897 he had his own show, the "S. H. Dudley's Georgia Minstrels", who were performing in Galveston; later that same year he was on tour with P. T. Wright's Nashville Students Company.

He gained a reputation for writing popular coon songs (including a hit song called "Mr. Coon, You'se Too Black For Me"),[4] and performed with a number of minstrel comedians in shows in the same vein, including A Holiday in Coonville (his own production) and Coontown Golf Club (a production by Tom Brown[5] and Sam Cousins[6]).

[7] When he toured with Tom Brown and Billy Kersands in 1902, it was clear that he was a popular, well-known artist in the South, and was billed as "the Lone-Star comedian".

[12] In 1909, the Smart Set split up in a Northern and a Southern Smart Set, the first being directed by Dudley and the latter by his understudy, Salem Tutt Whitney; their 1909–10 production, His Honor, the Barber was written by a white playwright, Edwin Handford, with music written for the show by black composers James Tim Brymn, Chris Smith, and James Burris.

[13] By this time, Dudley was widely known as the "Lone Star Comedian" and had begun to expand his business ventures, moving into theater in an attempt to have a black-owned and operated string of venues around the United States, a dream of his since at least 1907.