In March 1887 he was given a juvenile role in Smokey Moke at a local variety beer hall called Streakbiner's Garden.

He played for some years in St. Joseph and Kansas City, then found work in Denver and the surrounding mining towns, where he first met Fred Stone.

[2] While in Denver Montgomery was offered a job with the J. H. Haverly’s minstrel company, which was planning to first tour the southern USA and then move to New York.

[5] Montgomery was able to find a two-week engagement at a local variety theatre for himself and Stone, then got an offer from Billy Rice for them to appear in a minstrel show in Chicago at Hall's Casino.

Montgomery and Stone were hired to perform in the Casino, Lyceum and Hopkins theaters in Chicago from March to June, and became well known for their original dance routine.

[5] After spending the summer in Chicago the two took the train to Boston, where they opened in Gus Hill's Novelties on September 19, 1896, at Keith's Theater.

[6] The tour with Gus Fields took them to Newark, Washington, Baltimore, Pittsburgh, Indianapolis, Cincinnati, St. Louis, Kansas City and to Chicago's Haymarket Theatre for Christmas.

[7] They continued with Hill's company, via Cleveland, Buffalo, Rochester and Syracuse to reach New York City at the beginning of February 1897.

[8] A review of the show said "Montgomery and Stone, in blackface, gave excellent imitations of real politicians, the hobby of the day, and by their singing and quaint expressions, as well as their startling moves, kept the audience laughing and applauding.

Montgomery and Stone were hired by Gustav Walter to play in his Orpheum Circuit theaters on west coast, starting in San Francisco on March 5.

[12] Montgomery and Stone returned to the West coast in January 1899, playing in California until April 1899, and had a series of theatre engagements in St. Louis, Chicago, New York and Buffalo before leaving for England.

This may be the same song as Hurrah for Baffin's Bay, one of the hits from The Wizard of Oz, with music by Theodore F. Morse and words by Vincent Bryan.

[17] They played the roles of Con Kidder and Kid Conner, two penniless American vaudevillians stranded at a small inn in Holland.

[19] Montgomery and Stone often performed in vaudeville tours between Broadway engagements where they appeared in The Old Town (1909), The Lady of the Slipper (1912) and Chin-Chin (1914).

Stone have been inseparably linked with fun and frolic ever since years ago they forsook vaudeville to enter the musical comedy field, and the same applies to Miss Janis, and in their present vehicle they live up to their reputations to the utmost degree.