Initially, he worked in positions of traditional labor, but he obtained the early skills of an entertainer while dancing in the street for nickels and dimes.
Medicine shows were common during that period of American history and they provided many young men with an opportunity to develop more professional skills.
[3][page needed] At the end of Ringling Brothers 1915 season, he joined Ralph Dunbar's Tennessee Ten on the Keith-Proctor circuit.
Upon his return to the United States in 1919, Ulysses visited relatives in Hot Springs, Arkansas, before rejoining the Tennessee Ten for five more seasons, working forty weeks a year.
In 1921, Ulysses married Florence Mills in New York, and in 1922, the couple joined the cast of Noble Sissle and Eubie Blake's Shuffle Along.
The 1930s saw him performing worldwide as a tap dancer in such distant places as Auckland and Wellington, New Zealand; Bucharest, Romania; Budapest, Hungary; Berlin, Germany; Bombay, India; Manila, Philippines; Shanghai and Hong Kong, China; Hawaii; Cuba; and Australia, where he made three tours under the management of George Sorlie.