Baby Esther lived in the "colored" neighborhood of Chicago with her mother and father. Esther's career began in the 1920s when she won first prize at a Charleston contest in Chicago at the age of six. Russian-American theatrical manager Lou Bolton saw her performance and took her on, with her first performance purportedly being in a Chicago revue, Opera Versus Charleston. Bolton went on to arrange engagements for Esther in Chicago, New York, Detroit, Toronto and other cities, after which he brought her to Europe. Esther Jones was rarely called Baby Esther while performing, most commonly going by the names "Li'l Esther" and "Little Esther." Originally she was billed "Farina's Kid Sister," but was later known as the "Miniature Florence Mills", as Esther had started her career impersonating Florence Mills. Florence Mills was noted for her "light, bright" voice and her use of wordless vocalizations such as "too-ty-tooty-too". The name "Farina's Kid Sister" derived from Allen "Farina" Hoskins, another African-American child star of the period. Apart from his ongoing role in Our Gang comedies, Hoskins was an expert Charleston dancer, performing along with his sister "Baby Jane." Lou Bolton, Esther's first manager, used Hoskins' fame to promote Esther in the early years of her career; the name formulation of Little (or Lil'/Li'l) Esther mimicked Hoskins' "Little Farina," a frequently-used nickname. While touring Spain, Esther was referenced as a member of "La Pandilla," the Spanish name for the Our Gang kids (taken from their alternate series name of "Hal Roach's Rascals"); at least once, she was specifically tagged as the performer of Farina, due to her past imitations of him. 1928 Esther performed briefly at a nightclub called the Everglades Club, where she would do imitations of Florence Mills, late at night. In June, Esther's father William Jones and manager Lou Bolton was charged for having a minor perform on stage; one write-up of the incident suggested that William Jones was not Esther's birth parent. In late 1928 Esther was signed for a talking short by Movietone, booked through William Morris for MGM. While the short was later listed variously as being in production or completed, it has not surfaced as of 2020. Harrison G. Smith, a business associate of Bolden Smith of New York, furnished Esther with several songs: "The Turtle Walk," "My Little Dixie Home," "I've Got the Blues for Dixieland," and "I Need a Man (Around My House)."