Bess Rudisill was born in Rensselaer, Ralls County, Missouri, around 100 miles from the area considered to be the "Cradle of Ragtime." She was the second of four children born to James W. Rudisill and Ella M. Bradley, including one older sister, Mina (12/1882), and two younger brothers, Homer Corwin (3/26/1891) and Robert Alva (8/16/1896). Soon after she was born the family moved to the nearby New London, Missouri, area. At the time of her birth James Rudisill was a farmer. However, the 1900 census shows James to be a drug store clerk and Ella as a dressmaker, the family having moved once again, this time west to Spencer in the same area of Missouri. Bess was still in school at that time.

According to information uncovered by historian Nora Hulse, the family as a whole was rather musical. One clipping describing a local contest for the best musical family talked about James as the violinist, Ella as the cellist, Mina on the less than musical comb, and Bess at the piano. After playing "some soul stirring selections" they took the prize for the contest. James also had his own small string group for which Bess accompanied for dances, starting as young as 14 years. She was also elected the organist for a local group of young Baptists. Her inherent musicality was rewarded in 1900 when the citizens of New London sponsored a musical and literary program at the local Opera House, with the proceeds going to procure a piano for the talented teen. That same summer the family moved to St. Louis to afford their daughter the opportunity to work in the music department of the elegant Crawford's Department Store. (The beautiful original building still exists in downtown St. Louis.)

As for composing, Bess had already started writing her own tunes by age 11. So it was not long after the family relocation that she got her first piece into print, Francis Two Step, which was dedicated to D.R. Francis, president of the company that was working on the upcoming Lewis and Clark Louisiana Purchase Exposition, or World's Fair. It was soon followed by Polka Dot: March and Two Step, published first in Saint Louis, then later bought and reissued by Harold Rossiter in Chicago. As an encore to that Bess came up with Way Down East which was ultimately released in two editions with varying covers. It was dedicated to Pattie Buchanan of Billings, Montana, cited as her teacher. Given the time line, it seems more likely that Miss Buchanan was either from or had perhaps relocated to Billings, rather than Bess or the family having ventured that far from Missouri. Many of her earlier works were issued by Saint Louis printer Samuel Simon, but some were later bought up by larger publishing houses such as Rossiter's.

Yet another raggy march, Bright Eyes, appeared the following year. Around that time she was working for the Famous department store at Broadway and Morgan as their music demonstrator. Her first true piano rag, Burning Rags, made it into print around the time of the the World's Fair in 1904. In addition, with local lyricist Eddie Dustin, she composed I'll Meet You on the Pike, one of many pieces that was associated with the famous mile-long amusement pike, a feature of the exposition. Bess found even more notoriety the following year. As recounted in the April 29, 1905 edition of The Music Trade Review:

It is unclear if Miss Rudisill lived in Chicago at any point between 1904 and 1908, but she may have at least spent some time there as most of her works were published in that city, at least a half-day train ride from St. Louis. It was more likely a business arrangement while she continued to work in St. Louis, possibly even representing Whitney-Warner and Remick as part of her job. In 1910 Bess was shown in the census as residing in St. Louis with her parents, with James now working as a "park keeper" for the city, and Bess clearly still working as a pianist for one of the local department stores. Mina and her new husband George P. Agnew were also living in the Rudisill household.

There is some mystery as to when and how Bess met Detroit, Michigan, lumberman Earl Jackson Leech, although he did some sales travel for the Stewart Greer Lumber Company of St. Louis. On October 19, 1911, Earl and Bess were married in Detroit. She may have played in the motor city now and then, and perhaps even worked for the local Jerome H. Remick publishing office, but confirmation of her Detroit activities was difficult to find. Her final published composition, The Eight O'Clock Rush, was put into print in Chicago in two different arrangements of varying difficulty shortly after her wedding. The title likely reflects a street scene between the time of dinner and when the theater shows got underway in the city.

Earl appears to be single again in Detroit directories of 1913 and later, so it is apparent that the marriage did not last long. Bessie then opted for a run on stage as a member of the vaudeville circuit for one of the many large touring companies during the 1910s, most likely as an accompanist. She was found in Oklahoma City for the January 1920 enumeration as Bessie Rudisill, listed as divorced and working as a vaudeville musician lodging with a number of other members of the troupe, and for whatever reason having deflated her age from 35 to 29.

In 1922 Bess relocated to the West Coast, living in the Los Angeles area for the remainder of her life with her brother Robert. She became a fixture on Los Angeles radio in 1924 on station KHJ as part of the Studebaker Radio Orchestra, a small jazz ensemble. Bess was also shown as a member of the Southern California Music Company. In a Los Angeles Times review March 15, 1924, the orchestra, headed by violinist Charles H. Lindsay, was said to consist of:

For the 1930 enumeration Bess and Robert were shown as residing in Long Beach, California. He was also an orchestra musician, and she was now listed as an organist, likely working in both theaters and churches, something she appears to have continued doing for most of her final years. The Rudisills were living on Shrine Place in 1940 for the census, with Bess listed as a theater organist, and with a lodger, Betty Hodges, listed as a "partner." Nothing more was found on her, so their relationship is unclear.

Bessie appeared in Los Angeles County voter records with Robert at various addresses through 1954, both listed as musicians in 1942 and 1944, after which time occupations were no longer included. The 1950 census confirmed that Bess no longer engaged in music as an occupation, and that Robert was now a maintenance worker for the Shrine auditorium in Los Angeles. Bess Rudisill finally beat the Eight O'Clock Rush, leaving it behind at age 72 in Los Angeles, apparently having never married again.