Bob Cole was recognized as a leader in musical theater in his day. Born in Athens, Georgia, he attended public schools and eventually moved northeast to Chicago. In Chicago he produced vaudeville acts before he went solo, as a comic. In the mid-1890s, Cole moved to Manhattan where he worked in Sam Lucas's Creole Show as a comedian and stage manager. Cole joined the mysterious All-Star Stock Company, a group of New York performers which included Gussie Davis, Ben Hunn, Billy Johnson, Stella Wiley, Hen Wise, and Will Marion Cook. The group met as a collective to discuss their artistic and personal needs and produced two known plays: Georgia 49 and A Pair of Spectacles. The group soon disbanded, and its members pursued individual careers.

Through the All-Star Stock Company Cole partnered with Billy Johnson. Cole and Johnson produced Jolly Coon-ey Island for Black Patti's Troubadours, but conflict with the troupe's white management prevented the show from opening. The management of Black Patti's Troubadours initiated a boycott of the duo's next show, A Trip to Coontown, which was set to premier in 1897. The boycott forced A Trip to Coontown to play the worst theaters in Canada and various American cities before eventually premiering in New York in the fall of 1898. It was the first full-length musical to be written, produced, and managed by black musicians, and starred an all-black cast. It ran until 1900, after which Cole split with Billy Johnson over financial disputes.³⁴

A Trip to Coontown was not merely a Broadway "first". Cole and other black musicians perceived A Trip to Coontown as an entrée into creative and political freedom. Bob Cole's 1898 Colored Actor's Declaration of Independence, boasted: "we are going to have our own shows. We are going to write them ourselves, we are going to have our own stage manager, our own orchestra leader and our own manager out front to count up. No divided houses—our race must be seated from the boxes back."³⁵

In 1901 Bob Cole teamed with James Weldon Johnson and J. Rosamond Johnson. The team signed a three year contract with publisher Joseph W. Stern and Company. They received guaranteed monthly payments for their songs, to be deducted from their royalties. This was the first such contract ever made between black song writers and a Tin Pan Alley publisher³⁶. On November 1st, 1902, the Colored American celebrated the collaboration: "their primary ambition is to develop a distinct school of music from the primitive melodies of our race and to do for Negro music in this country what Coleridge Taylor is doing for it in England.³⁷" Cole and the Johnsons produced The Shoo Fly Regiment, which premiered on Broadway in 1907 and The Red Moon, which premiered at The Majestic Theater on Broadway in 1908 to great critical acclaim. At the end of the 1909/1910 theater season Bob Cole announced his retirement from musical comedy, and returned to vaudeville with J. Rosamond Johnson, earning $750 per week. Tragically, at the height of his genius he suffered a mental breakdown, which worsened throughout 1910. He committed suicide in 1911, devastating the theater community, especially his good friends and colleagues J. Rosamond and James Weldon Johnson. James Weldon Johnson recalled the impact of Cole's death years later in his autobiography:

I was shocked and disturbed beyond measure. I had lost one of the closest friends of my lifetime, a friend whom I loved not only for his unchanging fidelity, but whom I admired for his unquestionable genius. I thought back over the twelve years of our relations; I again lived through experiences that we had suffered or enjoyed together; I tried to reckon the degree of his influence on the course my life had taken; and I felt only deep contentment in the fact that we had been friends and co-workers. Bob Cole's death was a vital loss to the Negro stage.³⁸

Famed for his talents as an all-around performer, composer, director, producer, and scenarist, he was recognized in his time as an indisputable leader in black music and black theater by his contemporaries. The Cole and Johnson Brothers compositions were stock songs for both white and black theater productions, and Cole transformed the direction of black musical theater by demanding that representations of blacks in his songs and musicals diverged from the minstrel caricatures that were so ubiquitous. As James Weldon Johnson put it, "Cole was the most versatile man in the group and a true artist. In everything he did he strove for the fine artistic effect, regardless of whether it had any direct relation to the Negro or not. Nevertheless, there was an element of pro-Negro propaganda in all his efforts;"³⁹