Dunbar's parents, Joshua and Matilda, began having marital problems a few months after their son's birth. After the birth of her daughter, who was ignored by Joshua, Matilda took the children, including two from a previous marriage, and left him. Joshua died in 1884 when Dunbar was 12 years old.
Dunbar was the only African-American student during the years he attended Dayton's Central High School, and he participated actively as a student. During high school, he was both the editor of the school newspaper and class president, as well as the president of the school literary society. He wrote his first poem at age 6 and gave his first public recital at age 9. His mother Matilda assisted him in his schooling, having learned how to read expressly for that purpose. She often read the Bible with him and thought he might become a minister for the African Methodist Episcopal Church.
Dunbar's first professionally published poems were "Our Martyred Soldiers" and "On The River", published in Dayton's The Herald newspaper in 1888. In 1890 Dunbar wrote and edited Dayton's first weekly African-American newspaper, The Tattler, printed by the fledgling company of his high school acquaintances Wilbur and Orville Wright. The paper lasted only 6 weeks.
When his formal schooling ended in 1891, Dunbar took a job as an elevator operator, earning a salary of four dollars a week. The next year, Dunbar asked the Wrights to publish his dialect poems in book form, but the brothers did not have the facility to do so. Dunbar was directed to the United Brethren Publishing House which, in 1893, printed Dunbar's first collection of poetry, Oak and Ivy. Dunbar subsidized the printing of the book himself, though he earned back his investment in two weeks by selling copies personally, often to passengers on his elevator. The larger section of the book, the "Oak" section, consisted of traditional verse whereas the smaller section, the "Ivy", featured light poems written in dialect.
The work attracted the attention of James Whitcomb Riley, the popular "Hoosier Poet". Both Riley and Dunbar wrote poems in both standard English and dialect.
Despite frequently publishing poems and occasionally giving public readings, Dunbar had difficulty financially supporting himself and his mother. Many of his efforts were unpaid and he was a reckless spender, leaving him in debt by the mid-1890s.
On June 27, 1896, the novelist, editor, and critic William Dean Howells published a favorable review of Dunbar's second book, Majors and Minors. Howells's influence made Dunbar famous and brought national attention to his writing. Though he saw "honest thinking and true feeling" in Dunbar's traditional poems, he particularly praised Dunbar's dialect poems. With his new-found international literary fame, Dunbar collected his first two books into one volume, Lyrics of Lowly Life, which included an introduction by Howells.
Dunbar maintained a lifelong friendship with the Wrights. He was also associated with Frederick Douglass, Booker T. Waington and Brand Whitlock (who was described as a close friend). He was honored with a ceremonial sword by President Theodore Roosevelt.
Dunbar traveled to England in 1897 to recite his works on the London literary circuit. He met the young black composer Samuel Coleridge-Taylor who set some of his poems to music and who was influenced by Dunbar to use African and American Negro songs and tunes in future compositions. Also living in London at the time, African-American playwright Henry Francis Downing arranged a joint recital for Dunbar and Coleridge-Taylor, under the patronage of John Hay, the American ambassador to Britain. Downing also lodged Dunbar in London while Dunbar worked on his first novel, The Uncalled (1898).