Stephen came to Cincinnati to work as a bookkeeper at the Irwin and Foster Steamboat Company but that didn't last long as his music career started to take off. The city at the time was a sort of cultural melting pot, where Irish, Scottish, African slaves, and river workers intermingled. These influences inspired many of Stephen's songs. During much of the 1850s his music would be disseminated through the touring minstrel shows called Christy Minstrels.
As the Civil War approached, Stephen's songwriting began to slump and his popularity waned, along with his income despite the royalties he earned from music deals. The money he did obtain went mostly to sustain his alcohol addiction. His wife (they married in 1850) and daughter left him prior to the outbreak of the Civil War. Stephen died alone in a flophouse in New York City, addicted to alcohol to the point he sold his own clothes and neglected his health. He cut himself while shaving and died of an infection in January, 1864, in a New York City slum.