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Cunningham's music is a mix of Folk, Soul, and Rock and Roll. Influenced by artists like Jimi Hendrix, Bob Dylan, Oasis, and The Rolling Stones. Isaiah is a steady songwriter. A former athlete turned musician after his time in college. After that He spent time serving in the U.S. Army. He has played with a number of bands since 2019. Currently he is a singer and lead guitarist of Illinois based rock band 'Isaiah Cunningham & The System'. He has played various shows as a solo acoustic artist as well since 2022. Notably playing shows with 'The Black Opry Revue Tour'.
