During the middle of recording his debut album The Road, John John Brown fell down a 75 foot well and luckily his acoustic guitar broke his fall. He was literally saved by music. Although much of the "The Road" is still in the vault, Brown's live acoustic performances of the album have been garnering much critical acclaim. In May of 2015 he was chosen as a Kerrville Folk Finalist for the legendary “New Folk" competition, and in January of 2016 he went home a winner of the prestigious South Florida Folk Festival Songwriting Contest. Seeped in good storytelling and fingerpicking melodies, John John Brown seems to have discovered part of the mystery that surrounds the great singer/songwriter tradition. "The Road" was released in the summer of 2016.

No Depression calls John John Brown’s debut album The Road, "A supple and suggestive blend of astute Americana accompanied by a quiet, reflective glow". He’s been selected as a Kerrville New Folk Winner Folk in 2020 and as a 2017 Emerging Artist at the Falcon Ridge Folk Festival. In 2019, he played the 50th Anniversary of Woodstock at Bethel Woods. Brown's sophomore album Americana Comics, a collection of storytelling songs he had drawn up as comic books, is set to be released on January 10, 2021. It is heavily influenced by the songwriting of John Prine.