Hailing from Holt, Missouri, Riley Downing grew up in a family of country and bluegrass fans, while his grandmother's uncles played old-timey music. While he would grow to love and respect roots music, in high school, he was more interested in punk and straight-ahead rock & roll; he got a guitar when he was 14, and was soon playing with local bands. (He claims to have made his first album with one of his high school bands when he was 15, though he prefers not to share the details.) When he was 18, he traveled to Kansas and attended the Winfield Bluegrass Festival, and he quickly became a convert to acoustic music. Downing steeped himself in bluegrass, folk, and blues music, and while attending the Woody Guthrie Folk Festival in Okemah, Oklahoma, he met Sam Doores and Cameron Snyder, like-minded musicians who played in a group called the Broken Wing Routine. When Broken Wing Routine broke up, Doores and Snyder relocated to New Orleans, and invited Downing to join them in a new Americana band they were putting together. Originally called the Tumbleweeds, the act soon evolved into the Deslondes, who cut their critically acclaimed first album in 2015.
Following the touring cycle for the second Deslondes album, 2017's Hurry Home, Downing headed back to Missouri to relax and spend time with family. He played a few solo shows, and while biding his time during the Covid-19 lockdown period in 2020, he began blocking out plans to cut a solo single with his Deslondes bandmate John James Tourville, who was staying in North Carolina. Andrija Tokic, a Nashville-based producer and engineer who had worked with the Deslondes, also became involved in the project, and as the three traded ideas and music files back and forth, Downing's stack of new songs began to grow. By the time Downing and Tourville were finally able to meet up in person at Tokic's Nashville studio, they had enough material for an album, and Tokic put together a band of studio musicians that included folks who had played with Vince Gill, George Strait, Dolly Parton, Bob Dylan, John Prine, and other country and roots music heroes. The sessions produced Downing's first solo album, Start It Over, released by New West Records in 2021. ~ Mark Deming, Rovi