Born in Tuscumbia, Alabama, Cooley received his first music lessons at age eight from Al Lester, a Muscle Shoals bluegrass artist who performed with such luminaries as Willie Nelson, Wilson Pickett, Bill Monroe, and Boz Scaggs. Lester even had his own TV show, and it was there that Cooley made some of his first public performances. After getting his first electric guitar, he played a couple of gigs with high school friends before taking a break from music making. Eventually, in 1985, he formed the post-punk act Adam's House Cat with Hood, his then roommate. Once the group disbanded they occasionally worked together as a duo under the moniker Virgil Kane, named after the main character in the Band's 1969 track, "The Night They Drove Old Dixie Down." Their next band, Horsepussy, was formed when the pair resided in Auburn, Alabama, but this was also a short-lived affair.
After Hood had spent some time in Athens, Georgia, he eventually persuaded Cooley to join him, and it was there that they formed Drive-By Truckers in 1996. Cooley contributed six songs to their career highlight, 2014's English Oceans, and by the end of 2020 they had recorded 13 studio albums and garnered a reputation as a raucous, hard-working live act. Along the way, Cooley issued a pared-down, live solo acoustic set, 2012's The Fool on Every Corner. Recorded at The Earl in Atlanta, it showcased his narrative songwriting and accomplished fingerpicking technique on revamped versions of Cooley's compositions from the Drive-By Truckers' canon. Although Cooley and Hood would sporadically perform as the live acoustic duo the Dimmer Twins, Cooley's place in Drive-By Truckers continued to be his main musical outlet. However, in 2021, an expansive, seven-year-old performance was issued as Live at The Shoals Theatre, June 15th, 2014, billing Cooley alongside Hood and former Drive-By Trucker-turned-solo artist Jason Isbell. ~ James Wilkinson, Rovi