Before the live recording of "How Lucky" on *The Late Show with Stephen Colbert*, Kurt Vile released the EP *Speed, Sound, Lonely KV* in 2020. This work showcases his signature blend of indie rock and folk influences, highlighting his distinct songwriting style. The choice of performing a cover of John Prine's poignant track, "How Lucky," reflects Vile's reverence for classic Americana and roots music, further indicating his connection to the genre's heritage. At this point in his career, Vile was continuing to expand his discography and collaborate with various artists while solidifying his presence in the contemporary music scene. Additionally, his relaxed demeanor and engaging stage presence during the performance exemplify the laid-back aesthetic that characterizes much of his work. This appearance also underscores Vile's growing visibility, performing on a prominent television platform, which marked a significant moment in his career as an artist.