The singer-songwriter has previously released four full-length albums, including his debut, Shadows, a live record ( Live at the Heartbreak House), a covers EP ( The Madrid Sessions) and the original songs of his most recent effort, On the Shoulders of Giants. James’s reimagining included “adding a depth of sorrow and darkness not just to the lyrics, but the ambience and delivery of the performance,” slowing the song down to emphasize the depth of feeling as he tries to say goodbye. “People can relate on some level or another regarding love, loss, addiction, and the reaction to dealing with those things.” “The emotional heaviness of the lyrics is what drew me to it,” explains James. His aching cover of Macy Gray’s “I Try” for ’s “GRAMMY ReImagined” feature takes the original, a three-time nominee (for both Record and Song of the Year) and winner for Best Female Pop Vocal Performance at the 43rd Annual GRAMMY Awards in 2000 to the church, bringing out the wrenching anguish and yearning at its core.

Take one listen to Shawn James’ music and you can hear his roots in the Mississippi delta by way of growing up on the fabled South Side of Chicago, his authentic, gutbucket blend of blues, folk, and soul music running the gamut of ecstatic joy and painful anguish.