Greatest Hits (& Some That Will Be) was released in the fall of 1981, summarizing a remarkable seven-year stretch of extraordinary success that began when the iconoclastic Red Headed Stranger, Willie Nelson's first album for Columbia, became a smash hit not long after its 1975 release. From that point on, Nelson became an American popular music icon and a fixture at the top of the country charts, something that was all the more remarkable because he rarely played it safe: he sang pop standards, jammed like the Grateful Dead, recorded tributes to heroes like Lefty Frizzell, and did duet albums with both mentor Ray Price and fellow maverick Leon Russell.

When Willie Nelson took the unexpected step of releasing Stardust in 1978, many predicted that the album of popular standards would severely derail the outlaw country singer's career. Confounding the critics, the disc became Nelson's best-selling effort, and spawned a whole subgenre of modern singers covering the classics. Nelson revisited the format with 1994's orchestral Healing Hands of Time and to varying degrees on several other records, but it wasn't until 2009's American Classic that the red-headed stranger delivered an album billed as the true follow-up to Stardust. Released on the venerable Blue Note label, the disc features guest appearances by superstar jazz singers Norah Jones and Diana Krall, but the focus is always placed squarely on Nelson's famously idiosyncratic vocals…