Those whose knowledge of country music history begins with Travis Tritt (or even Hank Williams, Jr.) probably have a hard time understanding what "outlaw country" meant in the late-'60s/early-'70s. Willie Nelson, along with people like Waylon Jennings and Kris Kristofferson pioneered the movement, offering a gritty, rootsy, long-haired, rock-informed alternative to the Billy Sherrill-produced, strings-and-choir-laden Nashville pap that was being pumped out to the country audience. Nelson had already been kicking around for quite a while, penning hits for others (most notably Patsy Cline's "Crazy" and Faron Young's "Hello Walls"), but unable to make a mark as a solo artist. Eventually, he decided to see what would happen if he let his hair down (both figuratively and literally) to appeal to the younger generation. On milestone albums like PHASES AND STAGES and RED HEADED STRANGER, his approach defined "progressive country," retaining a raw, authentic sound without adhering to Nashville strictures.
By the '70s, he had become a unique stylist who owed little to any one genre. His jazzy nylon-string guitar and relaxed croon proved infinitely adaptable. He tackled standards to fine effect on STARDUST and SOMEWHERE OVER THE RAINBOW. By the '80s, he was a pop icon on a par with Sinatra or Streisand, cutting duets with decidedly non-country artists like Julio Iglesias, as well as collaborating with Kristofferson, Jennings and Johnny Cash in the country supergroup the Highwaymen.