Some of the legends of outlaw country did real jail time, but the term comes not from literal criminality but from breaking musical norms, a rebellion against the mainstream country of the era (grunge would play a similar role in the 90s). The stripped-down sound signifies something real, but it also allowed singers like Willie Nelson and Merle Haggard to get weird, their eccentricities clear and unvarnished. You better make it to the end and listen to the live acoustic version of Townes Van Zandt’s “Pancho and Lefty,” a genuinely perfect song.