Crossover success usually requires certain concessions, such as shortening songs or collaborating with big-shot producers. Waylon Jennings enhanced his country standing and found a rock audience by doing exactly the opposite. The first disc of this chronological boxed set covers 1958-69, when Jennings worked with Nashville Sound overseer Chet Atkins. The 1970-74 disc contains his mission statement, "Lonesome On'ry and Mean," which Jennings produced himself, with his touring band, the Waylords, backing him in the studio. On the 1974-80 disc, several songs feel abridged, as if Jennings knew they'd continue indefinitely if he didn't fade them midjam. Disc four (1980-95) suffers from a keyboard glaze that recalls late-era Stevie Wonder, but it includes two stellar collaborations: one with Hank Williams Jr. and another with the Highwaymen posse Johnny Cash, Willie Nelson and Kris Kristofferson.
Jennings' material might not have been as categorically solid under his own watch, but confrontational, personal numbers such as "Are You Sure Hank Done It This Way" couldn't have emerged from the factory system. This Nashville rebel preferred occasional mistakes to oppressive, interchangeable competence.