Waylon Jennings

Somebody once joked that outlaw country was invented in the early ’70s just so country singers could get laid by hippie chicks, but after the snickering was over, it couldn’t be denied that this mix of honky-tonk country and rock attitude had made an impact. It would have happened anyway (other artists hit on the idea of “progressive country” around the same time), but Waylon Jennings epitomized the scene.

This four-CD boxed set and separately sold companion DVD chronicle Jennings’s progression from his pop-country beginnings to the long-haired, system-fighting honky-tonk rocker we all came to know. Both find their grooves during Jennings’s 1970–74 era, as he was just starting to hit his stride, easing away from the Nashville factory and recording unconventional songs by hip, young songwriters like Billy Joe Shaver and Kris Kristofferson. His mainstream years (1958–69) are heard on disc one of the set, and Jennings would have remained a footnote in country history if that were all he did. (He didn’t always get the best material, either: His pal Willie Nelson redoes “Yours Love” on his own new album—and it stinks even now.) Fortunately, the best songs from that period are weeded out. The quality slows down mightily by disc four (we’d love to say that Jennings rebounded in the ’80s and ’90s after a short period of media overkill, but it wasn’t so). By contrast, the DVD focuses on his ’70s heyday, with various TV guest shots and concerts of Jennings totally killing it with his road band—what he was always best at doing.—James Porter