Originally issued as The Music of Waylon Jennings, this box set is part of a Legacy series that essentially packages four career-spanning discs into a semi-long box package containing 45 tracks with a booklet that features a biographical essay and complete track information. This one divides up easily into three categories, "the singer," "the songwriter," and "the collaborator," and Jennings broke ground in all three areas during his career. "The singer" chapter includes music from his groundbreaking RCA period in which he issued a slew of charting country singles. These tracks include his signature reading of Steve Young's "Lonesome On'ry and Mean," "Stop the World (And Let Me Off)," "The Taker," and "Ain't Living Long Like This." The second section showcases the aspect few people really take into account when regarding Jennings, and that is as a songwriter. Some of these tunes, such as "Are Your Sure Hank Done It This Way?" crossed over onto the pop charts as they connected with rock & roll audiences as well as country fans. Other Jennings' classics here include "I've Always Been Crazy," "This Time," "Waymore's Blues," and of course, "Good Ol' Boys," the theme from the television series Dukes of Hazzard. The third phase covers the collaborations Jennings recorded with RCA and Columbia. There are tracks with the Highwaymen that also included Johnny Cash, Willie Nelson, and Kris Kristofferson. The tracks on this third CD are mostly stone classics, such as his duets with Nelson on "Good Hearted Woman," "Luckenbach, Texas," and "Mammas, Don't Let Your Babies Grow Up to Be Cowboys," and those with his wife, Jessi Colter: the medley of "Wild Side of Life/It Wasn't God Who Made Honky Tonk Angels" and the gorgeous "Storms Never Last." In all, while this isn't a complete portrait of the enigmatic Jennings, it certainly is a well-rounded one.