Waylon is best remembered for the cover of Chuck Berry's "Brown Eyed Handsome Man," which climbed to #3 on the Billboard country charts, Jennings third Top 5 solo hit. Jennings would perform the song as part of a medley on The Johnny Cash Show. Aside from "Brown-Eyed Handsome Man", none of the other songs on this LP were released as singles. The version of "Yes, Virginia" presented here is different from the one originally issued on The One and Only in 1967. According to Waylon's autobiography, the song "Yellow Haired Woman" was written about Barbara Rood, his third wife. Waylon is also significant for its version of "The Thirty-Third of August," written by Texas songwriter Mickey Newbury, a key figure among a new generation of country songwriters that would contribute to the outlaw country movement in country music, of which Jennings would be a central focus. As Tom Jurek observes in his AllMusic review of the album:
"This self-titled album signifies the real beginning of Waylon Jennings' discontent with his career. He is making efforts in the studio here to stretch its boundaries and include material very foreign to Nashville...But it's with Mickey Newbury's "33rd of August" that the pokiness of Waylon's mission becomes apparent. In the slow dirge, complete with gorgeous layers and textures of strings, aberrant percussion, and backing vocals that whisper rather than chorus, Jennings offers another dimension to not only this sad story, but the direction of his musical muse, somewhere in the groove but outside the confines of the studio."
Despite chart success, Jennings had grown frustrated with the Nashville Sound that had been imposed on his records by RCA Victor and especially resented being told what to record. As Joe Nick Patoski notes in his memoir Willie Nelson, "In addition to doing more and more of the songs he wanted to do rather than what the producer chose, Waylon wanted to produce himself and was demanding control of where the records were made, the song selection, and the artwork that decorated the album cover." Relations between Jennings and RCA Victor became increasingly strained during this period.
Waylon also includes a duet with Anita Carter on the Merle Haggard composition "All of Me Belongs to You." Jennings had covered two Haggard songs previously on his 1968 LP Jewels but, as he recounted in his autobiography years later, he became wary of the country star after a card game, recalling, "Merle Haggard and his manager, Fuzzy Owen, got me in a poker game and cleaned me out. I had four or five thousand dollars on me, and they won everything. I think Merle is a great singer and songwriter, and probably he was in as bad a shape as I was, but we've never been close since that night. I can still remember their faces. When I was broke, they said their goodbyes and left. I never forgot that."[2]
Critical reception
Waylon reached #14 on the Billboard country albums chart. AllMusic: "Waylon is an overlooked gem in the transition period of Jennings' career."
