Waylon Jennings – It’s Not Supposed to Be That Way

“It’s Not Supposed to Be That Way” is a song written by Willie Nelson and recorded by Waylon Jennings for his 1974 RCA album This Time. Jennings included the track among an album set that combined contemporary songwriter material with his own interpretive strengths; the recording reflects Jennings’s preference for plainspoken lyrics delivered with direct emotional honesty. The song’s authorship by Nelson places it within the community of Texan songwriters whose work Jennings often championed.

The recording sessions that produced the track emphasize a band-centered sound with minimal studio ornamentation. Jennings’s interpretation keeps the arrangement relatively spare—acoustic and electric guitars, steady rhythm and subtle harmonica or steel textures—so that the lyric and vocal phrasing remain central. This production approach matches Jennings’s stylistic move in the early 1970s toward more immediate, performance-forward tracks.

Lyrically, “It’s Not Supposed to Be That Way” frames a quietly fatalistic reflection on relationships and missed expectations. The narrator recognizes a mismatch between how things were hoped to turn out and the practical reality that has emerged; the song’s plainspoken wording and repetition of the central idea make the emotional weight feel inevitable rather than overwrought. That conversational, rueful tone suits both Nelson’s writing and Jennings’s interpretive voice.

Jennings’s vocal on the track is controlled and matter-of-fact, avoiding melodrama in favor of credibility. He delivers the lines with a steady phrasing that lets the listener hear the resignation in the words themselves; dynamic shifts are muted and the emphasis rests on storytelling clarity. The result is a performance that feels lived-in, which helped the song sit comfortably within Jennings’s catalog and within his live repertoire.

Though not issued as a major chart-topping single in Jennings’s catalogue, the song contributed to the artistic coherence of This Time and to Jennings’s reputation for choosing strong material from peers and contemporaries. The collaboration in choice of material—Jennings interpreting a Willie Nelson composition—also underscores the close creative exchange among several of country music’s leading figures in that era.

Today the recording appears on reissues and compilation collections that gather Jennings’s 1970s work and on streaming platforms where listeners can hear it alongside other Nelson-penned numbers Jennings recorded. The track is often noted by fans and historians as an example of Jennings’s interpretive judgement: selecting straightforward, emotionally precise songs and presenting them with a vocal approach that prioritized authenticity and narrative clarity.