About the song
“This Time” is one of the most defining songs in the legendary catalog of Waylon Jennings, capturing both the emotional depth of his artistry and the creative independence that would soon reshape the entire landscape of country music. Released in 1974, the song not only became one of Jennings’ greatest commercial successes but also represented an important milestone in his transformation into a leading voice of the Outlaw Country movement. Written by Wayland Holyfield, “This Time” appeared as both the title track and one of the central emotional anchors of Jennings’ 1974 album This Time. It went on to reach No. 1 on the Billboard Hot Country Singles chart, marking Jennings’ first chart-topping hit—a key moment that propelled him firmly into country music stardom.
Musically, the track sits comfortably within the realm of Country, but with a stylistic edge that would later come to define Jennings’ signature sound. It blends traditional country instrumentation—warm acoustic guitar strums, emotive steel guitar phrases, and steady, grounded percussion—with Jennings’ deep baritone vocals, which carry equal parts grit, vulnerability, and conviction. The production, shaped during a period in which Jennings was gaining more creative control, is noticeably more relaxed and less polished than the “Nashville Sound” dominating country music at the time. Instead, it leans toward a more honest, raw, and intimate atmosphere, foreshadowing the freer, more rebellious sonic identity that would characterize his later collaborations with Willie Nelson, Jessi Colter, and other outlaw icons.
Lyrically, “This Time” is a heartfelt plea from a man desperate not to lose the love that he still deeply values. Instead of grand romantic declarations, the song takes the form of a personal confession, in which the narrator acknowledges the mistakes he has made and vows to change. The chorus, simple yet emotionally overwhelming, repeats the assurance that “this time” things will be different—this time he recognizes what he stands to lose, what he truly wants, and what he must do to keep it. Holyfield’s writing gives the emotional core of the song a frank and relatable tone, allowing listeners to see not just the pain of regret but also the vulnerability and hope that come with wishing for a second chance.
Waylon Jennings’ vocal interpretation gives the lyrics even greater emotional depth. His delivery is understated but powerful, a characteristic that would become one of his greatest strengths as a performer. Rather than leaning into melodrama, he conveys sincerity through a steady, introspective tone. There is a sense of maturity in the performance—an awareness of personal failure mixed with enduring affection—that resonates with anyone who has ever tried to repair a relationship that means more than pride or stubbornness.
At the time of its release, “This Time” marked a turning point not only for Jennings’ career but for country music as a whole. Jennings had been fighting for greater artistic freedom for several years, and his growing insistence on creative control—over song selection, production decisions, and musical direction—was a bold challenge to the industry norms of the early 1970s. The success of “This Time” validated that struggle. It proved that audiences connected more strongly with the honest, self-directed musical identity Jennings was carving out for himself than with the tightly controlled, producer-driven country sound that Nashville studios were accustomed to shaping.
The song’s popularity also helped pave the way for the Outlaw Country movement, encouraging record labels—reluctantly at first—to recognize the commercial potential of artists who wanted to break from convention and write, perform, and record music that reflected their own lived experiences rather than industry trends. In many ways, “This Time” provided the emotional authenticity and artistic confidence that would define Jennings’ greatest works in the decade that followed.
Even decades after its release, “This Time” remains a beloved part of Waylon Jennings’ musical legacy. Its themes of regret, redemption, and renewed commitment are timeless, and its blend of emotional storytelling with a raw, grounded musical style continues to resonate with country music fans across generations. The song stands as a testament not only to Jennings’ talent but to his ability to capture the complex and vulnerable sides of human relationships with unmatched honesty.