Emerging in 1990, “Wakin’ Up With You” by the legendary Waylon Jennings offered a softer side to the outlaw country pioneer. The song, featured on Jennings’ album “The Eagle”, marked a shift from his earlier rebellious anthems, showcasing a vulnerability and tenderness that resonated with longtime fans and newcomers alike.
While the exact songwriting credits remain debated, with some attributing it solely to Jennings and others suggesting co-writing contributions from Charlie Craig and Roger Murrah, “Wakin’ Up With You” undeniably bears Jennings’ signature stamp. The stripped-down production, overseen by producer Jimmy Bowen, emphasizes the song’s emotional core. Acoustic guitars and a gentle pedal steel provide the backdrop for Jennings’ weathered vocals, conveying a sense of weary hopefulness.
“Wakin’ Up With You” doesn’t shy away from acknowledging life’s struggles. The lyrics paint a picture of a man grappling with challenges and setbacks, feeling “a dollar short on a three dollar night.” However, the song ultimately celebrates the enduring power of love. The presence of a cherished partner becomes a source of unwavering support, a “dream to hold on to” that provides solace and strength.
Despite its introspective nature, “Wakin’ Up With You” doesn’t wallow in self-pity. The chorus explodes with a simple yet powerful declaration: “I know you’ll always be there right or wrong. Together we’ll keep on keepin’ on.” This sentiment resonates with anyone who has found solace and strength in a loving relationship, a testament to the song’s enduring appeal.
“Wakin’ Up With You” may not have been a chart-topping hit, but its impact lies in its ability to capture a universal truth. Love, even in the face of adversity, can offer a powerful anchor, a reason to keep moving forward. This simple ballad stands as a powerful testament to Waylon Jennings’ ability to connect with his audience on a deeply personal level, showcasing a tender vulnerability alongside his signature outlaw spirit.