Waylon Jennings delivers a quintessential outlaw country performance on 'It's Not Supposed to Be That Way,' a track that encapsulates the restless spirit of his career. Recorded for the 2010 compilation Double Play, the song reflects Jennings' signature blend of twang and vocal grit, characteristic of the genre that defined the 1970s. As a key figure in the outlaw movement, Jennings often explored themes of independence and the friction between personal desires and societal expectations. This recording stands alongside his extensive discography, including collaborations with Willie Nelson, showcasing his enduring ability to craft narratives of resilience and self-determination through his music.