At the time of the live recording of "Stay Positive" at the Pitchfork Music Festival in July 2008, The Hold Steady had just released their fifth studio album, also titled *Stay Positive*, earlier that same month. This album marked a pivotal moment in their career, showcasing a blend of their signature storytelling and anthemic rock sound. The release proved to be well-received, debuting at number 30 on the Billboard 200 chart, highlighting their growing popularity. Notably, the album features themes of resilience and hope, reflecting the band's experiences and perspectives. The live performance at Pitchfork, a key indie music festival, illustrated their ability to captivate an audience, solidifying their status in the indie rock scene. Having previously been celebrated for energetic live shows, this performance further established The Hold Steady's reputation as dynamic performers, combining engaging lyrics with a robust stage presence.