In August 2004, when Umphrey’s McGee performed at the Navy Pier Skyline Stage in Chicago, the band was in a dynamic phase of its career, having released their fourth studio album, "Anchor Drops," earlier that year in March. This album marked a significant evolution in their sound, integrating more progressive rock and experimental elements, reflecting their growth as musicians. The live recording from this concert showcases the band's tight musicianship and improvisational prowess, traits that have become hallmarks of their live performances. Additionally, the venue choice reflects their burgeoning popularity in the Chicago music scene, a crucial market for the band. Interestingly, “Anchor Drops” features various collaborative efforts and live staples that would set the stage for the band’s returning commitment to live improvisation and audience engagement, elements prominently displayed at this 2004 performance.