In the live performance captured in the video "Chicago - If You Leave Me Now," the band was at a defining moment in their career. Released in 1976, "If You Leave Me Now" came from their album "Chicago X," which achieved significant commercial success, reaching number one on the Billboard 200 chart. This period marked a transition for Chicago, moving toward more ballad-oriented music that showcased their strong vocal harmonies and orchestral arrangements. Interestingly, this live recording reflects the peak of their popularity, as "If You Leave Me Now" became their first Grammy Award-winning song, earning the award for Best Pop Performance by a Duo or Group with Vocal. The live setting highlights not only the band's musicianship but also their connection with an audience that had come to appreciate their evolving sound.