In 1992, Chicago was experiencing a resurgence in their popularity, having successfully transitioned into the '80s with their more polished sound. The live recording of "Hard to Say I'm Sorry," performed on June 20, 1992, at Pine Knob in Detroit, was part of their concert video "And the Band Played On," which highlighted their greatest hits from previous decades. Prior to this concert, Chicago had released "Chicago 17" in 1984, which featured several chart-topping singles and solidified their place in pop rock. This period also marked the band's collaboration with producer David Foster, who significantly contributed to their sound. The performance of this particular song, co-written by Foster and former lead vocalist Peter Cetera, showcases the band's ability to blend pop and rock while capturing the emotional depth of their lyrics, reinforcing their status as a beloved American band.