As most soul fans first heard it when it was released in 1975, "It's So Hard to Say Goodbye to Yesterday" was a bittersweet song about moving to a new chapter in life. Freddie Perren - a member of the production collective known as "The Corporation" at Motown - penned the tune with his wife Christine Yarian for one of the label's utility players to sing: G.C. Cameron, formerly of the soul group The Spinners. His version, heard in the soundtrack for the 1975 high school film Cooley High, was a minor Top 40 hit on the soul charts.
It took an unspeakable tragedy that befell another Motown act just over 15 years later to turn the track into a touchstone for another generation. In 1991, Boyz II Men were one of the label's most exciting acts; the Philly quartet combined the sweet harmonies of forebears like The Temptations and the Four Tops with head-snapping New Jack swing beats courtesy of producer Dallas Austin. Their debut album, Cooleyhighharmony, took its name from that film they enjoyed so much, and "It's So Hard" began a slow climb toward the top of the pop charts, reaching No. 2 on the Billboard Hot 100 by Christmas 1991.
But the song took on new significance on May 25, 1992, while the group were touring alongside rapper MC Hammer. The group's tour manager, Khalil Rountree, was shot and killed during a stop in Chicago. From that point forward, the song was dedicated to his memory in concert. Perhaps it was his memory - to be the group's sunshine after the rain - that helped them achieve even greater success throughout the rest of the '90s.