“It’s So Hard to Say Goodbye to Yesterday” is a cover of G.C. Cameron’s 1975 hit, and the second released single from Boyz II Men’s first album, Cooleyhighharmony.

The song alludes to Cooley High, a 1975 film about two Black high school students in Chicago who are about to graduate from high school. There is a scene that plays the G.C. Cameron version of the song when Preach visits Cochise’s grave during the ceremony of his death. The movie is considered a classic in Black cinema, and it even inspired Boyz II Men to entitle their album Cooleyhighharmony.

FUN FACT: The vocal group sang this A Capella track during their days at Philadelphia High School for Creative and Performing Arts, which correlates well with the aforementioned references.

The song has a lot of historical context before the 90’s, but it was Boyz II Men who popularized it in mainstream media. It got a lot of radio airplay, peaking at #2 on Billboard’s Top 100 and becoming a #1 hit on the Hot R&B/Hip-Hop singles list. It also appeared in a few films, most notably in Lethal Weapon 3.