"It's So Hard to Say Goodbye to Yesterday" is an R&B song written by Motown husband-and-wife songwriting team Freddie Perren and Christine Yarian for the 1975 film Cooley High. In the film, the song is performed by Motown artist G.C. Cameron, whose rendition peaked at number 38 on the BillboardR&B singles chart that same year. Perren also composed the instrumental score for Cooley High, and the B-side to "It's So Hard to Say Goodbye to Yesterday" features two of his score compositions from the film.
The contemporary R&B Motown group Boyz II Men recorded the song in an a cappella rendition 16 years later. Released as a single, Boyz II Men's recording peaked at number two on the Billboard Hot 100 and reached number one on the Hot R&B Singles chart in December 1991. The track was included on Boyz II Men's first album, Cooleyhighharmony, its name a reference to the film from which the song originated.
A Cantonese version of "It's So Hard to Say Goodbye to Yesterday" was covered by Jacky Cheung. The song is titled "偷閒加油站" and it is featured on the 1992 album 真情流露.
In Lucifer series 5 episode 15, a version is sung by Ella Lopez (Aimee Garcia) and Lucifer Morningstar (Tom Ellis). It begins with Ella singing in Spanish before Lucifer joins in and they continue in English.
Latin pop group Barrio Boyzz performed the song acapella in Spanish at the Premio Lo Nuestro awards in May 1995 in honor of the late Tejano singer Selena, who was murdered two months prior.
The song was sung by Greg Miller of Kinda Funny fame, in the 2025 Tim Gettys Farewell Tour.
