"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 composition was recorded in an a cappella rendition by contemporary R&B Motown group Boyz II Men 16 years later. Released as a single, Boyz II Men's recording of "It's So Hard to Say Goodbye to Yesterday" peaked at number two on the BillboardHot 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. The music video for the song featured archive footage of Jim Henson, Sammy Davis Jr. and Gilda Radner, who'd all passed away one to two years before.
Singer Jacky Cheung recorded a Cantonese version of "It's So Hard to Say Goodbye to Yesterday" entitled "偷閒加油站" in 1993. The Notorious B.I.G. humorously refers to the song in the song "Gimme the Loot", from his 1994 album Ready to Die, indicating that if a potential robbery victim tried to resist his efforts, the victim's bereaved mother would be left singing "It's so haaaard." In 1995, Barrio Boyzz dedicated the song in Spanish to Selena after her death on March 31, 1995. In 1998, rapper Master P with Mo B. Dick, Silkk the Shocker, and R&B group Sons of Funk did a loose version of the song titled as "Goodbye to My Homies". In 2001, Usher sang the song a capella in memory of R&B singer and actress Aaliyah, who had been killed in a plane crash three days before. In 2002, Busch Stadium played the song while showing a memorial video of late pitcher Darryl Kile. In 2008, Jamelody included the song on his debut album, Be Prepared. In 2012, R. Kelly sang a portion of the song a capella in the ESPN 30 for 30 documentary Benji, which was a biography of Chicago HS basketball star Ben Wilson. Wilson was murdered in 1984 during an altercation with two teenagers at the age of 17 and Kelly was one of his AAU teammates. Kelly also sang the song as Wilson was being laid to rest the day of his funeral and recounted that for the film. In 2012, Angela Aki sang the song using both English and Japanese lyrics. In 2014, singer-songwriter Jason Mraz included the song on his fifth studio albumYes!, with rock-folk band Raining Jane providing back-up. Radio stations in the United States changing formats have on occasion used this song to sign off their old format prior to the debut of the new one, such as longtime urban station V103 in Baltimore in June 1997. On February 12, 2017, guitarist Josh Klinghoffer performed a short tease of the song during the Red Hot Chili Peppers show in Philadelphia
