Pain by Chaka Khan is the fifth track on Living Single, the soundtrack album to the Fox TV series Living Single.
A preliminary version of the song titled Joy And Pain was written by D. Channsin Berry, for a future Rosie Gaines album. When Rosie Gaines joined Prince’s band and work on her Paisley Park album commenced, she showed Prince the song. He decided to record it and reworked the lyrics, changing it to Pain. While specific recording dates are not known, basic tracking took place in June 1990 in London, England (during the same set of sessions that produced Daddy Pop, Schoolyard and Walk Don’t Walk, but mostly focused on Rosie Gaines' first solo album, recording Hold Me, My Tender Heart, Streetwalker, In The Name Of Love and Turn Your Lights Down Low); Prince worked in three different London studios, Olympic Studios, Townhouse Studios and Metropolis Studios and it is not known which studio was used for this song. It was included as the fifth track on the 16 September 1993, configuration of Concrete Jungle, but was removed for later configurations. It was also included as the b-side on a planned single of My Tender Heart, where the writer’s credit was shared with Monie Love (it is not known if her contribution was removed from Chaka Khan’s version, or if her omission is an error). Specific recording dates for Chaka Khan’s version are not known, but the track, produced by David Gamson, was recorded between 1993 and 1995 at Ocean Way Recording, Hollywood, California, for inclusion on her planned tenth album Dare You To Love Me, which was postponed and finally canceled.
The released version of the track features Me'Shell Ndegéocello on bass guitar (who worked with on two instrumentals - one of which was later re-recorded as Emale), and renowned saxophonist Joshua Redman.
In 2016 Rosie Gaines released her version of the song through iTunes and CD-Baby