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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 Records album commenced, she showed Prince the song. He decided to record it and reworked the lyrics, changing it to Pain. The song was registered twice at the Ascap : as Pain (Non-rap version), credited to Prince and D. Channsin Berry and as Pain (Rap version) credited to Prince, D. Channsin Berry and Monie Love (for unknown reason, the song was registered at the Library Of Congress in April 1993 as being written by Prince, Rosie Gaines and Monie Love).
Prince’s take on the track was recorded on 6 July 1990 at Metropolis Studios in London, England (on the same day as My Tender Heart and Streetwalker). Its copyright at ASCAP seems to suggest Monie Love recorded a rap on it, likely in 1991 or 1992, when she was contacted by Prince to work on Carmen Electra’s album. Even when it was potentially considered for Rosie Gaines, Prince recorded his own lead vocal on it as well.
Pain was included as the fifth track on the 16 September 1993 configuration of Rosie Gaines’ 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. Prince’s and Gaines’s versions both contain lyrics (on the break before the bridge) that were not kept for Chaka Khan’s version.
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. Khan’s 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, the day following Prince’s passing, his version was streamed on Rosie Gaines’s Facebook account. Rosie Gaines’ version was released a few weeks later as a stand-alone track through Amazon, iTunes and CD-Baby.
In 2023 Prince’s version was released in October 2023 as the third track of Vault Tracks part 1, one of the discs with previously unreleased tracks included with the Diamonds And Pearls Super Deluxe Edition.
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