Gaines' first band was a family funk/soul group called Unity, with Gaines on organ, her brother Carl on bass guitar, her cousin Lacy on guitar, sister-in-law Dianne on background vocals and her sister Mal on drums. Gaines also played in a band called The Oasis and A Touch of Class before joining The Curtis Ohlson Band. Seacer called Gaines one day and asked her to come to Minneapolis, Minnesota to sing a demo of a song for The Pointer Sisters.
With Prince
While she was doing the demo, Prince came in the recording studio, was impressed by her abilities and asked her to join his band The New Power Generation. Gaines was introduced in 1990 as the new vocalist and keyboard player on Prince's Nude Tour. Her first appearance on a Prince album was on Graffiti Bridge, her vocals prominent on the second single, "New Power Generation". She was also a member of The NPG in the film Graffiti Bridge. She wrote and performed on the Diamonds and Pearls album, her lead and background vocals prominently featured on most of the album's tracks, including the hit singles "Gett Off", "Cream" and "Diamonds and Pearls". In 1992, after the Diamonds and Pearls tour concluded, Gaines returned to her solo career, although she continued to work with Prince from time to time. Prince produced the official remix to Gaines' 1995 solo single "I Want U", titled "I Want U ". She duetted with Prince on the live version of "Nothing Compares 2 U", which is available on his 1993 compilation album, The Hits/The B-Sides and also contributed vocals to the tracks "I Rock Therefore I Am", "Jam Of The Year" and a re-recorded version of "1999", which was released by Prince & The NPG in 1999. Gaines also appeared alongside Prince, Larry Graham, and members of The Family Stone in a special New Year concert in 1999, which was released on DVD under the title "Rave Un2 The Year 2000".
Solo career
Gaines recorded her first solo album, titled Caring, in 1985, followed by the 1987 album No Sweeter Love. Although neither album received much commercial interest at the time, both albums have subsequently been released in a digital format on iTunes. Following her 3-year tenure with Prince & The NPG, between 1990 and 1992, Gaines started recording her next solo album. Several albums worth of material were recorded, and an album was set for release on Paisley Park Records under the title Concrete Jungle. However it was not released because of a legal battle between Prince and Warner Bros. Records, and remained unreleased until 2010. Starting over, Gaines eventually released her third solo album on Motown Records in 1995. The album, titled Closer Than Close, spawned the singles "I Want U" and "Are You Ready?", and included the song "My Tender Heart", a song composed by Gaines and Prince and featuring background vocals by Prince and long-time NPG collaborators The Steeles, which Gaines had earlier performed on The Ryde Dyvine TV special in late 1992. In 1995 Gaines also collaborated with Tevin Campbell on the song "I2I", which was featured in the Disney movie A Goofy Movie. A club remix of Gaines' song "Closer Than Close" was released as a single two years later, in 1997. The "Closer Than Close" remix was commercially very successful in the United Kingdom, where it peaked at number four on the UK Singles Chart,. It also charted on the Australian club charts and has appeared on numerous club compilation albums. The track earned Gaines a MOBO Award for Best International Single at the ’97 Awards show, and inspired Gaines to record a follow-up club track, "I Surrender", which was released later that year. The remix of "Closer Than Close" is now considered a club classic, and has been re-remixed a number times since its initial release. With her own record label Dredlix Records, Gaines strove to bring her music directly via the Internet. In 1997, she released an Internet-only album, Arrival. Limited to 2,000 copies, it was available exclusively through her official website. In 2003, she released her album You Gave Me Freedom through Dome Records in the UK. In 2005, Gaines provided her vocals for the single "Dance With Me", which was recorded by K-Klass and released on SUSU Records. Gaines released her album Welcome to My World for SUSU Records in November 2006. She also self-released the albumSoul Survivor in 2013, which included 5 songs from You Gave Me Freedom alongside new and previously unreleased material. The compilation albums Essential Rosie, a 'hits' album of sorts, and Dance with Me, a club album that includes the singles "Dance with Me" and "Release the Pressure", were both released in 2015.