Born Cheryl Bridget Riley in Brooklyn, Riley was the first of two children born to James Madison Riley and Lucia Viola Riley. Riley attended Clara Barton High School. After high school, Riley worked as a nurse for handicapped children before beginning her singing career. Riley began her music career as a lead singer in the band Stargaze, who released the single “You Can’t Have It” in 1982.

Riley married twice and has one child. In 1985, she married fellow Stargaze bandmate David Jones, but they divorced in 2000 after 15 years of marriage. In 2003, Riley married Chicago native Mike Grace, and together raised his son John Grace. In a recent interview with Lenny Green, Riley mentioned that she and Grace had divorced in 2011.

In November 1988, Riley topped the US R&B chart and hit the Top 40 on the pop chart at No. 32 with the ballad, “Thanks for My Child,” a song written by Full Force. The song peaked at No. 75 in the UK Singles Chart in January 1989. The genesis of “Thanks for My Child” began with Full Force member Bowlegged Lou’s experience with the complications of his wife’s first pregnancy. The title track single to her debut LP Me, Myself and I made it to number 18 on the R&B charts in early 1989. Another single, “Every Little Thing About You,” peaked at number 55 on the R&B charts later that year.

Following her appearance on a number of tracks on the Diary of a Mad Black Woman soundtrack in 2005, the following year Riley released Let Me Be Me, her first album in fourteen years. In 2015 she released a new solo album entitled Still Believe.