The group enjoyed its biggest success in the mid-2000s with their gold-selling albums Bluestars and Late Night Special, and the platinum singles "Grind With Me" and "On the Hotline".
[1] In 1997, while performing together in Miami, Pretty Ricky was signed to Bluestar Entertainment by CEO Joseph "Blue" Smith.
With the help from producer Jim Jonsin of the Unusual Suspects production team, Pretty Ricky began to gain desirable attention through their local performances.
However, it was not until 2002 that the group encountered their initial success as their song "Flossin'" became a huge hit on Miami radio station Power 96.
[7] The second single from the album, "Push It Baby", featured Sean Paul but failed to crack the Hot 100, reaching only #109.
This marked the return of Pleasure P.[16][17] In 2019, Pretty Ricky joined The Millennium Tour along with B2K, Mario, Chingy, Ying Yang Twins, Lloyd, and Bobby Valentino.
[18] On February 21, 2020, Pretty Ricky returned with a new single titled "Body", which is set to appear on the group's reunion album.