A product of the Miami music scene, Pretty Ricky was originally a band of four brothers who went by musical pseudonyms: the rappers Slick 'Em, Baby Blue and Spectacular, and the crooner Pleasure P. The boys began performing together in 1997, with their father, Joe "Blue" Smith, taking the role of manager and taskmaster. (Smith is the father of all four, but only Spectacular and Baby Blue have the same mother. All were born between 1984 and 1986.)

In 2004 their single "Grind On Me" began to get heavy airplay on Miami radio, which lead to a deal with Atlantic Records and national exposure. The band specializes in synthesizer-heavy R&B that appeals to female listeners; "Grind With Me," a sanitized version of their hit single, powered their debut album Bluestars.

In 2005 the band toured with Omarion and other pop-friendly R&B acts in the Scream Tour IV concert series. Their second release, Late Night Special (2007), included the hit singles "On the Hotline" and "(I Wanna See You) Push It, Baby." Pleasure P left the band in 2007 and was replaced by vocalist 4Play in 2008. (Baby Blue began going by the name Diamond Blue the same year.)

Another singer, Lingerie, joined the band in 2009. Their later album include Eighties Babies (2008) and the extra-naughty Pretty Ricky (2009).

According to a 2005 story in The Miami Herald, the brothers "were originally called Pretty Rickie and the Maverix, until the country group the Mavericks objected, and the brothers decided 'y' endings are 'more masculine' than 'ie.'"