Jawaan Peacock, Benjamin Bush and Stephen Garrett met in the late 1980s and formed while the guys were still in high school. Smokey and Digital Black met through a mutual friend who thought the guys would sound good together, while Smokey and Static met in church while performing in a gospel group. Alongside other guys, the three men that would eventually form Playa created a group called A Touch of Class.
As A Touch of Class, the group met DeVante from Jodeci backstage at a concert. They began singing Boyz II Men songs when DeVante asked them if they knew any Jodeci songs. Essentially they impressed DeVante by performing a cappella versions of Jodeci songs backstage after a concert in 1991/1992. The guys were then signed onto DeVante's Swing Mob label with Elektra Records in 1993/94. Magazines such as Vibe and The Source attribute the signing to Static's close friendship with the boss and producers of the DeVante recording label. The group finally became known as Playa after DeVante heard the guys sing and called them "lil playas".
Other members of Swing Mob at the time were young hopefuls such as Missy Elliott, Timbaland & Magoo, Ginuwine, Tweet, and Renee Anderson. By 1996, most of the Swing Mob artists—Playa included—had left DeVante for better luck elsewhere. They participated in the production of Jodeci's The Show, The After Party, The Hotel album in 1995. During this time, the members of Playa learned production and built up a catalogue of material that would later be released as part of their Cheers 2 U album.
In 1998, Playa released their album, Cheers 2 U. The album featured production by Timbaland and Smokey and had two singles. The album's first single, "Don't Stop the Music" reached #26 on the R&B charts, while the second single, "Cheers 2 U" reached #10 and final single "All the Way" failed to reach to the charts (#98).
In 2002, Playa had plans to recorded their second album, Never Too Late, on Def Jam Recordings. They only spawned one single, "Never Too Late", which went no. 1 (only in Spain). But in the U.S., it went #59. The album shelved a few days after the single dropped.