Kid 'n Play recorded three albums together between 1987 and 1993: 2 Hype  (1987), Kid 'n Play's Funhouse (1990), and Face the Nation (1991). Hurby "Luv Bug" Azor, the producer for Salt-n-Pepa who had been a member of the hip-hop group the Super-Lovers with Play, served as Kid 'n Play's manager and producer during the early portion of their career. All three albums focused upon positive lyrics backed by pop-friendly instrumental tracks. Among the group's most successful singles were 1989's "Rollin' with Kid 'n Play" (#11 on the Billboard R&B singles chart), 1990s "Funhouse" (#1 on the Billboard rap singles chart), and "Ain't Gonna Hurt Nobody" (another #1 rap hit). The group's stage show highlighted their teen-friendly personalities, and dances such as their trademark, the Kick Step.
Reid's visual trademark was his hi-top fade haircut, which stood six inches high at its peak. Martin regularly wore eight-ball jackets.

Kid 'n Play was also notable for their dance known as the Funky Charleston, or affectionately known as the Kid and Play, influenced by the 1920s-era dance move, first seen in their video "Gittin Funky". The Funky Charleston featured the New Jack Swing-aerobic dance moves typical of late 1980s urban street dancing (see also "Groove Me" by Guy). Unlike the original Charleston, The Funky Charleston/Kid and Play requires two participants instead of one. This dance also was made quite popular in the movie House Party, in which Kid and Play have an impromptu dance competition with Tisha Campbell and A.J. Johnson in one of the most memorable moments of that movie.