Bryson Bernard first began to sing in his church's choir, encouraged by his pastor father. Despite his enrolling at The University of Louisiana at Lafayette with a full athletic scholarship in track and field, his real passion was still music. He left the track team to form a singing group and eventually dropped out of college. The dissolution of the group didn't sway Bernard's pursuit for a singing career as he went solo immediately after. He sang at every type of venue he could, including at talent shows, weddings, and funerals. With his five-octave vocal range, Bernard earned the name Cupid during this process for his impressive performance of the late-'90s 112 hit single "Cupid."

The singer first enjoyed radio airplay in 2001 with his single "Do Ya Thing," which appeared on his self-pressed, eponymous debut the following year. His gospel-tinged vocals began to attract local promoters and rappers alike as Cupid was tapped to open for blues concerts as well as to record background vocals for various rap albums. Both experiences informed his second independently released album, The King of Down South R&B (2005), which contained elements of country, blues, and New Orleans bounce music.

In late 2006, Cupid was finally discovered by Atlantic because of the enormous buzz surrounding his latest local single at the time, "Cupid Shuffle". He signed with the label that following January, and soon his dance record was standing its ground in the Top 30 of the R&B charts for several weeks. His major-label debut, Time For A Change, arrived later in the year.