DeVaughn took up a job at Tower Records, where while putting price tags on CDs, he began working the D.C. music circuit--performing with various groups and at venues such as the State of the Union and Bar Nun on U Street NW, all while having CDs of his songs ready at hand. Locally in the DC Metro area he attained relatively quick success, winning local awards and successfully releasing some independent work over the next few years. He won $2,000 from the Washington DC nightclub Bar Nun talent show. Jerry Vines, now the singer's longtime manager, met DeVaughn while managing the Baltimore-based quartet Dru Hill and asked him to write a song for the group. DeVaughn ultimately gained the attention of veteran producers DJ Jazzy Jeff (as Rahiem) and Kenny Burns (known as former A&R for Roc-A-Fella Records) and with the help of Vines signed a recording contract with Jive Records in 2002.

DeVaughn's first solo single released on a major label was the song entitled "Guess Who Loves