The concept of CCSA was developed in the early 1990s by a group of parents in Delaware interested in providing their children with an excellent academic education infused with the arts. They presented their idea to the Red Clay Consolidated School District and immediately gained support. The community embraced the endeavor and several local teachers, including former teachers Rich Hanel and Linda Emerick, took part in the creation of the school in 1992.

Soon after the school was founded, local arts and education activists were recruited to form the first Board of Directors. The school opened in September of 1992 as the Creative and Performing Arts Middle School. The following year it was renamed the Cab Calloway School of the Arts in recognition of Cab’s legacy as a performer and his ties to the local community. Cab’s daughter Cabella became involved with the school during her role as the Cab Calloway Fund’s Board President. In 1997 the high school program was established. CCSA celebrated its 25th anniversary in 2017 and continues to be an example of excellence of arts and academics.