[2] Prior to entering politics, he worked for the National Office Furniture and the Protech EIS Corporation.

[2] He has also been a preacher, volunteer jail chaplain, music director, and piano player at Pleasant View Baptist Church.

[8] Although Republicans held a supermajority in both chambers of the Kentucky General Assembly, the party was split on the issue of gambling.

[8] In 2024, he criticized Governor Andy Beshear for issuing an executive order to ban conversion therapy for LGBT youth.

[9] In 2024, Calloway introduced legislation (House Bill 208) to propose an amendment to the Kentucky Constitution to allow public funds to be allocated to charter schools.