A handheld painting device is provided. In one example, the device includes an internal paint reservoir, an internally fed paint applicator configured to apply a liquid coating of paint to a surface, and a pump assembly configured to draw paint from the internal paint reservoir and pump the paint to the paint applicator. In one example, the device includes an internally fed paint applicator assembly configured to apply a liquid coating of paint to a surface, an elongate handle, and a paint pump assembly disposed between the paint applicator assembly and the handle, and configured to deliver paint to the paint applicator assembly.