A painting system comprises a pressurized paint canister and a pressure fed paint brush or powered paint roller connectable to the pressurized paint canister. The canister includes a paint reservoir, a self-sealing gas pressure fitting in fluid communication with the paint reservoir and configured to be connected to a gas pressure source, a paint outlet in fluid communication with the paint reservoir, and a removable cap for filling the paint reservoir with paint. The brush assembly includes a main body having a handle and a brush stock and a bristle bundle secured in the brush stock. A plurality of fluid distribution members extend into the bristle assembly and are multidirectionally flexible such that the distribution members flex substantially freely with the flex of the bristles in any direction. The fluid distribution members prevent paint flow when in an unflexed state and allow flow onto the bristles only when flexed.