The invention discloses a nested clingy flagpole painting device capable of adjusting climbing pressure. The structure of the nested clingy flagpole painting device comprises a paint spray, guiding pipes, a climbing device, a supporting base, and a clamping device, the guiding pipes are arranged on the two sides of the paint spray in a nested mode, and the lower end surface of the climbing devicefits the upper surface of the supporting base. The nested clingy flagpole painting device has the beneficial effects that under the function of a painting ring, once painting is only needed, the phenomenon of re-painting through multiple painting can be avoided; under the function of a stabilizer, drying can be conducted while painting is conducted, scratching is avoided; under the function of a height controlling gauge, the flagpole painting device is cooperated with the height, the painting force can be increased while the painting amount can be automatically reduced, and the stabilizer is attached to the outer surface of the upper end of a flagpole; and under the function of the clamping device, a torsion shrinkage device of the flagpole painting device can be tightly attached to the outer surface of the flagpole according to the diameter of the flagpole, the flagpole is prevented from shaking in the painting process under the influence of the wind, and the stability of the paintingis improved.