A paintbrush-like image transformation is proposed in this paper. It is based on a random searching to insert brush-strokes into a generated image at decreasing scale of brush-sizes, without predefined models or interaction. One of the goals of the method is to transform the image into a representation that is very similar to the human sensation of artistic images. We introduce a sequential multiscale image decomposition method, based on simulated rectangular-shaped paintbrush strokes. The resulting images look like good-quality paintings with well-defined contours, at an acceptable distortion compared to the original image. The image can be described with the parameters of the consecutive paintbrush strokes, resulting in a parameter-series that can be used for compression. The painting process can be applied for scale-space image representation, segmentation and contour detection, and image representation for retrieval purposes.