This thesis presents a way of automatically generating a landscape painting in the artistic style of Bob Ross. First, a relatively simple, yet effective and versatile, painting model is presented. The brushes of the painting model can be used on their own for creative applications or as a lower layer to the software components responsible for automation. Next, the brush strokes and parameters used to automatically paint eight different landscape features, each with its own adjustable attributes and randomized forms, are described. Finally, the placement of all of the automated landscape features required to achieve the layout of one of Bob Ross's landscape paintings is shown.