The article presents an empirical study of the depth of thinking - personal characteristics reflecting the process of understanding of the problem; object – the solution of problem situation with artistic content, actualizing productive thinking; goal – to identify the level of problem solving in correlation with its success. The theoretical basis – the ideas of Gestalt theory and the Matyushkin’s theory of problem situations about productive thinking and evaluation its success. The study shows that the depth of thinking reflects the levels of understanding of the sense of artistic works – from a misunderstanding to clear and explicit understanding of the sense of the work in accordance with the author’s intention. The levels are the basis for evaluating the success of problem solving. From the object of thinking the depth is determined by artistic genre: the greatest depth of thinking requires dramatic genre. There is the positive correlation of the success of the solutions for two types of problem situation with artistic content – understanding of the sense of the film and the story by fragments – with the dramatic and comedic content. There is negative correlation for the success of the solutions of problem situations of emotionally opposite genres – comic and dramatic – for two types of problem situations.