I think it also has to do with how influential an artist has been during and after his time i.e how much he or she contributes to the development of art history. Therefore it has less to do with how technically skilled or how soulful a work of art is, but how much it encompasses (and expresses for the masses) the zeitgeist that is on the brink of coming into existence - i.e. the feelings, morals, beliefs etc. that are still unconscious in the minds of most of the said artist's contemporary society. The surrealists (for example) were highly influential in the development of post-modernism, but quite a lot of them denied being technically accomplished (although one can argue that quite a lot of them were) or romantic or soulful in notion.
(Max Ernst's "Ein Kupferblech ..." below)
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