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According to both experimental research and common sense, classical music is a better fit for figurative art than jazz. We hypothesize that similar fits may reflect underlying crossmodal structural similarities between music and painting genres. We present two preliminary studies aimed at addressing our hypothesis. Experiment 1 tested the goodness of the fit between two music genres (classical and jazz) and two painting genres (figurative and abstract). Participants were presented with twenty sets of six paintings (three figurative, three abstract) viewed in combination with three sound conditions: 1) silence, 2) classical music, or 3) jazz. While figurative paintings scored higher aesthetic appreciation than abstract ones, a gender effect was also found: the aesthetic appreciation of paintings in male participants was modulated by music genre, whilst music genre did not affect the aesthetic appreciation in female participants. Our results support only in part the notion that classical music enhances the aesthetic appreciation of figurative art. Experiment 2 aimed at testing whether the conceptual categories ‘figurative’ and ‘abstract’ can be extended also to music. In session 1, participants were first asked to classify 30 paintings (10 abstract, 10 figurative, 10 ambiguous that could fit either category) as abstract or figurative and then to rate them for pleasantness; in session 2 participants were asked to classify 40 excerpts of music (20 classical, 20 jazz) as abstract or figurative and to rate them for pleasantness. Paintings which were clearly abstract or figurative were all classified accordingly, while the majority of ambiguous paintings were classified as abstract. Results also show a gender effect for painting’s pleasantness: female participants rated higher ambiguous and abstract paintings. More interestingly, results show an effect of music genre on classification, showing that it is possible to classify music as figurative or abstract, thus supporting the hypothesis of cross-modal similarities between the two sensory-different artistic expressions.