Cantor Yossele Rosenblatt (1882-1933) was offered an opportunity that would make any performer swoon: a star role in the ground-breaking film The Jazz Singer (1927). Yet Rosenblatt refused this artistic opportunity of the lifetime. This paper contextualises Rosenblatt’s baffling decision, by exploring one possible relationship between art and law; in this case – the art of storytelling and the Jewish legal system. The study demonstrates where the two pursuits tread separate, unlinked paths to a common end. This vector is refracted through the lens of performance of prayers outside of the religious synagogue service; specifically the propriety of cantorial concerts that presented prayers from the High Holy Day liturgy. This issue appears in Jewish legal writing and in storytelling – each modality using its own tools to tackle the trend. It is noted that legal systems without effective enforcement mechanisms – such as Jewish law in the late modern period – could use arts as compensatory media for achieving societal order. More significantly, however, arts are not umbilically connected to law; each cultural creation independently strives to fashion society. The full article is available at http://ssrn.com/abstract=2612762.