ABSTRACT Judicial legitimacy is an unexpectedly fragile convention in common law, frayed by the persistent tension between loyalty to precedent and sensitivity to the fluctuating socio-political values of the society. The nature of artistic legitimacy is intuitively more internal as raw imagination is channelled in order to create a purposeful work of art. Repetition, which can be an example of rebellious expansion in art, is found to contribute to continuity in a judicial setting. However, while artists can elect a repetitive practice, judges are necessarily confined to it. In both, the act of repetition gives emphasis to the slightest differences (after Deleuze) which become a focus of public scrutiny. This paper will identify continuity and expansion as two determinants of practice’s legitimacy. It will paint a picture of a judge and an artist who each build upon their own individual as well as collective legacy to legitimize the authority of their vocational action. It will draw parallels between the two practitioners in an effort to identify legitimacy as a driving force of professional practice, whether in law or art. Under such conditions, ‘practice’ will gain a new meaning: with every artwork, every judgment, an individual reinforces or fractures the legitimacy of their professional standing, depending on the extent and impact of the departure from the established (precedent) or acquired (artistic) path.