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This Article argues that a richer understanding of the nature of law is possible through comparative, analogical examination of legal work and the art of jazz improvisation. This exploration illuminates a middle ground between rule of law aspirations emphasizing stability and determinate meanings and contrasting claims that the untenable alternative is pervasive discretionary or politicized law. In both the law and jazz improvisation settings, the work involves constraining rules, others’ unpredictable actions, and strategic choosing with attention to where a collective creation is going. One expects change and creativity in improvisation, but the many analogous characteristics of law illuminate why change and choice are the norm in law too. Rarely is law just about ferreting out some isolated, clear, but abstruse legal command. In jazz and legal settings, relative assessments of strength are more commonly apt than are expectations of a single correct answer or simple binary right-versus-wrong determinations. There is a world of difference between claims that law simply provides determinate answers, versus claims that law constrains and guides what remain choices. Much as jazz improvisers must be highly sensitive to the surrounding constrained choices of others, legal analysis of context and consequences of legal choices, with substantial attention to others’ roles and competence, should always be part of legal actions. This different way of thinking about law’s nature helps illuminate and critique both major methodological legal divides, enduring jurisprudential debates, and several cutting-edge case studies. Those case studies include standing law’s transformation, including the 2021 TransUnion standing decision, ongoing battles over what waters are protected by the Clean Water Act, debates over textualist methodology’s claims of constraint, and increasing judicial reliance on the “major questions doctrine” with shifts away from the familiar deferential Chevron framework. Improvising musicians must ensure their choices musically fit with governing forms, practices, and others’ choices. Similarly, the Article closes by illuminating why, to further rule of law values and check power abuses, legal actors should always assess the consequential congruence of their tenable choices with surrounding law, giving substantial weight to statutory policies and linked effects analysis by agencies.

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2023 U. Ill. L. Rev. 151-224