This paper examines two Tragically Hip songs, 38 Years Old and Wheat Kings, with a view to understanding how they can be interpreted as a call both to reform and resist criminal law. In a reformist spirit, 38 Years Old can be interpreted as an imaginary hypothetical that suggests that judges should be able to devise exemptions from all mandatory sentences, including life imprisonment for murder. The song can also be interpreted as a demonstration that imprisonment must be resisted and endured by offenders and their families because it will always be violent and destructive. Wheat Kings similarly can be interpreted as a call to reform remedies for the wrongly convicted and to make legal determinations of innocence. At the same time, Wheat Kings exonerated David Milgaard in 1992 long before the Canadian legal system did. In doing so, it illustrates how art, like media and science, can resist the coercive conclusions of the criminal law and can make normative conclusions that can be seen as a form of law.