Starting with a creative narrative inspired by the experiences of people who have spent time in prison, this chapter argues the need for a reality check. The truth is that repeated findings of poor physical and mental health in prisons have prompted calls for changes to policy and practice that are yet to deliver. It is likely that interventions will only be effective if they recognise the complexity of the relationship between health, crime and justice, and can respond to it. Evidence is presented to suggest that the arts may offer the imagination and reflectiveness needed to help shift the inertia, creating a more health-promoting rehabilitative culture. The arts peer into dark places and see the causes of crime and criminalisation. They have transforming effects on individuals and there is sufficient variability of impact to raise the potential for a humanities-based strategy for health improvement across the criminal justice system. The arts can't hold all the answers but may be where change begins.