The Homeless Heritage project (2009–2013) was a collaborative public archaeology project that sought to document contemporary homelessness from the perspective of homeless people in two British cities; Bristol and York. This paper will draw on case studies from the Homeless Heritage project and expand upon suggestions made in my recently completed doctoral thesis that participatory cultural heritage work can function as advocacy. Through close examination of the methodologies that were employed throughout the successful Homeless Heritage project, this paper will seek to highlight how relatively simple approaches may be useful in working with under-represented groups on heritage narratives. It will be shown how conversations and perspectives experienced as heritage can be redemptive for everyone involved, useful in promoting tolerance within diverse urban communities and ultimately help to enrich our wider understanding of our shared past and the complex ways in which our, sometimes conflicting, perspectives are woven together.