There have, to date, been relatively few cases concerning homelessness and the Canadian Charter of Rights. Yet the rights set out in the Charter, such as the right to freedom of expression (s. 2(b), the right to life, liberty and the security of person (s. 7) and equality rights (s. 15) should all play an important role in protecting the position of a disadvantaged group such as the homeless. This article looks at some of the main cases concerning homelessness and the Charter (part I). It then goes on to look at the constitutional case law of the United States of America (Part II). The purpose is not to provide a comprehensive account of the status of US law nor to provide a comparative assessment of the extent to which the rights of homeless people are constitutionally protected in the respective legal systems. Rather the purpose is to identify the constitutional basis on which the rights of homeless people have been protected in US law. Part III then explores the implications of this in a Canadian context. The focus in this article is on laws adopt to ‘control’ homeless people such as anti-vagrancy, anti-begging or panhandling laws, and laws which restrict where (or how) people may, sit, lie or sleep.