Homelessness is an increasingly severe problem in many countries around the world. The homeless are often stigmatized by the rest of society. This essay explores how several contextual factors can moderate the expression of prejudice towards the homeless in two countries with different backgrounds, Hungary and the USA. Ambivalent opinions of the homeless exist in both societies, and prejudice is present to some extent in both, but especially in Hungary. Differences and similarities in public attitudes are related to specific challenges of a Western capitalist system, present in both countries, and of the legacy of Communism, unique to Hungary. Psychological mechanisms and cultural values also influence prejudice, such as the perception of threat towards the ingroup, a need for stability, individualism and belief in a just world. It is hoped that this essay can contribute to a complex and dynamic understanding of prejudice.