Homelessness is a complex social issue affecting in excess of one billion people around the world. Despite varying definitions and cultural variations, key issues associated with homelessness appear to be similar across countries. Although New Zealand was once a country with high home ownership, recent governmental and welfare changes have contributed to a growing homeless population. Since contact between housed and homeless individuals is often limited, media coverage about the issue plays a vital role in the dissemination and distribution of information about homelessness and affected individuals. Although there are numerous studies analysing the portrayal of homeless individuals in overseas media, there is a distinct lack of comparable New Zealand based research. This study set out to investigate media representations and victim legitimacy of homeless individuals in the New Zealand news media, with a particular focus on how media representations and characterisations of homeless individuals may affect sympathy for them. This research encompasses both an overarching quantitative analysis of general reporting trends evident in the New Zealand news media (1995 - 2007), as well as an in-depth qualitative study of two particular case studies, namely media coverage following the murder of two homeless women, in order to further explore how sympathy can be supported or minimised, specifically during sad times. Findings from the content analysis reveal that homeless people are predominantly portrayed as negative stereotypes. Most were identified as rough sleepers, often depicted drinking in parks and socialising in public spaces. Homeless people rarely address audiences, as stories were mediated by professionals, journalists and service providers. Although there were aspects of the coverage that promoted a sympathetic understanding of the issue and affected individuals and moved beyond narrow characterisations and discussions of homelessness, the majority supported the typecasting of rough sleepers which resulted in a dichotomous, almost voyeuristic relationship between housed and homeless individuals. All in all, the New Zealand coverage appears unsympathetic as it typecasts individuals and perpetuates the 'othering' of homeless individuals The violent death of two homeless women was expected to yield very sympathetic coverage and tragic storylines. The first victim, Betty Marusich, was a 69-year old homeless widow whose decomposed body is found in the Auckland Domain. The second victim was Sheryl Brown, a 45-year old homeless mother of three. Despite initial assumptions, the analysis revealed little sympathy for either victim. Instead a negative reporting framework supported by typecast terminology, reporting techniques, derogatory characterisations and implied blameworthiness, challenged each woman's victim status. Ultimately, this chapter questions whether either woman was ever considered a true victim deserving of public sympathy at all. The study concludes with a discussion about the findings and how typecast representations, narrow characterisations, and marginal coverage can influence perception about the importance placed on, and extent of homelessness in New Zealand. Some suggestions for further research are discussed, as are recommendations to make media coverage more inclusive and less dichotomous in order to stress that homeless people are no different to housed individuals, but are merely individuals without suitable and affordable housing.