An excellent work of sociology that explores the roots and dynamics of poverty and housing segregation in American cities. This work is a bit old now, but even if you have read a lot on housing segregation, I'd still recommend this insightful book. The main argument is that housing segregation is the central cause of the "underclass," or the emergence of a persistently poor, crime-field, "pathological" set of AA neighborhoods in cities across the country. Massey explores the history of this segregation, including an outstanding chapter on the Fair Housing Act of 1968, in which he shows that the act only passed because it was gutted of enforcement provisions. The federal government then did very little to carry out the act (especially the Reagan admin, which was so hostile to fair housing and other civil rights provisions that it sparked the passage of a tougher fair housing act in 1988).
I thought what really made this book interesting was its explanation for how segregation causes and underclass and how this class' problems spread from one generation to another. The main point was that housing segregation concentrates poverty, which concentrates and normalizing the social/behavioral ills of poverty. Let me unpack this: If a segment of the population that is disproportionately poor is more evenly distributed throughout the population, it benefits from the variety of things that a slightly wealthier community usually provides: better schools, safer streets, more intact families, better relations with the police, inter-ethnic political alliances, etc. This is roughly what happened with many white and Hispanic groups, for whom housing segregation obstacles were far lower. If, however, a poorer group is concentrated together, and whenever the wealthier among that group tries to move the ghetto "follows" them as whites flee the area, social and behavioral problems become concentrated, intensified, and even normalized. The community, in a sense, becomes less than the some of its parts: people are moving around constantly (see the book Evicted for more on this), policing is more aggressive, norms about parenthood and upkeep of homes are reduced (in a population that already didn't have a lot of resources for these things anyway), and a kind of despair, anger, and short-term thinking can set in.
Massey only explores this dynamic for inner city black neighborhoods, where housing segregation, poverty, and crime are more intensely concentrated. However, I think it would be interesting to apply it to post-industrial white American towns and other contexts. I'd also say that this explanation of housing segregation's relationship to stubborn poverty could be accepted by both conservatives and liberals, although I think conservatives would have to go farther in setting aside the personal responsibility fixation.
This book also uses a handy measurement to show that African-Americans have been uniquely segregated in American history. It's an index of segregation that aggregates all the census tracts in a city and averages out the percentage of the average black person's neighbors that would also be black. SO if the segregation index is 90, that means that 90% of black people would have to move to other neighborhoods to achieve a perfectly integrated city. It means that 90% of the average black person's neighbors are also black. Chicago, for example, was hyper-segregated in the 70s and 80s, recording scores well over 90. I found this to be a really useful measurement for the level of segregation in a city. It also convincingly shows that old ethnic neighborhoods (Italians, Irish, etc), to the extent that we could measure, were never anywhere near as segregated as black neighborhoods, usually getting a score of around 30.
As you can probably tell, this is a heavily sociological work, but to me this is the best kind of social science work because it is a problem that screams out for good data. Massey is also a good historian, as he offers the reader a basic narrative of housing segregation and urban race relations in the 20th century. He also does a great job explaining how his argument challenges existing arguments (in the early 1990s) about inner city poverty and crime. I could see some people objecting to his argument as implicitly critical of majority African-American neighborhoods, saying that he's saying that it isn't good when a bunch of black people are congregated in the same places. That's not his argument though. His argument is that the unique exclusion of AA's from the mainstream of American life, including housing segregation and broader socio-economic mobility, has made the concentration of poverty in black neighborhoods a creator and sustainer of broader problems. It really has nothing to do with black culture inherently, contra many conservative rationalizations of black poverty. I think this is a really important contribution.