Two books that really defined my views on cities:
The Geography of Nowhere
and
The Church and the Land

Essential reads for serious men in our times, in my opinion

The Geography of Nowhere by James Kunstler - Written in 1993, this book discusses the historical development of America's built environment in which we live, and the philosophical and moral ramifications of that environment. In this work, Kunstler argues that most of American architecture and cities, and indeed almost every acre of private and public land, has been shaped primarily by the automobile and simultaneous industrialization and free-market economics. The barrenness of our city-scapes, the ugliness of modern building, even the poor condition of the houses we live in, are all related to America being designed and built to serve the needs of machines rather than humans. The vast majority of this book dives into details of historical events, and Kunstler carefully traces the causal linkages between our built environment and technology. In the very last chapter, the author offers what he sees as the way ahead, out of the concrete morass we live in. His answer is to forcefully wean our society off of fossil fuels and reshape our cities to fit "greener", more human needs. This reviewer thinks his solution is idealistic and impracticable: our entire legal and material edifice is built on certain principles and inputs, and we have literally progressed too far to go back to a futuristic "noble savage" society. The advent of government incentives for electrified and smart everything in the name of "environmental responsibility" shows that our world would rather have automobiles than walkable cities.

The Church and the Land by Fr. Vincent McNabb (https://archive.org/details/churchland0000vinc) - The author of this collection of short essays was a Dominican priest about 100 years ago in London. The bulk of this book consists of strident criticism of what, at the time, was destroying the society of the West - namely the godless, heartless, anti-human system devoted to profit and progress. At Fr Vincent's time, governments and corporations were partnering to take advantage of new technologies which promised great things of the future for those willing to seize it: transportation, communication, efficient production, resource extraction methods. The only problem was that seizing the future meant discarding the past and trampling on human lives. Fr Vincent argues for a return to the land as the only hope for humans whose livelihoods, generational wealth, and even families were targeted and replaced by mass-production of low quality "luxuries", tenant slums with rampant disease and immorality, and ultimately an impoverished life disconnected from the land.

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I'm from the Midwest and Da Yoopers were family favorite road trip CDs