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Former Reader staff writer John Conroy has a must-read article in Chicago magazine this month, about being the victim of an assault while biking down Lake Street on the west side, and what happened when he decided to confront his assailant. And since torture is regularly in the news right now, I'd suggest his 2000 book Unspeakable Acts, Ordinary People: The Dynamics of Torture. It's a remarkable work that deserves to be back in the discussion.
Related: I was fortunate enough to find a copy of Gary Rivlin's 1995 book Drive-By in the office library - it's not as well known as Fire On the Prairie, but deserves to be. It's the story of one drive-by shooting in Oakland, California - a short book, and a gripping read, but surprisingly information-dense; Rivlin tells the stories of the families involved, going back to the circumstances that led them to the neighborhoods the story revolves around.