Recovering from the Great Depression, America faced another battle-World War II. The Depression unknowingly prepared a generation to endure and to adapt to the kinds of hardships dealt to people during the war to end all wars. In Howling like Wolves from Longwood Drive, the author details the hardships endured by the youth of that era and the activities they were involved in-legal and illegal. Through a series of anecdotes, the book focuses on a group of teenagers from three communities on the far southwest side of Chicago from 1941 to 1945. This memoir describes how they entertained themselves, the risks they took, and how they solved problems. It tells of their hitchhiking escapades, the challenge of finding employment, the thrill of riding Chicago streetcars for free, and their brushes with the law.

In this memoir, Cunningham tells of how he and his friends learned vicariously of the horrors of World War II, in which most of his friends fought. Some of the friends returned home seriously injured. Some never returned. None were ever the same.