The book chronicles the author's sixteen years of homelessness in New York City, aiming to humanize the city's unseen population. Cadillac Man, the author, details his descent into homelessness, the daily struggles, and unexpected moments of joy and bravery he experienced. The narrative is grounded in his personal recordings, written over years in notebooks, and includes the story of his relationship with a young runaway. His voice, described as gritty and poignant, aims to represent the broader homeless population while maintaining its unique perspective.

Dwight Garner of The New York Times described Cadillac Man's memoir as grueling yet not a grueling read, highlighting its ability to put human faces on the homeless population and noting moments of light, joy, bravery, and suspense. The book is recognized for its moving, funny, and unforgettable portrayal of homeless life in New York City. Cadillac Man's personal narrative, drawn from extensive personal writings, offers a gritty and poignant voice that speaks to the experiences of the nearly seven hundred thousand homeless individuals in the United States.