With a career spanning more than four decades, Loudon Wainwright III has established himself as one of the most enduring singer-songwriters who emerged from the late sixties. Not only does he perform regularly across America and in Europe, but he is a sought after actor, having appeared in such movies as The 40-Year-Old Virgin, Knocked Up, and Sleepwalk with Me; and TV series ranging from M*A*S*H to Person of Interest to Parks and Recreation.

There is probably no singer-songwriter who has so blatantly inserted himself into his songs, about parents, grandparents, children, siblings, and wives. As he puts it in "So Many Songs": It's taken so long to finally see / My songs about you are all about me. The songs can be laugh-out-loud funny, but they also can cut to the bone. In his memoir, Wainwright continues to emphasize the personal: he details the family history his lyrics have referenced and the fractured relationships in the Wainwright family throughout generations: the alcoholism, the infidelities, the competitiveness—as well as the closeness, the successes, and the joy. Wainwright reflects on the experiences that have influenced his songwriting, including boarding school, the music business, swimming, macrobiotics, sex, incarceration, and something he calls Sir Walter Raleigh Syndrome.