The Playboy

As with every Chester Brown book, The Playboy—originally published in 1992—was ahead of its time, illustrating the fearlessness and prescience of the iconoclastic cartoonist. A memoir about Brown's adolescent sexuality and shame, The Playboy chronicles his teenage obsession with the magazine of the same name, but it's also a work that explores the physical form of comics to their fullest storytelling capacity. In it, a fifteen-year-old Chester is visited by a time-traveling adult Chester, and the latter narrates the former's compulsion to purchase each issue of Playboy as it appears on newsstands. Even more fascinating than his obsession with the magazine is his need to keep his habit secret and the resulting lengths to which he goes to avoid detection by his family and, later, his girlfriends.