The Playboy is a graphic novel by the Canadian cartoonist Chester Brown, serialized in 1990 in Brown's comic book Yummy Fur and collected in different revised book editions in 1992 and 2013. It deals with Brown's guilt and anxiety over his obsessive masturbation to Playboy Playmate models.

The story begins with Brown's first purchase of an issue of Playboy as a teenager. His obsessive masturbation gives him great guilt and anxiety, and out of fear of being caught he repeatedly rids himself of copies of the magazine, only to retrieve them later. His conflicting emotions follow him into adulthood until he purges them by revealing himself through his comics. The free, organic arrangement of odd-shaped panels of simple, expressive artwork contrasts with Brown's more detailed grid-like pages in his 1980s work, such as Ed the Happy Clown.

The Playboy forms part of Brown's early-1990s autobiographical period, and was the first book-length work he planned as a complete story. Brown conceived it as a longer work with what became his next graphic novel, I Never Liked You (1994), but found the larger story too complex to handle at once. The story has attracted praise for its revealing honesty, and criticism from those who saw it as glorifying pornography. The Playboy publisher Hugh Hefner wrote to Brown to express concern over Brown's sexual anxieties in a post-sexual revolution world.

Chester Brown grew up in Châteauguay, a Montreal suburb with a large English-speaking minority; he does not speak French. He described himself as a "nerdy teenager" attracted to comic books from a young age. He sought a career drawing superhero comics, but was unsuccessful in finding work with Marvel or DC after graduating from high school. He moved to Toronto and discovered underground comix and the small-press community. He began to self-publish a minicomic in 1983 titled Yummy Fur.

Toronto-based Vortex Comics began publishing Yummy Fur in 1986. After making a name for himself in alternative comics with the surreal serial Ed the Happy Clown, Brown turned to autobiography after reading such work by Julie Doucet and Joe Matt. The work of his friend and fellow Toronto cartoonist Seth inspired Brown to pare down his drawing style during the early 1990s. He tentatively began his autobiographical period with a pair of short tales, and gradually became freer with his panel layouts and simpler in his artwork.

The autobiographical story takes place in Chester "Chet" Brown's hometown of Châteauguay in 1975, when Brown was 15. It details his obsession with the Playmates in Playboy magazine. Brown's character obsessively masturbates in secret, terrified of being found out, but unable to resist the urge. Afterwards he feels guilty and sometimes rids himself of the magazines, only to retrieve them. As an adult, he sometimes repurchases copies of issues he had discarded.

The story takes place primarily during Brown's adolescence and finishes at the time of the book's creation. Brown uses a bat-winged figure with his own face to narrate the story and goad Chet in a way similar to the trope of the angel and devil on the shoulders. Chet never acknowledges the narrator, who appears to be visible only to the reader. The narrator talks about Brown in the third person in the adolescent parts of the story, but in the first person in Brown's adult years.

The story opens in church, where the winged narrator cajoles the adolescent Chet to buy a Playboy magazine he had seen for sale. Chet works up the courage to buy it at a convenience store a considerable distance from his house, in the hope that no one will see him there.