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.

He sought a career drawing superhero comics, but was unsuccessful in finding work with Marvel or DC after graduating from high school.

After making a name for himself in alternative comics with the surreal serial Ed the Happy Clown, Brown turned to autobiography[4] 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.

[5] 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.

[9] 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.

[9] As an adult, he hunts down back issues and memorizes dates and names of Playmate models, and disposes of them over the guilt he feels or his fear of being found out by a girlfriend.

He began simplifying it after bringing Ed the Happy Clown to an end, as he had been reading work by cartoonists with simpler styles such as John Stanley and Brown's friend Seth.

[13] He made the drawings first and only afterwards laid down panel borders, which conform to the shapes of the pictures they enclose and are in a wobbly free-hand—much like those of the Hernandez brothers or Robert Crumb.

[16] He feels terrified of being caught masturbating and his regret afterwards drives him continually to rid himself of the magazines, such as by hiding them in the woods near his house, but always returns for them.

Comics critic Darcy Sullivan sees Brown in this scene having "shunted aside his painful feelings for her, and for other women, in favor of this tatty fetish".

[2] Some interpretations, such as those of Sullivan and Darrel Epp, see The Playboy demonstrating how the idealized images in pornography distort societal norms and expectations of beauty; one example cited is a scene in which Brown says he could only maintain an erection with one girlfriend if he fantasized about his favourite Playmates.

[17] Brown has objected to this interpretation—rather, he sees it as a flaw in the work, in that it does not provide enough context for what he intended to communicate: that he had gotten into a relationship with a woman whom he did not find sexually attractive, and that if Playboy did not exist he would have fantasized about other images of women.

[12] Brown stated that he intended a longer story encompassing what ended up in The Playboy and the following graphic novel, I Never Liked You (1994), but when planning it he found it was too complex.

[30] Critic Darcy Sullivan considered it required reading for those who are serious about comics[20] and a "landmark look at an artist's growth", referring to the pace with which Brown's work matured over the course of the three issues of its serialization.

[12] Hugh Hefner sent Brown a letter after The Playboy's publication, showing concern that someone who grew up during the sexual revolution could still suffer such confusion and anxiety.