Spanking Shakespeare, by Jake Wizner
Wizner, Jake (2007). Spanking Shakespeare. NY: Random House. 304 pages.
Shakespeare Shapiro is a victim of circumstance. First, his name: who other than crazy parents names their kid Shakespeare (and his brother Ghandi)? In spite of the fact that he is older (and wiser) than his brother, Shakespeare is in Ghandi's social shadow. At the beginning of his senior year, Shakespeare's desires seem almost attainable: he will win his school's memoir contest and finally find a girl willing to have sex with him.
Before you dismiss this book out of hand (as I almost did) for being just another one of those "school-assignment-turns-into-a-novel" books, give this one a try. Yes, it does include the main character's "writings" (in Courier font, no less) and, yes, these first-person writings supplement the already first-person framing narrative; however, somehow, the trope works in this book. Because Shakespeare's school assignment is to write his memoir, the alternative writings provide background and characterization, while the primary narrative details the protagonist's senior year.
By placing self-effacing and sometimes even disgusting comedy at the forefront of both plot and characterization, Spanking takes the school assignment trope a little farther than usual. Shakespeare's best friends--a mean girl who likes to get drunk and a loser-ish guy who loves to talk about his own poo--are "flawed" but hysterical counterparts whose presence almost mitigates the seventeen-year-old-virgin-looking-to-get-laid plotline. A smart and sarcastic narrative raises the literary bar from potential Last American Virgin and Little Darlin's territory to something more along the lines of C.D. Payne's Youth In Revolt.