Set in Dublin at the Seabrook College for boys, Skippy Dies combines the visceral power of David Foster Wallace’s Infinite Jest with the raw anxieties of life in the 21st century. The result is a dazzling and uproarious novel in which nearly all the characters are at odds with one another (and with themselves) as they walk the line between fantasy and reality, spectacular deception and jaw-dropping revelation. While a ruthless Acting Principal (“the Automator”) tries to dissolve the school’s affiliation with the Holy Paraclete Fathers, faculty and students alike revel in unholy obsessions. For the teenage drug dealer Carl, it’s porn, laced with his borderline psychotic fantasies. For the pudgy young genius Ruprecht, it’s a quest to open a portal to a parallel universe. Unable to get his students to understand the magnitude of the Great War, the history teacher Howard Fallon spends equal time trying to get it on with his sexy colleague Aurelie. For Eoin “MC Sexecutioner” Flynn, life is an endless hip-hop soundtrack. As for Skippy, with a distracted father and a cancer-stricken mother, he simply dreams of a day when no one harasses him anymore. There’s not enough Ritalin in the world to bring normalcy to Seabrook, but then again, normalcy is all relative within those historic walls.

Hailed by The New Yorker as an author who “gets away with just about everything,” Paul Murray reinvents adolescence, adulthood, and storytelling itself in Skippy Dies. We hope the following questions will help your book club survive the exhilarating ride.

2. Why can’t Howard be happy with Halley? Is his obsession with Aurelie any different from Skippy’s obsession with Lori?

3. Who are the heroes and villains in this novel? Is the bad behavior due to bad parenting, high testosterone levels, materialism, lack of belief in a difficult God? Other factors?

4. How does Seabrook compare with your high school? Which characters most closely resemble you and your circle of friends?

5. What do the novel’s priests have to say about the nature of the suffering they see at Seabrook? Do they defy or fit the stereotype of prep-school priests?

6. When Carl’s parents fight loudly (David versus jealous mother Lucia), what do you think they’re teaching him about love? How do they manage to stay so clueless about their son?

7. With his emphasis on marketing, branding, and public relations, does the Automator (Greg Costigan) reflect a typical trend in education today?

8. Would the novel have been as interesting if it had been set at the all-girl’s school St. Brigid’s? Are teenage girls as destructive as teenage boys?

9. Howard tells the Automator that Skippy earned his nickname because he has buck teeth, which cause him to make a kangaroo-like noise when he speaks. What makes Skippy an easy target? Are those who pick on him (including Father Green, badgering Skippy about obscenity in front of the whole French class) sadistic?

10. Google “M-theory.” What do the articles seem to say about the search for order in the universe, even before the Big Bang? Why is it an ideal theory for Ruprecht’s obsession, and for this novel?

11. Part I closes with a blend of Professor Tamashi’s interview on the eleventh dimension and scenes from Skippy’s “seduction” by Lori. What does it take to give and get love in Skippy Dies? What do those scenes say about the reality that love creates? What does the novel say about the reality that drugs create?

12. Lori’s father, Gavin Wakeham, is an alumnus of Seabrook, and he is eager to share with Skippy his recollections of the faculty (which included a fondler, alumni who returned to their alma mater to teach when other opportunities didn’t work out, and the perennially socially conscious Father Green). What impressions did the school make on Mr. Wakeham? What impressions will it leave on Skippy’s class?

13. Discuss Ruprecht’s quartet and the musical performance he links to communicating with the dead. Is it a step forward or backward for him, mentally?

14. Which came first: Carl’s drug use or his obsession with power and violent sex? When he became haunted by Dead Boy, did you think he was seeing a hallucination or a ghost? Reread his explosive closing scene. Is he a Demon, or the victim of one?

15. After Skippy’s funeral, his father tells Howard that Skippy’s great-grandfather served in Gallipoli. Does Skippy’s generation lack valor?

16. Howard and Father Green are appalled to see the Automator defend Coach Roche. Is Tom worthy of defense?

17. Ultimately, who is to blame for Skippy’s death?

18. Discuss part IV, “Afterland.” Is Greg’s message a victory letter? Did he get everything he wanted?

Reading group guide written by Amy Clements / The Wordshop, Inc.