All Of It with Alison Stewart

Episode: ‘Infinite Jest’ Turns 30

Original Air Date: February 10, 2026

Guest: Hermione Hoby (author, essayist, New Yorker contributor)

Episode Overview

This episode centers on the 30th anniversary of David Foster Wallace’s monumental novel Infinite Jest. Host Alison Stewart welcomes author and critic Hermione Hoby—whose recent New Yorker essay (“Infinite Jest Has Turned 30. Have We Forgotten How to Read It?”) reexamines the novel’s legacy. They discuss the novel’s reputation, structure, and cultural impact, as well as Wallace’s enduring themes: addiction, attention, loneliness, and the challenges of engaging deeply with challenging art.

Key Discussion Points and Insights

1. First Encounters & Personal Reflections on Infinite Jest

• Hermione Hoby’s Introduction to the Book
  • Hoby vividly recalls first reading Infinite Jest in her early 20s, after Wallace’s 2008 death.
  • She describes feeling both accompanied by the book’s immersive world and bereft upon finishing it.
  • Quote:
    • “I've read it twice...not ruling out a third, fourth, fifth time...When I finished I did feel a real grief, which no doubt was compounded by knowing that Wallace was gone.” (03:10)
• Wallace as Writer and Person
  • Hoby suggests Wallace would have been “horrified” by his literary sainthood, given his personal awareness of imperfection.
  • Quote:
    • “He was, you know, really allergic to the idea of, well, his own perfection…He was really aware of his shortcomings.” (05:36)

2. Plot and Structure: Ambition, Addiction, and Setting

• The Two Main Arenas
  • Enfield Tennis Academy: An elite, comic, and occasionally preposterous training ground for young tennis hopefuls—including Hal Incandenza.
  • Themes of Obsession: Characters are singularly focused on achievement, resulting in both farce and tragedy.
  • Quote:
    • “These very young kids become, you know, monomaniacal about getting better at tennis. They're always acutely conscious of their rankings within the school.” (07:33)
• Wallace’s Own Tennis Background
  • Wallace’s personal experiences as a ranked junior tennis player inform his depiction of the sport’s psychology. (08:58)

3. Character Analysis: The Semi-Autobiographical Hal

• Hal Incandenza as Wallace’s Stand-In
  • Hal, the brilliant and anxious young tennis player, mirrors aspects of Wallace himself.
  • His struggles and anxieties are reminiscent of the author’s life, but he isn’t the book’s ultimate hero.
  • Quote:
    • “Wallace…doesn't make him the main character…he was always trying to really heed and inhabit the reality and the humanity of other people, including people who weren't like him at all.” (09:32)

4. Addiction, Entertainment, and Prescience

• The “Fatal Movie” & Media Addiction
  • The book features a fictional film so addictive that viewers die from neglecting basic needs.
  • Hoby notes how Wallace presciently critiqued attention economy, foreshadowing our current screen addiction.
  • Quote:
    • “We have this…mass addiction to our smartphones, to doom scrolling...the corrective to that, to our shattered attention spans…is indeed to read a novel like Infinite Jest.” (11:54)
• Novel’s Length and Modern Attention Spans
  • The book’s 1,000+ pages make it increasingly challenging for contemporary readers conditioned by short-form media.
  • Hoby laments the shift toward “gamified” reading (counting books read over depth of engagement). (13:29, 13:52)

5. Reputation: Difficult, Pretentious, or Addictive?

• Challenging Yet Rewarding
  • Hoby pushes back against the stereotype of Infinite Jest as an unenjoyable, pretentious slog.
  • Quote:
    • “It's just a riot. It's just so fun and truly addictive, you know, and in this way enacts its own theme.” (14:02)
• Listener Perspectives
  • Listeners text in, describing the book as “unforgettable for its imagery, its humor, and its foretelling of our society today." (11:27, 15:02)

6. Language, Vocabulary, and Literary Style

• Wallace’s Word Choice
  • The novel’s advanced and sometimes obscure vocabulary is a frequent reader talking point.
  • Hoby recalls keeping a slip of paper for unfamiliar words such as “nacreous.”
  • Quote:
    • “To me, there is such brio and pleasure in these words. And…they are used incorrectly in a clever, funny way, which is when malapropisms are put in the mouth of one of the novel's least savory characters…” (16:51)

7. Female Characters and Gender Critiques

• Representation and Limitations
  • Main female characters Avril Incandenza (“the Moms”) and Joelle Van Dyne (“the Pea Goat”) are notably beautiful, which Hoby finds “dubious.”
  • While the book’s women are rich characters, Hoby notes that “the guys kind of get more...attention.” (17:57)

8. Wallace’s Personal Life and Legacy

• Allegations and Morality

  • Stewart raises Mary Karr’s allegations of abuse against Wallace.
  • Hoby differentiates between the ideals embodied in the fiction and Wallace’s real-life failings.
  • Quote:
    • “The moral force comes through the work, not through the life…that we can take the work on its own terms and try not to have the work too clouded by…abusive behavior that happened off the page.” (19:30)

• Addiction and Authenticity

  • Wallace’s own sobriety may have fueled the authenticity of Don Gately, a recovering addict central to the novel. (21:14)

9. Race and Representation

• Underdeveloped Portrayals
  • Wallace’s black characters are few and not well-developed, and Hoby finds this “awkward and painful to read now.”
  • She attributes it to the author “writing what he knew,” with tennis and addiction worlds largely depicted as white. (21:52)

10. Loneliness, Connection, and the Human Condition

• A Novel About Loneliness
  • Hoby emphasizes that every character is grappling with isolation—a theme that resonates throughout Wallace’s work and speeches (notably, “This Is Water”).
  • Quote:
    • “We really have this obligation to connect with each other, to be heeding the reality of other people…it's a book that makes you feel less lonely.” (25:48)

11. Advice for First-Time Readers

• Practical Tips and Encouragement
  • Hoby recommends turning off your phone to immerse yourself in the book's world.
  • She likens reading it to climbing a mountain: “Unlike real mountains, it gets easier and easier and more rewarding as you climb.”
  • Quote:
    • “I just hope a lot of people think of it not in a sort of eat your vegetables way, but just in a...life changing experience...” (24:46)

12. Cultural Legacy and 2026 Relevance

• Still Resonant—Perhaps More Than Ever
  • Despite (or because of) our more fragmented, lonely, and screen-addicted age, Infinite Jest’s themes are even more urgent.
  • Quote:
    • “It speaks more forcefully to 2026 than it even did to 1996…we need a book like this and its expansive humanity more than ever.” (27:39)

Notable Quotes + Timestamps

• On the book’s impact:
  “Truly, it was one of the great reading experiences of my life…when I finished I did feel a real grief.” — Hermione Hoby [03:10]

• On Wallace’s mythology:
  “He would just be really repulsed by the idea that he himself was the moral force rather than the work…” — Hermione Hoby [05:36]

• On Infinite Jest’s addictive quality:
  “It's just a riot. It's just so fun and truly addictive, you know, and in this way enacts its own theme.” — Hermione Hoby [14:02]

• On vocabulary and linguistic play:
  “There is such brio and pleasure in these words…language is sacred and wonderful and we need to honor it.” — Hermione Hoby [16:51]

• On reading advice:
  “Turn off your phone. Yeah, just turn off your phone and have a blast.” — Hermione Hoby [24:46]

• On loneliness and connection:
  “We really have this obligation to connect with each other, to be heeding the reality of other people… it's a book that makes you feel less lonely.” — Hermione Hoby [25:48]

• On the novel’s current-day relevance:
  “It speaks more forcefully to 2026 than it even did to 1996…we need a book like this and its expansive humanity more than ever.” — Hermione Hoby [27:39]

Listener Highlights & Memorable Moments

• Multiple listeners reached out (texts and calls), reinforcing the book’s profound impact and enduring mystery.
• David from Long Island City shared how the book was part of his recovery journey and how he left a copy in rehab, hoping to inspire others. [22:49]
• Another listener compared repeat readings of Infinite Jest to climbing a mountain—challenging, but more rewarding each time.

Conclusion

This episode offered a thoughtful, deeply engaged reflection on Infinite Jest at age 30, anchoring its continuing relevance in themes of addiction, attention, loneliness, and literary ambition. Hermione Hoby and Alison Stewart dismantled notions of the book as merely pretentious or prohibitive, recasting it instead as a vibrant, profoundly empathetic work—one that, in Hoby’s words, might be more necessary in 2026 than it was in 1996.

For any reader intrigued by Infinite Jest—or daunted by its reputation—this conversation offered both inspiration and practical encouragement: to engage deeply, to enjoy the ride, and to remember the shared human hunger for connection at the book’s core.