#277 | Arduous, Repetitive, Digressive, and Insanely Long—But Why Should You Read ‘Infinite Jest’ by David Foster Wallace?
Quick SUMMARY:
Douglas Vigliotti offers an in-depth review of David Foster Wallace’s novel "Infinite Jest,” discussing the book’s complex structure, disparate narratives, and major themes of addiction, isolation, entertainment, and societal critique. Vigliotti shares his personal experience tackling its challenging length, prose, and style, and highlights the novel’s enduring relevance for today, noting that perseverance in reading it might be central to its core message. He admits it was probably the most difficult book he’s ever read, but encourages men to give it a go if they feel compelled to do so.
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TOPICS COVERED IN the EPISODE:
Introduction to the Episode (00:09) - Douglas introduces the podcast, Infinite Jest, and promotes the companion newsletter.
About David Foster Wallace (01:19) - Brief background on the author, his influence, and previous podcast episode featuring him.
Plot Overview & Narrative Structure (02:18) - Summary of Infinite Jest’s three main narratives and how they interconnect.
Themes & Societal Critique (03:36) - Discussion of the book’s themes: addiction, entertainment, isolation, and societal commentary.
Genre & Authorial Intent (04:58) - Exploration of the book’s tone, genre, and Wallace’s unconventional approach to storytelling.
Challenges of Reading Infinite Jest (06:12 - Description of the book’s length, density, endnotes, and the difficulty of reading it.
Personal Reading Experience (07:26) - Douglas shares his struggle reading the book and why he persisted.
Style & Structure Reflection (08:50) - Analysis of how the book’s style mirrors the human mind and supports its themes.
Quotes & Final Thoughts (10:01) - Douglas shares key quotes from the book and reflects on their meaning.
Outro & Podcast/Book Promotion (11:06) - Closing remarks, ways to connect, and promotion of Douglas’s own book and the podcast newsletter.
READ THE TRANSCRIPT:
Welcome back to Books for Men, a podcast to inspire more men to read and bring together men who do so. I have a work of fiction to share with you today. It is titled “Infinite Jest” by David Foster Wallace. He is a repeat author on this podcast. This is a literary work of fiction. It is around 1100 pages or so. It came out in 1996, and I will get into all of that stuff. What I took away from it, how it almost broke me while I was reading it, and what you can take away from it, from reading it, or even just listening to this podcast, perhaps. But before I do that, I did want to just remind you of the companion newsletter that goes with this podcast, and that's just a once-a-month email that rounds up all of the episodes from that month, complete with full book and author information, all of my favorite quotes, episode summaries, and additional book recommendations. So if that sounds like something that you're interested in, or maybe you're already sold and you want to sign up, then all you have to do is head over to the website BooksforMen.org.
01:19 - All right. So let's turn back to the writer in the book, the reason why you are here. So, as always, I want to start with David Foster Wallace. I've already done an episode featuring him, as I already mentioned, which was actually a reprint of a speech that he gave titled “This Is Water,” and interestingly, it's probably his shortest printed work, whereas today, as I've already alluded to, is his longest. But since I've already introduced him in the other episode, which will be linked in the notes, I will be brief now and just say he was a very heralded and influential author of novels, essays, and short stories who, after a lifelong battle with depression, sadly took his own life at the very early age of 46. The book I am sharing with you today. Many consider it to be one of the great achievements in modern literature, and I can attest that it is also a feat for any reader. But before I get ahead of myself, I should just tell you what the story is about.
02:18 - I'm going to try to be brief, because the story is too convoluted to go into great detail, but in a basic sense, it involves three narratives: Story A, which is the primary one about how in cadenza and the trouble in cadenza. Family. They are the proprietors of Enfield Tennis Academy, where Hal also goes and competes as a nationally ranked amateur tennis player, and then Story B involves the cast of characters that you will meet at a Boston halfway house for addicts, and then Story C follows Canadian Radicals who are trying to free Quebec from an organization called the Organization of North American Nations. So you might have already gathered how disparate these narratives are, but I guess this is going to be sort of a spoiler. So just a heads up, they do come together through the final film of James and Cadenza, which is Hal's father, who actually committed suicide by sticking his head in a microwave oven. Fun little detail there. Of course, I'm being facetious, and the film is so compelling that people watch it incessantly until they die.
03:36 - So it's sort of like this metaphor for us as a society, and it is appropriately titled “Infinite Jest”, just like the book is titled, which is really a multi-layered satire about our need to pleasure ourselves at our own expense, trying to avoid the inevitable pain that's in our lives. So while it shows this through those different narratives tackling drugs and alcohol addiction more broadly, suicide, cheating, and entertainment in its various and endless forms. Hence, the title of the film and novel “Infinite Jest”. Filmography is a staple in this story, not just in the plot, but also as a form of escaping. And of course, there's like the multitude of stories you hear in the halfway house that are just wild and absurd, along with the entire story. See, really, somehow all of this juxtaposes off of each other to articulate the grand message, which again, or maybe this is a derivative of what I've already been saying. We're living in an overly commercialized society in which we cannot sit still, and our chosen consumption, or what we become addicted to, will eventually kill us.
04:58 - And I think where this book really continues to hit home, even to modern day, is that it's really about isolation and lack of connection, something that just feels so familiar and is such a pervasive problem. 30 years later, in 2025. So this book came out in 1996. I would call this book a tragicomedy, mostly because of its dark, comedic tone. But ultimately, the plot for me is a cautionary tale, teaching you a greater truth about life, which in my eyes makes it fall squarely into a tragic narrative. But ultimately, it's not easily categorized. And I think that that's by intention. David Foster Wallace doesn't really, I don't want to say care about the reader, but he does a lot of things that are counterintuitive with this book and that are very not reader-friendly, so to speak. It said that they cut 250 pages or so from the original manuscript of this, and it's still at 1100, so you can imagine how much was actually there. All right. So now there are probably so many reasons why you shouldn't read this book.
06:12 - It's long, it's arduous, it's repetitive. It's extremely dense. It's purposely digressive. There's almost no narrative thrust at all. I can honestly say it's the most challenging book that I've ever read. It took me close to four months, and I read it ten pages a day. I knew it was going to be challenging, and I just wanted to kind of get through it. And so I set a schedule for myself to be able to do so. You need two bookmarks to actually read it, because there are 300-plus endnotes. And even some of those endnotes have endnotes. So if you want to read the entire book, you have to constantly be flipping back and forth. And this is one of the things that makes it very challenging, but also because of the brilliant mind of the writer, quite often it's hard to follow what's going on, and you have to reread sometimes if you want to actually understand what is happening, you really have to work to piece things together. I would say it's just a very difficult read, and I can honestly say that after the first 150 to 200 pages or so, I don't know how any casual reader could actually enjoy reading it.
07:26 - It completely screwed up my reading schedule. And as I mentioned at the top of this episode, it almost broke me so many times. The topics are very heavy and combined with its style. I questioned whether I should finish it many, many times as I was reading it, but ultimately, I did. And so why would I read this? Especially when I have a rule of putting books down after a certain number of pages if I don't want to finish them. So I did it, to be quite honest with you, for the same reason why people climb Mount Everest. To say they did it, of course. Is it silly? Perhaps it is, but it's the reason why I did it nonetheless. And I will say that the meandering and the digression and the stream of consciousness style really does give you a feel of how the human brain works. And perhaps there is something baked into the style in which this book is told, and what the point of the actual work is. Can you sit still and read it, or do we have this endless need to find something that is more entertaining, more thrilling, even if it's at our own detriment, like drugs and alcohol and all the various things that can consume us and become medicinal in some ways?
08:50 - And so, yes, ultimately, I think the style and structure actually mirrors the human brain in a way, because of how quickly we shift and go on to tangents and whatnot, if we don't catch ourselves thinking about things. And so in a way, I think that that is additive to the theme and point of what Wallace is shooting for here. All right. So I will close this out with a quote or two. I didn't share many throughout this episode. Of course, there will be plenty in the newsletter, so if you're interested, go check that out. Sign up for it. But I will end how I started. I talked about how the previous episode that I shared was his shortest, “This Is Water”. Interestingly, the seed for that speech is baked into Infinite Jest on page 445. He writes: “This wise old whiskey fish swims up to three young fish and goes, ‘Morning, boys, how's the water?’ And swims away. The three young fish watch him swim away and look at each other and go, ‘What the fuck is water?’ And swim away.” So I won't go into great detail in explaining this quote.
10:01 - I did so in that previous episode, but obviously, the author feels strongly about it because not only is it in this book, but then again, he goes on to elaborate in a commencement speech. And I think that when you zoom out, it is a good lens on what David Foster Wallace is trying to articulate to all of us or show us in this story, perhaps. And then lastly, I want to share one quote that is a question he presents, and it's very short. And he says, “How is there freedom to choose if one does not learn how to choose?” I don't think that needs much explanation, so I won't give it one. I'll let you stew on it for a little bit. I want to thank you so much for listening and remind you that if you enjoyed this episode to please click subscribe on whatever podcast platform you're listening to this on, because it's the best way for new listeners to find the show and inspire more men to read. If you want to reach out to me, maybe tell me how I'm doing.
11:06 - You could do so in two ways: on Instagram @DouglasVigliotti. It's the only social media that I have, or via my website, DouglasVigliotti.com. I do have a new book out. It is titled “Aristotle for Novelists: 14 Timeless Principles on the Art of Story” and has just reached its one-year anniversary. And you could find out more information about it on the website AristotleforNovelists.com. Last but not least, if you want more information on this podcast specifically, which includes signing up for that newsletter I mentioned at the top of this episode, then all you have to do is head over to the website BooksforMen.org.
