Picture this: your well-read uncle swears that “Ulysses” changed his life, while your younger cousin abandoned it after page twelve, declaring it “literally unreadable.”
This divide between generations and their reading habits has been on my mind lately. After countless conversations with readers across different age groups, I’ve noticed a fascinating pattern. Books that boomers consider sacred texts often become the literary equivalent of kryptonite for younger generations.
Is it shortened attention spans? Different cultural contexts? Or maybe these books just haven’t aged as gracefully as we’d like to think?
Having grown up in a working-class household where books were treasured but scarce, I’ve always approached “classic” literature with both reverence and skepticism. Being the first in my family to go to university meant I encountered these supposed masterpieces later than most, giving me a unique perspective on their actual readability versus their reputation.
Let’s dive into eight books that perfectly capture this generational reading divide.
1. Ulysses by James Joyce
Every boomer intellectual I’ve met treats Joyce’s “Ulysses” like the holy grail of literature. They speak of it in hushed tones, describing how it revolutionized narrative structure and captured the entirety of human consciousness in a single Dublin day.
Meanwhile, most millennials and Gen Z readers I know have a dusty copy serving as an expensive bookend.
The stream-of-consciousness style that seemed groundbreaking in 1922 now feels like trying to read someone’s unedited Twitter feed after they’ve had too much coffee. When a friend recently asked me if they should tackle it, I suggested starting with something shorter first. Like “War and Peace.”
The truth is, “Ulysses” demands a level of commitment that modern life rarely allows. It requires not just time but sustained concentration in a world designed to fracture our attention every thirty seconds.
2. Atlas Shrugged by Ayn Rand
Few books divide generations quite like Rand’s thousand-page manifesto disguised as fiction. Boomers who came of age during the Cold War often cite it as a philosophical awakening, a celebration of individualism against collectivist threats.
But suggest it to anyone under forty, and watch their eyes glaze over faster than you can say “John Galt.”
The book’s length isn’t even the main issue. It’s the repetitive speeches that could make anyone question their will to live. That famous speech near the end? It runs for about sixty pages. In the age of TikTok, asking someone to read a sixty-page monologue about the virtue of selfishness is like asking them to watch paint dry in slow motion.
I’ve mentioned this before, but I have a weakness for political memoirs despite knowing they’re self-serving. Even I couldn’t finish this one.
3. Moby-Dick by Herman Melville
“Call me Ishmael” might be literature’s most famous opening line, but for many younger readers, it’s also where their relationship with Melville ends.
Boomers praise its allegorical depth and maritime authenticity. They see Captain Ahab’s obsession as a timeless meditation on human nature. Younger readers see endless chapters about whale anatomy and nineteenth-century sailing terminology that could cure insomnia.
A colleague once told me they tried reading it three times. Each attempt ended somewhere around the chapter literally titled “Cetology” – a scientific classification of whales that runs for pages. In an era where we can Google whale facts in seconds, dedicating chapters to whale taxonomy feels like punishment.
4. The Sound and the Fury by William Faulkner
Faulkner’s experimental masterpiece regularly appears on lists of the greatest American novels. Boomers admire its complex narrative structure and deep dive into Southern consciousness.
Try explaining to a Gen Z reader that the first section is narrated by a mentally disabled man with no concept of time, and that Faulkner deliberately made it confusing. Their response is usually: “So it’s supposed to be impossible to follow? And this is… good?”
The non-linear timeline that seemed innovative in 1929 now competes with content designed for maximum clarity and instant gratification. When you can stream a complex narrative that makes perfect sense, why struggle through deliberate obscurity?
5. Finnegans Wake by James Joyce
Yes, Joyce makes the list twice. If “Ulysses” is difficult, “Finnegans Wake” is practically written in another language. Which, technically, it often is – Joyce created multilingual puns and portmanteau words throughout.
Boomer Joyce enthusiasts treat it like a sacred puzzle, spending years unlocking its meanings. They join reading groups dedicated to single passages.
Show it to anyone under forty, and they’ll reasonably ask why they should decode a book when there are thousands of others written in actual English. It’s a fair question I still can’t answer.
6. Gravity’s Rainbow by Thomas Pynchon
Pynchon’s dense postmodern epic about paranoia and technology resonated with boomers living through the Cold War. They saw their anxieties reflected in its labyrinthine plot and system-level critiques.
Modern readers, already living in the surveillance state Pynchon imagined, find its 760 pages of paranoid complexity exhausting rather than revelatory. When reality feels like a conspiracy theory, reading hundreds of pages about conspiracy theories loses its appeal.
One friend described attempting it as “like being trapped in the mind of someone who’s consumed too much Wikipedia and acid.” Harsh, but not entirely unfair.
7. The Magic Mountain by Thomas Mann
Mann’s philosophical novel set in a tuberculosis sanatorium was considered essential reading for understanding European intellectual culture. Boomers praise its deep engagement with time, illness, and ideology.
Suggest it to younger readers, and they’ll wonder why anyone would voluntarily read 700 pages about people sitting around a hospital discussing philosophy. In our age of medical miracles and WebMD, the romanticism of tuberculosis and extended convalescence feels alien.
The glacial pace that allows for philosophical depth strikes modern readers as self-indulgent. Why spend years in a sanatorium with Hans Castorp when you could read three other novels in the same time?
8. Remembrance of Things Past by Marcel Proust
Proust’s seven-volume meditation on memory and time represents the ultimate generational reading divide. Boomers who’ve completed it wear it like a badge of honor, speaking reverently about involuntary memory and the nature of consciousness.
Younger readers see 4,000 pages about French aristocrats eating madeleines and attending parties as the definition of literary excess. The careful psychological excavation that enthralled previous generations now seems like the written equivalent of watching someone’s home movies in extreme slow-motion.
The bottom line
This isn’t really about intelligence or dedication. It’s about how dramatically our relationship with text has changed. These books emerged from a world with fewer competing media, longer attention spans, and different narrative expectations.
Reading before bed, I often choose something unrelated to current events – usually history or psychology. But I’d be lying if I said I regularly reach for these supposed masterpieces. There’s something liberating about acknowledging that just because a book is considered “important” doesn’t mean it’s essential for everyone.
Maybe the real question isn’t why younger generations can’t finish these books, but why we insist they should. Literature evolves with its readers. What spoke to one generation might simply have less to say to another.
The canon isn’t sacred. It’s a conversation, and conversations change with their participants.