Your well-read uncle mentions he’s rereading Ulysses for the third time. Your literature professor aunt insists you simply must experience Gravity’s Rainbow. And you nod politely while thinking about the thriller on your nightstand.

These aren’t just any books—they’re the ones that separate casual readers from the truly devoted. What felt revelatory to educated boomers who had time to wrestle with dense prose now feels like homework to generations raised on tighter narratives. The books genuinely reward effort. But they also demand a reading style that’s increasingly foreign to how most people engage with fiction today.

1. Ulysses by James Joyce

Joyce’s 1922 masterpiece remains the Mount Everest of modernist literature. Every chapter uses a different style. The stream-of-consciousness sections require genuine stamina. One section arrives as a 60-page unpunctuated monologue that reads like someone’s unfiltered thoughts for an entire afternoon.

Well-read boomers speak reverently about Bloomsday celebrations and the novel’s revolutionary technique. They frame finishing it as an intellectual rite of passage. Younger readers typically abandon ship around chapter three, when Joyce pivots into pure interior monologue without warning.

The book rewards effort. It’s also exhausting in ways modern novels simply aren’t.

2. Moby-Dick by Herman Melville

Everyone knows the basic story—obsessed captain hunts white whale. What they don’t mention is that Moby Dick himself barely appears until the final chapters. The actual whale shows up for maybe thirty pages of a 600-page book.

Between the narrative, Melville inserts entire encyclopedic chapters about whale anatomy, the economics of whaling, and rope-making techniques. Chapter after chapter catalogs whale species or explores the philosophical implications of whiteness. It reads like three different books awkwardly bound together.

Boomers who love it frame these digressions as profound meditations. Everyone else wonders why nobody edited this down.

3. Gravity’s Rainbow by Thomas Pynchon

Pynchon’s 1973 novel about V-2 rockets in World War II holds a special place in literary history. It’s also aggressively difficult to follow.

The plot fragments into hundreds of characters. Scenes jump between reality and hallucination without signposting. Dense passages about physics appear alongside crude humor. One section features a sentient lightbulb. The whole thing refuses to resolve into conventional narrative structure.

Academics and devoted boomers praise its ambition and complexity. Most readers give up after 100 pages of trying to figure out what’s actually happening.

4. Infinite Jest by David Foster Wallace

At over 1,000 pages with 388 endnotes—some with their own footnotes—Wallace’s 1996 novel tests even devoted readers. The book jumps between storylines set at a tennis academy and addiction recovery center.

Wallace’s prose shifts from straightforward to deliberately labyrinthine. Entire passages demand multiple readings. The chronology scrambles on purpose. You need to physically flip between the main text and endnotes constantly, which disrupts any narrative flow you’ve managed to build.

Older literary readers call it a generational masterpiece that captures modern alienation. Younger readers mostly post photos of their bookmark stuck at page 200.

5. The Magic Mountain by Thomas Mann

Mann’s 1924 novel follows a young man visiting a tuberculosis sanatorium in the Swiss Alps. He plans to stay three weeks. The visit stretches to seven years, and so does the reading experience.

Philosophical discussions between characters span dozens of pages. Time dilates and contracts in ways that mirror the protagonist’s disconnection from normal life. Nothing much happens plot-wise for hundreds of pages. The pacing moves at glacial speed even by early 20th-century standards.

Educated boomers praise its intellectual depth. Modern readers accustomed to narrative momentum find it nearly impossible to push through.

6. The Sound and the Fury by William Faulkner

Faulkner’s 1929 novel tells one family’s story through four different perspectives. The first section arrives as stream-of-consciousness from a character with severe cognitive disabilities. Time jumps happen mid-sentence without warning.

The second section follows a character on the day he plans to die. The third adopts a more straightforward approach before the fourth switches to an outside narrator. You’re meant to piece together what actually happened across all versions. It’s a puzzle that demands effort most readers don’t want to give.

7. In Search of Lost Time by Marcel Proust

Proust’s seven-volume novel runs over 3,000 pages in most translations. One sentence famously continues for 958 words. The opening about eating a madeleine cookie spawns pages of memory and reflection.

The entire work operates as one extended act of remembrance. Plot arrives slowly if at all. Social gatherings receive exhaustive description. The narrator’s interior life matters more than external events.

Well-read boomers who’ve conquered all seven volumes speak of it with quiet pride. Most readers never make it past volume one.

Final thoughts

These books earned their reputations. Joyce revolutionized what novels could do. Melville’s ambition remains staggering. Faulkner’s techniques influenced generations of writers.

But defending them requires acknowledging what younger readers instinctively recognize—literary merit and readability exist on different axes. A book can be genuinely important while also being genuinely hard to finish. The cultural shifts that make these novels challenging don’t diminish their achievements.

The well-read boomers who treasure these books aren’t wrong about their value. Neither are younger readers who’d rather spend their time on books that don’t require a guidebook to decode.