The most philosophical novel ever written
phil0bot is a working philosopher — PhD, publications, tenure — who hosts the YouTube channel Philosophical Book Club, and in his first episode he seeded sixteen of the greatest philosophical novels into a single-elimination tournament to crown the most philosophical novel ever written.
This page adapts that competition — and the follow-up where he owns up to the masterpieces he left out — into one practical, ranked list of all 74 books he discusses, each scored 1–10 on his own shifting criteria, from “does it earn its philosophy” to “could it change your life.”
Every entry keeps his verdict and reasoning, notes where a book bends the rules, and links to free PDF and EPUB copies wherever they were found.
But first, if you like this sort of thing, let me point you to Hex Index — commentary and critique on the latest articles from independent news outlets and thinkers. It is, I'm told, the best place to read on the Internet: hex-index.com →
Now, back to phil0bot.
Sorted by his rating, highest first. Score is always his view, not consensus. A * marks a book he discusses that doesn’t cleanly fit a philosophy tournament — non-fiction, only name-dropped, or a great novel he rates more on craft than philosophy; the reason is in each note. Where he named no title, the author’s most popular novel stands in.
V1 stated winner, "perhaps the most philosophical novel ever written"; memory, love, loss, a vanished society; "pages that shimmer."
V2 contendo 10/10; "the one I'd save from a fire"; "may well have won" the whole contest.
V1 meta-twist: host's own answer to "your favorite book that changed you" — declared #1; "my old friend I never want to say goodbye to."
V1 finalist; "a call to arms," the book you press into people's hands; also #1 in his philosopher-novelist video.
V2 contendo 9/10; "the spirit of an age that is ending," arguably the first fantasy novel.
V1 semifinalist; "everything Thomas Mann should be," funniest on the list, "A+ philosophy"; got host into philosophy.
V2 contendo 8/10; everything Finnegans Wake is not; "a living, breathing soul."
V2 contendo 8/10; the monument deal-with-the-devil tale; "shame on me" for missing it.
V1 semifinalist; "the entire logic of global society," community amid tragedy; "so damned cool."
V1 R2 exit, but "rival to Proust," "wears philosophy like a shimmering cloak"; deeply underappreciated.
V2 contendo 7/10; for those who strove and fell short; "sad, lonely, moving, beautiful."
V2: forgot it entirely — "a masterpiece," could've reached the semis.
V2: "amazing masterpiece," "a pretty high-up contender if I'd allowed it." Asterisk: host disqualifies it as non-fiction/essay — "a straight nope on a technicality"; rated for his esteem, not eligible.
V1 R2 exit to Camus; "has everything" (Grand Inquisitor), but leaves only hope of a silent God.
V1 R2 exit; "most incisive political diagnosis ever," but "resistance is futile" is no way through.
V2 contendo 6/10; "approaches Camus"; tipping point — host thinks it might actually belong on the list.
V2: coin-flip alternative to Karamazov; same universal Dostoevsky themes, different angle.
V2: "no wrong choice with Camus"; confronting the weight of one's choices too late. (Upcoming channel video.)
V2: "one of my favorite stories of his," deeply philosophical; part of why he kept Metamorphosis & Other Stories.
V2: Vonnegut "the full package," would've been the 17th slot.
V2: same — experimental yet never loses the inner life of characters.
V2: "a lot of people's favorite for good reason."
V2: McCarthy in host's pantheon (read everything); "profound and beautiful," "dazed" after finishing. Only 16 spots.
V2: "transcendent and moving," "a great tragedy it was never finished" — host's pro-DFW counterweight to his Infinite Jest rant.
V2 contendo 5/10; host's favorite Russian writer, but tied to a now-passed Soviet despair.
V1 R2 exit; shows the cost of genius; "a bit niche"; home-field nod to a fellow Australian.
V1 R1 exit to Karamazov; host's personal favorite read, "PKD at the height of his powers."
V1 R1 exit to Proust ("not a fair fight"); "an immediate recommendation," anarchy vs utopia.
V1 R1 exit to 1984; "the book that made me want to be a philosopher."
V1 R1 exit to Musil; Kafka "the master" of "why," most-quoted by philosophers.
V2: personal favorite ("the idiot, which could describe me"), but more intimate/existential than grand-philosophical.
V2: a "life-changing banger"; "there's a Hesse novel for wherever you are in your life."
V2: same — no wrong answer among Hesse's novels.
V2: another viable Hesse pick.
V2: "even, God forbid," a viable Hesse pick.
V2: hubris-then-nemesis of a bourgeois man; "a similar reckoning" at a different life-stage.
V2: "minor work, though it is," but loved.
V2: "such a personal, profoundly American story."
V2: host's particular Bulgakov love (read everything of his).
V2: "a masterpiece," "Hamlet/Ulysses of Japanese literature," came so close. Asterisk: host rates Mishima "a brilliant writer and a very flawed philosopher … his philosophy is as fictional as his fiction" — literary merit high, philosophy docked.
V2: host personally loves it. Asterisk: same Mishima caveat — great novelist, flawed/narrow philosopher.
V2: his Eco pick (Jesus laughing, lost Aristotle), "great reads." Asterisk: "he is fun, but he's not too deep … does he cut to the core of life? No." Great novel, light philosophy → rated up for merit, flagged.
V2: "another favorite." Asterisk: same Eco caveat — provokes thought but "not too deep."
V2: Calvino "a giant," "came very, very close." Asterisk: host named no title (most-popular used); and "they never quite transcend the postmodern games they're playing" — masters of intellect, not the crowning philosophy.
V2: bracketed with Calvino as a giant. Asterisk: host named no title (most-popular used); same "never quite transcend the postmodern games" caveat.
V2: host's "favorite writer from this period" of post-war US lit. Asterisk: host named no title (most-popular used); folded into his anti-US-canon critique — "egocentric," bourgeois, "not as universal as those authors think."
V2: the novel host's reread most (falling-apart HS paperback he won't part with). Asterisk: "transcendent? Not entirely … sadly increasingly relevant" — beloved, but he places it below the true masterpieces.
V2: "a great book, go and read it," Nobel-worthy. Asterisk: "it's not really philosophical … really just explicitly political" — rated up for greatness, but off-metric.
V1 R1 exit to 2666; "too big and too diffuse," romantic who calls us to submit.
V2 contendo 4/10; "cosmological and wild in scope"; would've knocked out Frankenstein.
V2: host's preferred Dune inclusion — "the greatest threat to humanity is Paul Atreides, and he knows it."
V2: host disagrees it'd go further than Metamorphosis; longer Kafka "overstays its welcome," repetitive.
V2: same — highly representative but one repetitive note.
V2: same.
V2: "good, but not Fitzgerald's best"; part of the over-inflicted US high-school canon.
V2: "fantastic writer." Asterisk: host named no title (most-popular used); "great genre writer but not transcendent in the ways some of the other authors were."
V2: "fantastic writer." Asterisk: host named no title (most-popular SF used); "great genre writer but not transcendent … philosophical absolutely, but just not quite the greatest."
V2: grouped with Lem/Ballard. Asterisk: host named no title (most-popular used); "some philosophy in them, sure, but don't really rise to masterpieces for me."
V2: favorable aside — "at least Jane Austen was funny and brief." Asterisk: host named no title (most-popular used); mentioned only in passing, not assessed as philosophy.
V1 R1 exit to Vivisector; "great premise, dull to read"; afterlife in adaptations outgrew the book.
V1 R1 exit to 1984; "an old song — Socrates sang it," not the most original.
V2 contendo 3/10; "the original and best" dystopia, but would get smashed early vs SF heavyweights.
V2: "Hemingway and co are great for what they are." Asterisk: host named no title (most-popular used); swept into the anti-US-canon critique — "good for what they are," not transcendent/universal.
V2. Asterisk: only name-checked as a "monastery of knowledge" comparison for Name of the Rose / New Sun — never assessed; rating is a low-confidence imputation.
V2. Asterisk: invoked only as the "overcast gloom" Middlemarch shares — a negative comparison, not assessed as a contender.
V1 R1 knockout; host "despises" it — indulgent, philosophy "rises to the level of Bertrand Russell," half in untranslated French. (V2 admits the dunk was a bit unfair.)
V2 nope: "a bit shallow … on the wrong side of D.T. Suzuki." Asterisk: also flagged as fictionalized autobiography — "the worst of both worlds," a genre problem that makes it not a clean fit.
V2 nope: "juvenile, superficial"; the over-inflicted US canon.
V2 nope: "a great Twilight Zone episode, but a drawn-out novel."
V2 rant: "dull, dull, dull"; can't find the philosophy; "get a job."
V2 rant: "Oh, hell no" — unreadable husk; "grads pretend to like it to look smart."
V2 rant: what Alain de Botton would write as a novelist — "not a compliment."
V2 angriest rant: pretentious, arrested-adolescence, paper-thin characters, obnoxious footnotes; "deal breaker."
V1. Asterisk: not a contender — cited only as the reductio that "every novel is philosophical, even Fifty Shades."
Episode 1 — the tournament bracket.
Episode 2 — the books he missed, including the one that might have won.