5 Great Books I Didn't Like the First Time

Added: 2026-06-04

[00:00:00]So, these are five books that I didn't like the first time I read them, but that now I've come to really enjoy and love.

[00:00:08]>> [music] [music] [music] >> Hey everybody, thank you so much for watching Leaf by Leaf. My name is Chris.

[00:00:24]I love that I can't stop reading books, and I love that I can't stop making book-related lists. So, finally in this five books series, I'm sharing some of my lists with you. I've noticed that there's a certain expectation that if a book is sort of heralded as great, there's an expectation that, well, our reading of it will be great. Or like that we'll recognize it right away.

[00:00:50]You'll read it, it'll land, everything makes sense, you fall in with all of those who agree, yes, this is a great book, or otherwise just respond to it immediately. But, of course, we all know that that isn't always the experience, at least not the first time. Some of the books that matter to me most are books that I didn't really care for the first time. Not because I misunderstood them exactly, but I think because I was reading them in a way that didn't allow them to work just yet. I was bringing undue, unreasonable pressure to them for the very first page. But over time, you know, something shifts. It might be that my expectations certainly have changed.

[00:01:29]I've become more patient, more forgiving. I've read certain things in between that unexpectedly prepared me more for the book. And just the simple fact that I've gotten more life experience. But when I returned to these books, something was just different. And again, of course, not because the book changed, but because I did. So, these are five books that I didn't like the first time I read them, but that now I've come to really enjoy and love. Number one is David Foster Wallace's Broom of the System, his debut novel. It's when people begin to fancy that they actually know something about literature that they cease to be literarily interesting.

[00:02:16]This was a strange experience the first time I read it because, unfortunately, I came to this after Infinite Jest. And in comparison, it sort of inevitably felt lightweight, loose, even a little juvenile. And yes, I know that it's unreasonable to use those to diminish the book when this is something that came out of his MFA. But the humor just felt more obvious, and the structure less ambitious, certainly. I read it in the shadow of the more mature work. But returning to it later, I started to see it anew. The play with language, the preoccupation at the Wittgensteinian level with language, that philosophical undercurrent, the way it's about meaning and reference. All of that, of course, was already there the first time I read it. So then, I was able to accept it not as the lesser novel, but as something just operating on a different scale and in a different mode. Once I adjusted for that, it became very clear how deliberate and precise this little banger is. Number two, Thomas Wolfe's Look Homeward, Angel, one of my favorite lines comes on the very first page. "O lost and by the wind grieved ghost, come back again." I've talked about this book and my experience with it several times on the channel. Basically, the first time I encountered it, I abandoned it about 75 pages in, tossed it aside, came back to it years later, couldn't put it down. The expansiveness of it and the density of it and the pace of its prose stopped feeling like excess and started feeling excess in a bad way, not in a good way. And it started feeling like a momentum of a different kind. The language accumulates. It doesn't just cleanly move forward. Once I began to read it that way, not expecting efficiency, but rather immersion, it became very difficult indeed to put down. It deserves its own video. Number three is probably the most shocking book on this list for people who know me and that is Moby Dick by Herman Melville.

[00:04:29]For whatever is truly wondrous and fearful in man never yet was put into words or books. And the drawing near of death, which alike levels all, alike impresses all with a last revelation, which only an author from the dead could adequately tell. At first this book seemed to me the loose bagging monster that Henry James talked about. It felt almost chaotic, unruly, uneven, like it wasn't certain of what it wanted to be.

[00:05:02]Narrative, essay, digression, and all of it just very loosely assembled. But over time and especially returning to bits of it like the much anthologized whiteness of the whale chapter, I began to realize that that instability I was sensing wasn't a flaw, but part of its deliberate design. The book keeps shifting just like Ahab going after the whale because it's trying to catch and hold something very large, too large for a single mode. And once you come to expect those shifts, they stop [snorts] feeling like interruptions and start to feel normal, honestly essential. Number four, La Peste by Albert Camus or The Plague by Albert Camus. A man can't cure and know at the same time. So, let's cure as quickly as we can. That's the more urgent job. My first reading experience with this was that it was just flat, almost overly spare, a little repetitive, even slow. It didn't deliver this emotional intensity that I expected when I came to it.

[00:06:16]that deliberate pacing is part of its point. Once we realize whose mind we're in, we realize how the character profile constrains the prose of the book. The tone is deliberately even because it's trying to represent a condition, something shared, collective, ongoing, but filtered through a single particular mind. And once you read it as less of a narrative of events and more of a sustained state of parallel meditation or background meditation, it opens up into something much larger than it at first presents, something profound and a true human dilemma. And finally, number five, The Great Gatsby by F. Scott Fitzgerald. I actually have a video on this one. The most limited of all specialists is the well-rounded man.

[00:07:12]This isn't just an epigram. Life is much more successfully looked at from a single window, after all. The first time I read this, it just felt slight, even quaint. I couldn't connect with any of the characters, and the scale of it just seemed so small-minded. But, when I returned to it later, what stood out wasn't really the plot, but the precision, the control of the sentences, the atmosphere, the way everything is shaped and placed. It's a book where really overall very little happens, yet every line carries so much weight. And once that becomes visible, it becomes very difficult to read this casually, such as I did the first time. What all of these books have in common is that they require a certain kind of orientation. And sometimes, as with my experience with these books, that orientation just isn't there the first time. But that's what makes part of returning and rereading so important.

[00:08:16]It's not just that you'll understand more later. It's that you are able to read differently. Sometimes failing the first time calibrates you in some way to be able to have a more successful second time, or third time, or fourth time. So, what are some books that you failed to connect with the first time that you now love?