After a long string of new (to me) books, I recently decided to pick up one that I have read before: Lord of the Rings, The Fellowship of the Ring. Rereading books was something that I did often as a teenager and young adult because I really enjoyed living in worlds where I knew I would be comfortable and in which I could dig deeper into familiar ground. I was wary of revisiting Tolkien because I didn’t want to ruin it. One always risks the destruction of good memories when the past returns. But the imprint of the movie versions was on my mind, and I could hardly remember the intricacies of the actual story that I had loved reading in early high school. Now, midway through The Two Towers, I have found the story deeper, better-written, and more rewarding than I remember, perhaps because the first time through I was too young to see beyond the surface of much in the world.
In light of my recent success in opening an old favorite and finding enjoyment in it again, here is a list of books that I have read at least twice, and whether they held up upon a second look later in life.
This Side of Paradise, By F. Scott Fitzgerald ❌
This was one of two books that I distinctly remember igniting my interest in literature. (The other was a play, The Importance of Being Earnest by Oscar Wilde.) I became enamored with the way the young Amory Blaine, a not-at-all-disguised fictionalization of Fitzgerald himself, was able to translate his feelings as he came of age, dealing with the same internal and external conflicts that I had as a boy. This is brilliant, I had thought. This is so relatable and deep, I had thought. The “romantic egoist” in me had been unleashed. I quickly bought Fitzgerald’s other novels and short stories, finding the same enthrallment in The Beautiful and Damned, The Great Gatsby, and Tender is the Night. I fashioned myself a clever social philosopher of the middle-class- and white-male-dominated Midwest, bringing culture and lofty opinions to my crude peers, or at least trying to…until I realized no one was interested in the ramblings of a precocious suburban literary fanboy who didn’t know much of anything about life beyond his dirt-road home.
In college, I opened Paradise again, hoping to revisit my literary awakening. By the time Amory, recently dropped out of college, flung his arms up at the “crystalline, radiant sky” and shouted “I know myself…but that is all,” I felt embarrassed, for me and for the young Fitzgerald. No wonder he had had such a difficult time getting the thing published. What had I seen in it before? What had even connected with me? All I can think is that I was so enamored by the brilliant syllable-by-syllable flow of Fitzgerald’s prose—like a gently sloping meadow full of purple wildflowers inviting you to play in it—that I didn’t bother to notice the thorny vanity beneath it, the banal ambitions of an upper-middle-class social climber, or the complete lack of an interesting plot.
The Great Gatsby, By F. Scott Fitzgerald ✅
This book shows that even if you suck at something, you can hit gold if you keep trying. All the elements that I found narcissistic and superficial about This Side of Paradise the second time around did not appear, even slightly, in Fitzgerald’s most famous work. Using the same themes and topics that appear in almost all of his stories—the social ambitions of the American middle class, disillusionment with the American dream, the aimlessness of chasing wealth, and uncomfortable encounters with romance—he finally stepped out of his own way and spoke exclusively through his characters and their story. The result is a tight, beautifully flowing masterpiece of a novel that deserves its place in the bookbags of high school freshmen across the United States.
The Harry Potter series, By J.K. Rowling 🧙🏼♀️🤔
I’ve reread Harry Potter books more than any others combined, and on my latest attempt I encountered a sort of fatigue, especially in the early titles. The first two, though necessary to set up the story that follows, definitely play to their younger target audience. And the final one, Deathly Hallows, although it has some of Rowling’s best epic writing, relies too heavily on her favorite theme: love conquers everything. Getting to the end of that book was thrilling, the first, second, and third times through, but the ending is a bit too saccharine for the evil-world story that is being wrapped up. There are some hard-hitting deaths, but the look into the future that caps it all is overly rosy and sentimental. She might as well have just dashed off, “And they all lived happily ever after.”
Overall, I’ve found that the intended audience of the books tracks the age of the main trio—Harry, Ron, and Hermione—rather well. So someone who begins reading them at, say, age 11 will probably get the most out of them, but children of all ages after that point will find something that speaks to their development and interests eventually in the series. Not a bad tactic for appealing to a large base of preteens and teens who will loyally follow the series through to completion as they grow up with the characters. I was 10 years old when I started reading them, and the final installment was published when I was 17, so I was just about as primed as could be to become an HP nerd. Now, although I’ll probably read all the books again at least one more time, I don’t feel the need to constantly escape my muggle world and enter Rowling’s mythology.
Hamlet, By William Shakespeare ✅
I’ve read Hamlet about five times completely now, but I plan to read it at least twenty more times as long as I reach the average life expectancy for someone of my demographic. I don’t need to praise or justify putting on my list the undisputed heavyweight GREATEST PIECE OF LITERATURE OF ALL TIME, but I will say that it possesses enough ambiguity and dark corners to keep literary enthusiasts thinking and commenting for as long as it is translated into whatever future languages will be used in this world.
Twelfth Night, By William Shakespeare ❌
This was one of my favorite Shakespeare plays the first time I read it. The second time, I wish I had just reread Hamlet. The story is fun and the language is interesting, but in the depth with which Shakespeare usually writes, I found it lacking. The important parts of the story are in plain sight. A few of the secondary characters have some lines that make me stop in admiration (although they don’t hold up quite so well out of context)—“I was adored once too” and “I’ll be revenged on the whole pack of you”—and the character of Feste the jester might be the greatest fool in Shakespeare. But lacking a better supporting cast, even the professional comedian in the play seems bored with his duty to mock the others. A greater subtitle for the play than “What You Will” is “If You Must.”
The Picture of Dorian Gray, By Oscar Wilde ❌
I still love this book. But reading it again felt unnecessary. The first time, I was so focused on the Lord Henry character, whom I admired for his wit at a time in my life when I thought that mattered more than anything else, that I didn’t really give too much attention to the other characters. But this supernatural story full of Poe-like horror wasn’t dull, even if I wasn’t enamored with Lord Henry during my second reading. The different layers of Wilde’s intelligence come through in how he was able to parody his public persona and explore friendship, vanity, aging, beauty, and a dark room full of more themes that course through this rather short but heavy novel. Although I’m content leaving this one closed and on my bookshelf, I still believe it is one of the most well-constructed and rewarding novels I’ve ever read.
If on a Winter’s Night a Traveler, By Italo Calvino ✅
Calvino’s story of you, the reader, trying to read his latest novel but having to go on an adventure just to find the right manuscript, and never finding the right manuscript, has so many layers and styles that it’s hard to really digest all of it in one go. The first read is more like a practice round, just a glance at all the various scenes Calvino has assembled—like being thrown into a room in an art museum that contains ten paintings done in very different styles and having to process them all while being marched through it by an impatient companion who won’t even give you enough time to read the informational cards next to each one. During my second read, I was better able to take each subplot one at a time and not worry that I was going to miss something crucial to the framing plot. I haven’t opened the book a third time, but I expect that I shall enjoy it more than the first or the second because I can better connect the large and the small pieces more aptly now that I am familiar with them. This, if I were to give one example other than Hamlet, is the most worthy story to read over and over again.