100 books like A Portrait of the Artist as a Young Man

Siddhartha is a profound exploration of spirituality, self-discovery, and the pursuit of meaning in life.

It encourages readers to seek their own paths, embrace the present moment, and develop a deep sense of interconnectedness with the world around them. The books protagonist Siddhartha encounters various forms of suffering throughout his journey, and he comes to recognize the necessity and inevitability of pain and hardship in life.

The novel teaches that true wisdom and growth can arise from embracing and accepting suffering rather than trying to escape or avoid it.

I encountered this book backward. As a teenager growing up at the end of the US war in Vietnam, I read the Mad magazine spoof of the movie version long before I saw the movie itself, and then I read the novel. I focused on the antiwar theme and the concern of the bomber crew to get home without getting shot down.

The novel was based on Heller’s wartime experience, but I hardly realized it was about bombing Italy until I discovered the papers one of his crewmates had donated to Cornell University. I learned how many of the episodes were based on real incidents, including the only time the novel focuses on Italian civilians—when the crew objects to destroying an Italian Alpine village of no military significance. 

I was twelve when I fell in love with the old fashioned allure of the 19th century that I discovered in this book, which provided an early template (1868), for generations of books to follow that break down female stereotypes.

I identified with different aspects of all four March daughters, but most powerfully with Jo, the writer, who secretively pursues publication, prevails as a successful author, and no doubt provided a template for my own development as a writer.

And Marmee’s nurturing model of mothering was especially consoling to me as I grew up entangled in a difficult mother/daughter relationship, later to be recycled in my own books.

While writing a paper about Douglass in graduate school in the 1990s, I learned that he had to overcome two obstacles to establishing an authentic voice in his own book.

First, abolitionists argued against slavery by claiming it dehumanized the slave. While that could be true, this theory could not account for charismatic Black writers like Douglass who were anything but dehumanized. Second, slave narratives in the antebellum era often followed a certain formula that limited the narrator’s originality.

In one striking passage in the Narrative, Douglass overcomes both restrictions by evoking an image of his body that offers visual testimony to creatively push back on these limiting conventions: “My feet have been so cracked with the frost [felt during cold nights during enslavement], that the pen with which I am writing might be laid in the gashes.”

One of my permanent, permanent favorites. Cather’s novel about a pair of French Catholic missionaries in 19th-century New Mexico is a lot of things: a portrait of a complex and life-giving friendship, a “loveship,” if I can borrow from Alice Munro.

It’s also an immersive historical treatment of Catholic proselytizing in the Southwest and a lyric poem about the beauty of that land. It’s smart about the rigors and consolations and the inevitable condescension of missionary work. It’s smart about everything. A perfect book.

I read A Little Princess when I was only ten, with no idea that it was a classic. All I knew was that I totally identified with Sarah, the protagonist, as she was buffeted by the vicissitudes of fortune. The issues of class portrayed in this book were already on my young mind, since I grew up in one of the poorest neighborhoods in the Bronx but also spent a lot of time in the wealthy environs of Manhattan and the contrast was immense. I was impressed by Sarah’s resilience and her ability to empathize with others in spite of the awful hand that had been dealt to her.

I strongly recommend this book as not only does it weave spooky images of ghostly events in one’s psyche, but couples it with fascinating phenomena such as telepathic communication and willpower. Furthermore, I was fascinated by the complex personality of the main protagonist, who allows himself to become victim of evil forces leading to a gradual descent into madness.

It also emphasises that social isolation in a remote place can have a detrimental impact on oneself and those close to you. I found the fight for survival in this tale riveting.

Although I have read a number of novels focused on friendship, this one stands out with particular vigor. It started the way I expected: two friends since childhood. The more I advanced into the reading, though, the more I perceived the two main characters—Elena and Lila—as the same person:  a sort of super-protagonist that incorporates not only the psychological traits of the two but their lives as well.

If it’s true that life is often a fight between who we are and who we would like to be, then this novel portrays that conflict masterfully. What I saw in this story, more than the recount of a friendship, is the power that lies hidden within each of us. Whether we annihilate it or let it bloom depends on the choices we make in our lives. 

So what if his worldview never makes sense to anyone but himself? I see Holden Caulfield as the quintessential benchmark for a bad boy, shucking off the last few days at the boarding school that expelled him to wander around Manhattan in a daze. Some readers don’t like him so much that they are personally invested in attacking him and what he represents. 

But what is it that he represents, exactly? When I look beyond the surface of his false bravado, he’s a character deeply affected by the death of his brother and is setting out on a quest to understand how to be a real person in a world of phonies. Many of us, as teenagers, also have moments of feeling misunderstood and alone. I know I did, and so did Holden. 

There is a purity and grace about this book that is deeply moving; it tells me about the love of a good man, as he explores his own life in the face of death. All he has to leave his small son is not money but the possibility of dedicating oneself to a good life.

It is set in middle America, in 1956, when I, as it happens, was ten years old. Everything that matters to me is captured here in this exquisite book. It is written beautifully, not ever weighed down by mind-numbing cliches. If only everyone would read this book, I thought as I sobbed my way through it, there would be no wars, and there would be time and inspiration for healing the planet. I take it with me wherever I go.