7 Life-Changing Essays Your Literary Bucket List Needs this Sunday Night

Because the word “essay” often evokes a sense of panic rooted in memories of five-paragraph nightmares, snooze-worthy classes, cranky teachers, and looming deadlines, many think it’s a form best kept in the classroom… As a result of this bad reputation, it’s possible you’ve excluded essays from your reading list. But I’m making the case that essays are the solution to your literary woes. Hear me out.
When the only thing longer than your to-do list is the novel on your bedside table, but you don’t want to settle for bad television, an essay will allow you to read something concise that’s also enriching and fun. Since sourcing this kind of reading material is a particularly tall order in the era of information overload, we’ve organized our reading list by mood. Scroll through my picks to choose pieces based upon your personal reading needs, whether you’re seeking motivation, laughter, or advice.

The Funny Tearjerker

This collection of essays borrows it’s title from Broder’s Twitter handle, and while it’s charming as a string of 140 character tweets, it’s even better in prose. At times heartbreaking and at others hilariously self-deprecating, Broder’s relentless bravery will make you laugh out loud while simultaneously shedding a tear (or ten). She’s especially honest and poignant in her writing on love and anxiety in the digital age, with “Honk if There’s a Committee in Your Head Trying to Kill You” and “Never Getting Over The Fantasy of You Is Going Okay.”

The Poetic Prose Master

Chills, I tell you, full body chills… This pick-me-up about connection, love, and longing is about to be your unofficial life coach. Brian Doyle opens his essay “Joyas Volardores,” with an obscure anecdote, inviting the reader to “consider the hummingbird for a long moment,” and ending with the reminder that “we all churn inside” and “live alone in the house of the heart.” He dazzles with themes so resonant and sentences so swift, they spill into each other to marry prose with poetry.

The Under-the-Radar Classic

I have a phobia of pigeons and other creatures with no sense of personal space, so when I read Maeve Brennan’s “The Long-Winded Lady” and came across the phrase, “I like pigeons,” I was sure her work wasn’t for me. However, I’m glad I read further because while we don’t see eye to eye on pigeons, she’s a downright amazing essayist. Cataloging her musings on the streets of New York City in 1970 for The New Yorker, she approaches writing with whimsy and wit. All of her essays are very impressionistic, so if you like reading about the ordinary moments in life to get a glimpse into something greater, you’ll love Brennan’s work. For example, “Bad Tiny,” a retelling of time when she meets a seriously annoying dog with an even more annoying owner, is a great exercise in writing as catharsis.

The Motivator

If you haven’t listened to David Foster Wallace deliver his speech “This is Water” at the 2005 Kenyon College graduation ceremony, make room in your pocket for the transcribed text because you’ll never want to part ways with it. At once brilliant and approachable without the pretension that’s been attributed to his other work, it’s an uplifting, quick, and fun read. I first encountered this essay while waiting in a two-hour line (in retrospect, I could’ve tackled his 1000-page novel Infinite Jest), which was fitting, as it encourages us to transform tedious tasks into opportunities to practice compassion with strangers, and ultimately ourselves.

The Thought Provoker

Talk about life-changing. “Islands,” an essay by the celebrated New Yorker critic Hilton Als, is the most impactful nonfiction prose of late. He is able to craft compelling narratives that are personal and transcendent, profound and digestible, especially in the form of an essay. Here’s a story about friendship, the way identity informs one’s sense of belonging, the subjectivity of memory, and the act of writing itself. Despite the complex issues it tackles, “Islands” is a quick read and one you’ll remember.

The Lighthearted Read

Sloane Crosley’s collection of essays “I Was Told There’d be Cake” is as funny as you’d expect it to be based upon her wry title. It’s hard to pick just one piece from this collection, as the book works so well cohesively. Crosley writes about being a young woman in New York City, touching on a wide variety of topics, from dating culture to personal quirks. Her voice is authentic and she never takes herself too seriously, so reading these essays will make you feel like you’re hanging out with an old friend.

The Nostalgic Brainteaser

It would be literary sacrilege to exclude this essayist from my list of must-reads. Joan Didion epitomizes California cool and is an icon in the fashion and publishing worlds alike, so if you aren’t familiar with her work, say goodbye to life as you know it (and if you’re going through a transition, “Goodbye to All That” is a great place to start). Her essays on the golden state are some of her best. She masterfully captures the tensions and intersections of dystopia and utopia in her seminal essay “Some Dreamers of the Golden Dream.” And if you’re fascinated by the Summer of Love, you should opt for her investigative piece on the culture of Haight-Ashbury in “Slouching Towards Bethlehem.”

What are you favorite essays? Share them with me in the comments so we can add them to our literary bucket lists!

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