#5onFri: Five Essay Collections to Check Out

by Lori Walker
published in Reading

Essays are having a hot moment right now, but they’ve been around for a long time. The word “essay” originates from the French word “essayer,” meaning “to try.” The form has certainly morphed with time, but in a sense boils down to the writer figuring out what they think and feel by writing about it. Also, I think it’s worth noting that while so-called “classic literature” has been dominated by old white dudes, this genre is squarely in the hands of women–and I love that!

Many of my favorite essay collections put a humorous spin on everyday life. I think finding the humor in the mundane is something we always need, but perhaps need a little bit more right now. Initially I thought this would be a pretty simple and straightforward assignment–pick five amazing collections of essays. Then I realized how hard it was to narrow it down to just five! So I hedged my bets on several of these.


1) Slouching Towards Bethlehem

Joan Didion. I love this woman. I named my cat Joan Didion and expect her to be called Joan Didion, not Joan. But that’s beside the point. Only not really because Didion is my favorite writer and she’s the first author I mention on this list.

This collection details Didion’s life in California during the 1960s. In her writing, she skillfully places herself front and center in the action, one of the first writers to begin doing so. Over her career, Didion has published several collections of essays and a few very powerful novels. I highly recommend her writing because she does a wonderful job of capturing the atmosphere of the setting she describes. 

2) Tiny Beautiful Things

Tiny Beautiful Things is a collection of self-help columns written by Cheryl Strayed. These columns first appeared as Dear Sugar on therumpus.net with Strayed’s identity unknown to readers, though she eventually had a coming out party.

This collection is absolutely beautiful and at times utterly gut-wrenching. Through her columns as Dear Sugar, Strayed not only answers the questions posed to her, but also the question behind what is actually asked. She infuses these columns with very personal stories from her own life–unusual for an advice columnist. All the while, she advocates for something called radical empathy. Her writing here elevates what could be a simple, rote advice column into a true work of art.

3) How to Be a Woman

Caitlin Moran is hilarious. This book is a mixture of memoir and manifesto on what it is like to be a woman nowadays. Each chapter tackles a different aspect of how to be a woman in the world. She does a great job of dismantling the outdated view of feminists as man-haters and makes something that is widely accessible. One of the biggest takeaways for me was that there isn’t a one-size-fits-all version of feminism, but the important thing is to support one another along the way.

Moran has published two other collections of essays that run the gamut from pop culture to politics to current events and everything in between. She’s also published two fantastic novels that do such a great job of depicting the growing process from teen to adult that I sincerely wish they had been around when I was 15.

4) I Was Told There’d Be Cake

The thing I love most about Sloane Crosley’s writing is how relatable it is to my life (and I think the lives of all women who were children in the 1980s and 1990s). She is a master at putting a humorous take on everything from the mundane to the unfortunate to the genuinely funny. To give you a sense, the first essay opens with the sentence: “As most New Yorkers have done, I have given serious and generous thought to the state of my apartment should I get killed during the day,” then goes on to detail her secret (embarrassing) collection of ponies and what she believes it says about her.

5) Calypso

David Sedaris’s writing is pretty much a guaranteed laugh-out-loud for anyone with even a smidgen of a sense of humor. He is a master at putting a hilarious spin on life. At times, critics have claimed that his writing blurs the line between fact and fiction. To that, I say that sometimes you can’t let all of the facts get in the way of a good story. Very rarely are you able to entertain by telling things exactly as they happened; sometimes you need to add a good twist or good line to make the story worth repeating.

Sedaris has written a number of essay collections–all of which I highly recommend. Calypso just happens to be his most recently published. He’s also begun publishing his diaries, which are a very interesting read because they give you the backstory to some of his essays.

Bonus: I just can’t help myself, so here’s some other essay collections you should check out (in no particular order): Dead Girls by Alice Bolin, How to Write an Autobiographical Novel by Alexander Chee, We Are Never Meeting in Real Life by Samantha Irby, Changing My Mind by Zadie Smith, and Recollections of My Nonexistence by Rebecca Solnit. I could go on and on–and I feel like I’m forgetting some very huge, very important collections–but I think this is a good starting point. Enjoy!

Lori Walker

Lori Walker is the Operations Maven at DIY MFA. Though she’s fallen off the wagon as a writer, she’s hoping to return to writing essays (perhaps even a novel!) through her involvement with DIY MFA. She also teaches yoga part-time in Smalltown, Oklahoma, where she lives with her husband and their cat, Joan Didion. You can follow her on Instagram at @LoriTheWriter.

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