I’VE ALWAYS LEANED INTO what’s funny about the terrible, in life and in my writing, in part as a coping mechanism, but also as a way to bring people in. If things are just across-the-board awful, it’s my experience that people stop listening and/or reading. They turn away, back to the safe mundane. But aptly placed humour can return the humanity to the situation and remind the reader that we’re all in this together. It can give comfort and relief, but also a new way of looking at a situation. It can open up an opportunity for psychological insight and stop a piece of writing from becoming a one-note downer.
These ten books are perfect for when you’re going to either cry or laugh, so you might as well laugh…

Rabbits for Food by Binnie Kirshenbaum
This is a novel about a middle-aged woman who suffers from depression and ultimately has a breakdown that lands her on a psych ward. Which doesn’t sound funny, but the narrator, Bunny, is such an astute and wry observer of her life, that this truly is a laugh-out-loud (and then cry into pillow) kind of book.

Nothing to See Here by Kevin Wilson
Lillian, a woman who for sure doesn’t have her own life together, ends up as the nanny for two kids who (occasionally) burst into flames. Don’t worry – the fire doesn’t hurt them, but it’s pretty inconvenient. What I love so much about this book is how much Lillian cares and wants to problem-solve the fires, not just put them out. Not to make too fine a point of it, but it’s what she can’t do with her own life. That’s a heavy-handed review for a book that isn’t heavy-handed at all.

Dept. of Speculation by Jenny Offill
Offill’s novel-in-flash is about the end of a marriage, which is of course not funny. But the narrator’s short, pithy observations are hilarious. There are so few words in this novel that it has the illusion of being a quick bite of a read, but that’s the brilliance of it.

Catch-22 by Joseph Heller
A classic, and a worthy one. This takes place near the end of World War II. Bomber Yossarian has choices, sort of, but none of them are good and everything that might save him might also kill him.

Dear Committee Members by Julie Schumacher
I deeply admire an epistolary novel, especially one that isn’t dry. Professor Jason Fitger’s life is a mess, and yes he’s constantly being asked to write letters of recommendation. Which he does, much to the readers’ delight.

Eleanor Oliphant is Completely Fine by Gail Honeyman
Eleanor is frank and socially awkward and keenly self-aware of her faults. A friendship that turns into love and a revelation at the end turn this into more of a cry than a laugh kind of book, but there are still a lot of funny moments throughout.

Touch by Courtney Maum
Trend forecaster Sloane Jacobsen is all about technology and one hundred percent not about feelings. But as her own life gets weirder and weirder (hello, boyfriend in an impenetrable bodysuit), she begins to long for, well, touch.

Summer House with Swimming Pool by Herman Koch
This one lands more on the dark side of darkly funny. A physician tries to explain and defend the medical mistake that led to a famous actor’s death, which, it turns out, might not have been an accident at all. It’s the psychological observations that really land and cause that laugh-cringe throughout this book.

Joan is Okay by Weike Wang
Joan is an ICU doctor in her thirties. She’s the daughter of Chinese parents and she’s successful and she certainly thinks she’s okay. Joan is so unself-aware, so wrapped up in meeting all the expectations she thinks everyone has of her, that it’s impossible not to love her.

Fight Night by Miriam Toews
Swiv is nine. Her mother is pregnant and her grandmother, who is in theory taking care of Swiv, is frail and eccentric. When Grandma decides to take Swiv on a road trip, the adventure really begins. Miriam Toews can do no wrong as far as I’m concerned. Her level of empathy for her characters, her tender and astute observations about life, and her very gentle fun-poking at all of it make this one of the best books I’ve ever read.

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Jen Dupree is an assistant editor for The Masters Review, a librarian, and a former bookstore owner. Her work has appeared in December, Solstice, The Masters Review, On the Rusk and other notable places. Her novel The Miraculous Flight of Owen Leach was published in April 2022 by Apprentice House Press. Her second novel, What Do You Want from Me? is due out in the spring of 2025.
jenniferdupree.com
mastersreview.com
@writerjendupree

Author photo by Sarah Copperberg