The best funny books about serious subjects

The Books I Picked & Why

A Confederacy of Dunces

By John Kennedy Toole

Book cover of A Confederacy of Dunces

Why this book?

The hyperintelligent and dysfunctional 30-year-old protagonist of this novel lives with his mother in New Orleans and is obsessed with all things medieval.  He has picaresque adventures in the French Quarter.  The novel is laugh-out-loud funny and yet poignant—something I strive for as a writer of tragicomedy.  My novel is similarly steeped in a place—those grieving engage in a process of cementing associations to the lost loved one, and those referents are often tied to the shared spaces they inhabited together.  


When you buy a book we may earn a small commission.

The Magic Kingdom

By Stanley Elkin

Book cover of The Magic Kingdom

Why this book?

Eddy Bale becomes a crusader for children after the death of his own young son and decides to take a group of terminally ill children to Disneyland for a holiday. The antic hyperbolic tone of the narration is utterly at odds with the grave subject matter and the novel is as hilarious as it is heartbreaking.  


When you buy a book we may earn a small commission.

Slaughterhouse-Five

By Kurt Vonnegut

Book cover of Slaughterhouse-Five

Why this book?

In this iconic semiautobiographical war novel, the narrator struggles with how to recount his experiences during the bombing of Dresden, adopting the guise of the time-traveling Billy Pilgrim to tell his story.  Decades on, the novel is as timely and poignant as ever; a forerunner of the trauma narrative; a book that, better than any other I can think of, conveys what it is like to suffer from PTSD—events so horrifying that one can only “cope” (if that is the right word) by means of psychic feints and dissociative logic. The novel is supremely funny; the author has a gift for underscoring horror with pellucid description.    


When you buy a book we may earn a small commission.

Oblivion: Stories

By David Foster Wallace

Book cover of Oblivion: Stories

Why this book?

DFW’s hyperbolic virtuosity is on display in this collection of stories about fakery, imposterdom, trauma, and the nature of consciousness, of which Good Old Neon, the monologue of a salesman who traffics in fakeries, is the showstopper.  DFW knew depression well as he did psychopharmacology and rehab and our mental health apparatus—his work is imbued with the details of these worlds and he conveys possibly better than any other what it is like to be trapped in a depressed, quizzical mind.  The collection is a moving and hilarious tour-de-force.


When you buy a book we may earn a small commission.

Mostly Dead Things

By Kristen Arnett

Book cover of Mostly Dead Things

Why this book?

This book is a more recent addition to the oeuvre of grief tragicomedy. In the novel, a third-generation taxidermist deals with the aftermath of her father’s suicide. The details are hilarious—lots of minutia about the family business—but the book is also heartbreaking, as Jessa tries to hold herself and her family together in the wake of her father’s sudden demise.  The novel, both morbid and irreverent, tackles themes of death, preservation, and how we honor those who have passed.   


When you buy a book we may earn a small commission.

Closely Related Book Lists

Distantly Related Book Lists