6 Tragicomedy Books That’ll Give You Emotional Whiplash

May 30 2023
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Whenever someone asks me what my favorite type of book is I typically tell them: “The ones that make me laugh and cry within the same sitting.” What kind of masochism is this, you ask? That would, of course, be the genre known affectionately as the tragicomedy, in which a work of fiction contains elements of both tragedy and comedy—be it comic relief to lighten an especially depressing plotline or a surprisingly happy ending for a character after an otherwise unhappy set of circumstances.

Either way, tragicomedies are anything but boring. With sudden twists and turns that pull on your heartstrings and tickle your funny bone, this genre of work gives you emotional whiplash— keeping you in the moment for many dramatic happenings.

Calling Ukraine
by Johannes Lichtman

An American moves to Ukraine to teach customer service agents how to make small talk. Sounds like a comedy, doesn’t it? Well, that’s exactly how Johannes Lichtman’s CALLING UKRAINE starts out. Thirty-year-old John Turner seeks to escape from a recent stateside break-up and family death and travels to Ukraine to accept a friend’s unusual job offer. As he’s introduced to cultural customs, John begins to find his place among his “employees,” including one woman he’s immediately attracted to. As a romantic entanglement ensues, the fun-loving, goofy, character-driven plot is derailed by an undeclared Russian attack and act of domestic violence that John continually overhears next door. Unsure what to do and how to prevent the suffering of those nearest to him, John must make a bold choice. Painfully relevant to current global affairs, this pure tragicomedy is worth every tear.

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Calling Ukraine
Johannes Lichtman

National Book Foundation 5 Under 35 honoree and author of Such Good Work Johannes Lichtman returns with a novel that is strikingly relevant to our times—about an American who takes a job in Ukraine in 2018, only to find that his struggle to understand the customs and culture is eclipsed by a romantic entanglement with deadly consequences.

Shortly after his thirtieth birthday, John Turner receives a call from an old college friend who makes him an odd job offer: move to Ukraine to teach customer service agents at a startup how to sound American. John’s never been to Ukraine, doesn’t speak Ukrainian, and is supposed to be a journalist, not a consultant. But having just gone through a break-up and the death of his father, it might just be the new start he’s been looking for.

In Ukraine, John understands very little—the language and social customs are impenetrable to him. At work, his employees are fluent in English but have difficulty grasping the concept of “small talk.” And although he told himself not to get romantically involved while abroad, he can’t help but be increasingly drawn to one of his colleagues.

Most distressing, however, is the fact that John can hear, through their shared wall, his neighbor beating his wife. Desperate to help, John decides to offer the neighbor 100,000 hryvnias to stop. It’s a plan born out the best intentions, but one that has disastrous repercussions that no amount of money or altruism can resolve.

Like Ben Lerner’s Leaving the Atocha Station and Garth Greenwell’s What Belongs to You, Calling Ukraine reimagines the American-abroad novel. Moving effortlessly between the comic and the tragic, Johannes Lichtman deploys his signature wry humor and startling moral acuity to illuminate the inevitable complexities of doing right by others.

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All My Puny Sorrows
by Miriam Toews

The story of two sisters, ALL MY PUNY SORROWS explores the bonds of family, even through times of death and darkness. Elfrieda is a world-renowned concert pianist cursed with the same devastating depression that her father endured until his eventual suicide. She’s a highly intelligent, creative genius who also happens to be eager to take her own life. Luckily for her, her sister Yolandi is a steady presence in her life and has been for decades, dissuading—and outright stopping—her from succumbing to her suicidal tendencies. Whereas Elf’s life is filled with pain, Yolandi’s is ever-amusing as she writes novels, sleeps with various men, and seeks to entertain her teenage kids. Truly the comic relief in this tragicomedy, Yolandi faces her family’s tragedies with a smile and witty jokes. Miriam Toews’s powerful work is a testament to sisterhood and its ability to overcome life’s sorrows.

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All My Puny Sorrows
Miriam Toews

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Everyone in This Room Will Someday Be Dead
by Emily Austin

Riddled with anxiety and seeking relief, an atheist lesbian named Gilda arrives at a Catholic church that is advertising free mental health services. But when she arrives, the church’s head priest mistakes her for a job applicant for the recently open position of church receptionist.  Gilda, too embarrassed to correct him, accepts the job offer only to become fixated on her predecessor who mysteriously died. When she begins an email correspondence with that receptionist’s friend, Gilda is forced to impersonate this deceased woman while also pretending to be a good Catholic. Throughout this tragicomedy, Gilda continues to dwell on death in hilarious monologues that are only interrupted when the police begin to investigate the previous receptionist’s passing. Dark comedy at its best, EVERYONE IN THIS ROOM WILL SOMEDAY BE DEAD features a hilarious main character in the most tragic of circumstances.

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Everyone in This Room Will Someday Be Dead
Emily Austin

In this “fun, page-turner of a novel” (Sarah Haywood, New York Times bestselling author) that’s perfect for fans of Mostly Dead Things and Goodbye, Vitamin, a morbidly anxious young woman stumbles into a job as a receptionist at a Catholic church and soon finds herself obsessed with her predecessor’s mysterious death.

Gilda, a twenty-something, atheist, animal-loving lesbian, cannot stop ruminating about death. Desperate for relief from her panicky mind and alienated from her repressive family, she responds to a flyer for free therapy at a local Catholic church, and finds herself being greeted by Father Jeff, who assumes she’s there for a job interview. Too embarrassed to correct him, Gilda is abruptly hired to replace the recently deceased receptionist Grace.

In between trying to memorize the lines to Catholic mass, hiding the fact that she has a new girlfriend, and erecting a dirty dish tower in her crumbling apartment, Gilda strikes up an email correspondence with Grace’s old friend. She can’t bear to ignore the kindly old woman who has been trying to reach her friend through the church inbox, but she also can’t bring herself to break the bad news. Desperate, she begins impersonating Grace via email. But when the police discover suspicious circumstances surrounding Grace’s death, Gilda may have to finally reveal the truth of her mortifying existence.

With a “kindhearted heroine we all need right now” (Courtney Maum, New York Times bestselling author), Everyone in This Room Will Someday Be Dead is a crackling and “delightfully weird reminder that we will one day turn to dust and that yes, this is depressing, but it’s also what makes life beautiful” (Jean Kyoung Frazier, author of Pizza Girl).

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Quicksand
by Steve Toltz

Some of the best tragicomedies are dark satires that strive to unpack our society’s absurdities. QUICKSAND is one such work of fiction. Two lifelong friends, Liam and Aldo, have known each other since high school, initially forming a bond after both lost sisters at an early age. As they grow, they find separate paths. Liam is a cop and aspiring novelist while Aldo is a struggling entrepreneur with each of his latest ventures ending in disaster—including his marriage. Liam believes that Aldo’s misfortunes may be a writing opportunity, especially as Aldo seeks to win back his ex-wife who recently had a baby with another man. Offering hilarious commentary on some seriously dark subject matter, author Steve Toltz explores the hypocrisy of modern society and the pain associated with it by infusing comedy at every turn. The definition of a tragicomedy, this book will have readers laughing one minute and crying the next.

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Quicksand
Steve Toltz

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Hark
by Sam Lipsyte

A daring work that looks to answer some of life’s biggest questions, HARK finds failed stand-up comedian Hark Morner just as he begins his new career as a new-age guru. Blending elements of mindfulness with visualization and even revisionist history, Hark takes on the problems of a cast of eccentric characters all in desperate need of finding focus. Mostly centered on Fraz Penzig and his failing marriage to Tovah, this book outlines the great distances people will go to believe in something even as the end of our world becomes more and more inevitable. While Hark himself is a tragic figure that relies on a twisted (albeit laugh out loud) outlook it really is the circle of sad figures that surround him that make this social satire so gripping. Prepare to be entertained by the terrible situations we sometimes encounter in this one-of-a-kind novel.

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Hark
Sam Lipsyte

An “extremely funny...brilliantly alive” (The New York Times Book Review) social satire of the highest order from bestselling author Sam Lipsyte, centered around an unwitting mindfulness guru and the phenomenon he initiates.

In an America convulsed by political upheaval, cultural discord, environmental catastrophe, and spiritual confusion, so many of us find ourselves anxious and distracted, searching desperately for peace, salvation, and—perhaps most immediately—just a little damn focus. Enter Hark Morner, a failed stand-up comic turned mindfulness guru whose revolutionary program is set to captivate the masses. But for Fraz and Tovah, a middle-aged couple slogging through a very rough patch, it may take more than the tenets of Hark’s “Mental Archery” to solve the riddles of love, lust, work, and parenthood on the eve of civilizational collapse. And given the sudden power of certain fringe players, including a renegade Ivy League ethicist, a gentle Swedish kidnapper, a social media tycoon with an empire on the skids, and a mysteriously influential (but undeniably slimy) catfish, it just might be too late. But what’s the point of a world, even a blasted-out post-apocalyptic world, if they don’t try with all their might to keep their marriage alive?

In this “awfully funny...tartly effective sendup of 21st-century America” (Star Tribune, Minneapolis) Sam Lipsyte reaches new peaks of daring in a novel that revels in contemporary absurdity and the wild poetry of everyday language while exploring the emotional truths of his characters. “Recommended reading” (Vanity Fair), in which “every line feels as thrillingly charged as a live wire” (O, The Oprah Magazine), Hark is a smart, incisive look at men, women, and children seeking meaning and dignity in a chaotic, ridiculous, and often dangerous world.

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Tracy Flick Can't Win
by Tom Perrotta

You can’t say “satire” without thinking about the bestselling author Tom Perrotta, who has dedicated his career to writing wholly American stories that place oddball characters in unconventional situations. TRACY FLICK CAN’T WIN is no different. Featuring the iconic main character from his book ELECTION, his latest book finds Tracy as the soon-to-be principal at a New Jersey high school—if she can align herself with a tech millionaire’s scheme to create a Hall of Fame for the school. The hopeful first inductee is former football player, Vito Falcone. His troubled life makes him a controversial selection, and leads to a schoolwide debate that forces a cast of dubious characters into Tracy’s orbit. As sharp as any Perrotta novel, this book takes on serious topics and injects dark humor into each of them. It’s the kind of emotional whiplash that will leave you out of breath by the final pages.

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Tracy Flick Can't Win
Tom Perrotta

Soon to be a major motion picture starring Reese Witherspoon

“Tom Perrotta is…one of the great writers that we have today. I love this book.” —Harlan Coben

An “engrossing and mordantly funny” (People) novel about ambition, coming-of-age in adulthood, and never really leaving high school politics behind—featuring New York Times bestselling author Tom Perrotta’s most iconic character of all time.

Tracy Flick is a hardworking assistant principal at a public high school in suburban New Jersey. Still ambitious but feeling a little stuck and underappreciated in midlife, Tracy gets a jolt of good news when the longtime principal, Jack Weede, abruptly announces his retirement, creating a rare opportunity for Tracy to ascend to the top job.

Energized by the prospect of her long-overdue promotion, Tracy throws herself into her work with renewed zeal, determined to prove her worth to the students, faculty, and School Board, while also managing her personal life—a ten-year-old daughter, a needy doctor boyfriend, and a burgeoning meditation practice.

But nothing ever comes easily to Tracy Flick, no matter how diligent or qualified she happens to be. Her male colleagues’ determination to honor Vito Falcone—a star quarterback of dubious character who had a brief, undistinguished career in the NFL—triggers memories for Tracy and leads her to reflect on the trajectory of her own life. As she considers the past, Tracy becomes aware of storm clouds brewing in the present. Is she really a shoo-in for the principal job? Is the Superintendent plotting against her? Why is the School Board President’s wife trying so hard to be her friend? And why can’t she ever get what she deserves?

A sharp, darkly comic, and pitch-perfect chronicle of the second act of one of the most memorable characters of our time, Tracy Flick Can’t Win “delivers acerbic insight about frustrated ambition” (Esquire).

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Photo credit: iStock / Tetiana Soares

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