6 Unpredictable Books Guaranteed to Make You Laugh

Juliet O'Connor
July 7 2023
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Nothing pairs better with a cathartically funny book than a belly laugh. As avid readers and bookworms, we often look for the right blend of wit, humor, and a dash of unpredictability to keep us engrossed. The books on this list are not just laugh riots but are also seasoned with emotional depth and heartfelt narratives that are sure to take you by surprise. So, get ready to indulge in stories that masterfully balance humor with sentiment, proving that sometimes the funniest tales can also be the most touching. Prepare to clutch your stomach, wipe away tears (of both laughter and emotion), and delve into a world of hilarity and heart.

Harold
by Steven Wright

HAROLD by legendary stand-up comedian Steven Wright is a delightfully amusing and profound journey into the mind of an average third grader as he navigates a single day at school in the 1960s. The story encapsulates the whimsical and often hilarious imaginings of Harold, from having coffee on the moon with Carl Sagan, to contemplating the birth of his future hearse driver. Readers will chuckle, ponder, and find themselves lost in Wright's uniquely surreal and vivid world. Heartfelt and hilarious, this book is filled with laughter, absurdity, and unexpected wisdom. It might just alter your daily perceptions in the most entertaining way.

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Harold
Steven Wright

A uniquely humorous and deeply profound novel from a legendary stand-up comedian that follows the thoughts of a 1960s third grader during a single day at school.

Steven Wright is one of the most significant and influential stand-up comedians in history. Rolling Stone ranked him fifteenth on their “50 Best Stand-ups of All Time” list, while the New York Times has written of his enduring legacy: “If you made a family tree of modern stand-up, he would top one of the few major and expanding branches. The children of Mr. Wright pack the comedy scene today.” Now comes his first novel, which is sure to be unlike anything you’ve ever read.

From the outside, Harold is an average seven-year-old third grader growing up in the 1960s. Bored by school. Crushing on a girl. Likes movies and baseball—especially the hometown Boston Red Sox. Enjoys spending time with his grandfather. But inside Harold’s mind, things are a lot more complex and unusual. His thoughts come to him as birds flying through a small rectangle in the middle of his brain. He visits an outdoor cafe on the moon and is invited aboard a spaceship by famed astronomer Carl Sagan. He envisions his own funeral procession and wonders if the driver of the hearse has even been born yet.

Harold documents the meandering, surreal, often hilarious, and always thought-provoking stream-of-consciousness ruminations of the title character during a single day in class. Saturated with the witticisms and profundities for which Wright’s groundbreaking stand-up has long been venerated, this novel will change the way you perceive your daily existence. To quote one of its many memorable lines: “Everything doesn’t have to make sense. Just look at the world and your life.”

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The Survivalists
by Kashana Cauley

THE SURVIVALISTS by Kashana Cauley is a compelling and riotously funny exploration of survival, both in its literal and metaphorical forms. The story follows Aretha, a driven Black lawyer who plunges into an offbeat world of doomsday prepping when she moves in with her boyfriend and his eccentric roommates. Cauley brilliantly intertwines dark humor with intense, topical questions about corporate success, gun ownership, and the socio-economic realities facing young Americans. With an uncanny balance between absurdity and profound insight, the narrative grips you, eliciting belly laughs one moment and deep introspection the next. A must-read that humanizes the bizarre, prompting you to question your notions of survival.

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The Survivalists
Kashana Cauley

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Swamp Story
by Dave Barry

Pulitzer Prize-winning author Dave Barry has done it again. SWAMP STORY is a wildly entertaining and uproariously funny Florida caper filled with eccentric characters, unexpected twists, and a uniquely Floridian brand of absurdity. Jesse, a broke mother trapped in the Everglades, discovers a treasure that could solve her problems, if only she can keep it away from dangerous treasure hunters. Meanwhile, a failing store owner hatches a viral social media scheme involving a faux monster and an alcoholic journalist in a Dora the Explorer mask. Barry's wry commentary on social media and celebrity culture is baked into this larger-than-life narrative, making it a laugh-out-loud romp through the Sunshine State that offers more than a few poignant insights along the way.

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Swamp Story
Dave Barry

Pulitzer Prize–winning New York Times bestselling author and actual Florida Man Dave Barry returns with a Florida caper full of oddballs and more twists and turns than a snake slithering away from a gator.

Jesse Braddock is trapped in a tiny cabin deep in the Everglades with her infant daughter and her ex-boyfriend, a wannabe reality TV star who turned out to be a lot prettier on the outside than on the inside. Broke and desperate for a way out, Jesse stumbles across a long-lost treasure, which could solve all her problems—if she can figure out how to keep it. The problem is, some very bad men are also looking for the treasure, and they know Jesse has it.

Meanwhile, Ken Bortle of Bortle Brothers Bait and Beer has hatched a scheme to lure tourists to his failing store by making viral videos of the “Everglades Melon Monster.” The Monster is in fact an unemployed alcoholic newspaperman named Phil wearing a Dora the Explorer costume head. Incredibly, this plan actually works, inspiring a horde of TikTokers to swarm into the swamp in search of the monster at the same time villains are on the hunt for Jesse’s treasure. Amid this mayhem, a presidential hopeful arrives in the Everglades to start his campaign. Needless to say, it does not go as planned. In fact, nothing in this story goes as planned. This is, after all, Florida.

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Farrell Covington and the Limits of Style
by Paul Rudnick

FARRELL COVINGTON AND THE LIMITS OF STYLE by Paul Rudnick is a richly layered, tragicomedy that spans half a century. The story chronicles the rule-defying romance between the irresistibly handsome and affluent Farrell Covington and Nate Reminger, a humble aspiring writer from New Jersey. As they traverse from Yale to global locales, navigating the tumultuous changes in society and the LGBTQIA+ movement, their love story becomes a poignant testament to enduring love amidst upheaval. Told with Rudnick's signature wit and insightful perception, this modern classic is a profound exploration of love, history, and the human spirit. It will make you laugh . . . and probably tear up as well.

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Farrell Covington and the Limits of Style
Paul Rudnick

“A case study in elegant, honest tragicomedy…by the genuinely hilarious Paul Rudnick” (Gary Shteyngart, New York Times bestselling author) that follows the decades-long, rule-breaking romance between the son of one of America’s wealthiest families and a middle-class aspiring author.

Devastatingly handsome and insanely rich, Farrell Covington is capable of anything and impossible to resist. He’s a clear-eyed romantic, an aesthete but not a snob, self-indulgent yet wildly generous. As the son of one of the country’s most powerful and deeply conservative families, the world could be his. But when he falls for Nate Reminger, an aspiring writer from a nice Jewish family in Piscataway, New Jersey, the results are passionate and catastrophic.

Together, the two embark on a unique romance that spans half a century. They are inseparable—except for the many years when they are apart. Moving from the ivy-covered bastion of Yale to New York City, Los Angeles, and eventually all over the world, Farrell and Nate experience the tremendous upheaval and social change of the last fifty years. From the freedom of gay life in 1970s Manhattan to the Hollywood closet, the AIDS epidemic, and the profound strides of the LGBTQ+ movement, this witty and moving novel shows how the world changes around us while we’re busy doing other things.

Written with “engaging wit, side-eyed perceptiveness, and barbed elan” (Michael Chabon), this modern classic proves that style has its limits, love does not.

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The Sweet Spot
by Amy Poeppel

Amy Poeppel’s THE SWEET SPOT is a tale of the unanticipated camaraderie that blossoms when an unexpected baby lands on the doorstep of a Greenwich Village brownstone. Lauren, Melinda, and Olivia find their lives interwoven in hilarious and heartwarming ways as they navigate through neighborhood feuds, unwanted viral fame, and sudden parenthood. Told with Poeppel's signature charm, wit, and delightfully quirky characters, this novel paints an endearing picture of unconventional families, friendships, and the pursuit of happiness in life's messiest moments. It's an enchanting read that serves up humor, heart, and a healthy dose of absurdity.

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The Sweet Spot
Amy Poeppel

Amy Poeppel brings her signature “big-hearted, charming” (The Washington Post) style to this wise and joyful novel that celebrates love, hate, and all of the glorious absurdity in between.

In the heart of Greenwich Village, three women form an accidental sorority when a baby—belonging to exactly none of them—lands on their collective doorstep.

Lauren and her family—lucky bastards—have been granted the use of a spectacular brownstone, teeming with history and dizzyingly unattractive 70s wallpaper. Adding to the home’s bohemian, grungy splendor is the bar occupying the basement, a (mostly) beloved dive called The Sweet Spot. Within days of moving in, Lauren discovers that she has already made an enemy in the neighborhood by inadvertently sparking the divorce of a couple she has never actually met.

Melinda’s husband of thirty years has dumped her for a young celebrity entrepreneur named Felicity, and, to Melinda’s horror, the lovebirds are soon to become parents. In her incandescent rage, Melinda wreaks havoc wherever she can, including in Felicity’s Soho boutique, where she has a fit of epic proportions, which happens to be caught on film.​

Olivia—the industrious twenty-something behind the counter, who has big dreams and bigger debt—gets caught in the crossfire. In an effort to diffuse Melinda’s temper, Olivia has a tantrum of her own and gets unceremoniously canned, thanks to TikTok.

When Melinda’s ex follows his lover across the country, leaving their squalling baby behind, the three women rise to the occasion in order to forgive, to forget, to Ferberize, and to track down the wayward parents. But can their little village find a way toward the happily ever afters they all desire? Welcome to The Sweet Spot.

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The Last Word
by Hanif Kureishi

A captivating journey into the world of a fading literary giant and his eager young biographer, THE LAST WORD by Hanif Kureishi delivers a compelling mixture of wit, warmth, and cutting-edge humor. It is centered around Harry, a budding writer, commissioned to pen an attention-grabbing biography about Mamoon Azam, an Indian-born writer in his twilight years, whose reputation and finances are in decline. Thrust into Mamoon's complex, surreal world, Harry quickly realizes that his subject is not as he seems. Expect battles of wits, insightful observations, and the poignant misery of outgrowing youthful exuberance in this humorous and moving novel.

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The Last Word
Hanif Kureishi

“Hanif Kureishi’s best novel since The Buddha of Suburbia” (The Independent, UK): a mischievous, wickedly funny, and intellectually deft story about a young biographer and the famous and reclusive novelist who is his subject.

Mamoon Azam is an eminent Indian-born writer who has made a career in England—but now, in his early seventies, his reputation is fading, his book sales are nonexistent, and the expensive habits of his flamboyant second wife are bleeding him dry. In a final attempt to revitalize his career, Mamoon’s publisher commissions Harry, an ambitious young writer, to produce a provocative biography to bring Mamoon back into the public eye.

Harry sets off for Mamoon’s estate, where he finds not the literary hero he had imagined, but a vain, bigoted, cynical, and cruelly manipulative genius, who quickly turns the tables on his ambitious young biographer. Harry must insinuate, seduce, and finesse the truth out of the extravagant and damaged characters in Mamoon’s surreal sphere as the young writer and the old master battle for the last word in the story of Mamoon’s life. Acute and brilliantly entertaining, The Last Word is a tale of youthful exuberance and the misery of outgrowing it, as hilarious as it is moving. It is Kureishi’s wisest work to date.

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Photo credit: iStock / demaerre

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