Funny and Heartbreaking the best kind
Discover the perfect blend of humor and heartache with our list of funny and heartbreaking books. These reads will make you laugh, cry, and everything in between.

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Slaughterhouse-Five
by Kurt Vonnegut
Kurt Vonnegut’s masterpiece, Slaughterhouse-Five is “a desperate, painfully honest attempt to confront the monstrous crimes of the twentieth century” (Time). Selected by the Modern Library as one of the 100 best novels of all time • One of The Atlantic’s Great American Novels of the Past 100 Years Slaughterhouse-Five, an American classic, is one of the world’s great antiwar books. Centering on the infamous World War II firebombing of Dresden, the novel is the result of what Kurt Vonnegut described as a twenty-three-year struggle to write a book about what he had witnessed as an American prisoner of war. It combines historical fiction, science fiction, autobiography, and satire in an account of the life of Billy Pilgrim, a barber’s son turned draftee turned optometrist turned alien abductee. As Vonnegut had, Billy experiences the destruction of Dresden as a POW. Unlike Vonnegut, he experiences time travel, or coming “unstuck in time.” An instant bestseller, Slaughterhouse-Five made Kurt Vonnegut a cult hero in American literature, a reputation that only strengthened over time, despite his being banned and censored by some libraries and schools for content and language. But it was precisely those elements of Vonnegut’s writing—the political edginess, the genre-bending inventiveness, the frank violence, the transgressive wit—that have inspired generations of readers not just to look differently at the world around them but to find the confidence to say something about it. Authors as wide-ranging as Norman Mailer, John Irving, Michael Crichton, Tim O’Brien, Margaret Atwood, Elizabeth Strout, David Sedaris, Jennifer Egan, and J. K. Rowling have all found inspiration in Vonnegut’s words. Jonathan Safran Foer has described Vonnegut as “the kind of writer who made people—young people especially—want to write.” George Saunders has declared Vonnegut to be “the great, urgent, passionate American writer of our century, who offers us . . . a model of the kind of compassionate thinking that might yet save us from ourselves.” More than fifty years after its initial publication at the height of the Vietnam War, Vonnegut’s portrayal of political disillusionment, PTSD, and postwar anxiety feels as relevant, darkly humorous, and profoundly affecting as ever, an enduring beacon through our own era’s uncertainties.


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Running with Scissors
by Augusten Burroughs
The author describes his bizarre coming-of-age years after his adoption by his mother's psychiatrist, during which he witnessed such misadventures as a fake suicide attempt and front-lawn family/patient sleepovers.
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A Heartbreaking Work of Staggering Genius
by Dave Eggers
NATIONAL BESTSELLER • PULITZER PRIZE FINALIST • A "A beautifully ragged, laugh-out-loud funny and utterly unforgettable book" (San Francisco Chronicle) that redefines both family and narrative. • From the bestselling author of The Circle. A Heartbreaking Work of Staggering Genius is the moving memoir of a college senior who, in the space of five weeks, loses both of his parents to cancer and inherits his eight-year-old brother. This exhilarating debut that manages to be simultaneously hilarious and wildly inventive as well as a deeply heartfelt story of the love that holds a family together.

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Everything Is Illuminated tie-in
by Jonathan Safran Foer
With only a yellowing photograph in hand, a young man -- also named Jonathan Safran Foer -- sets out to find the woman who may or may not have saved his grandfather from the Nazis. Accompanied by an old man haunted by memories of the war; an amorous dog named Sammy Davis, Junior, Junior; and the unforgettable Alex, a young Ukrainian translator who speaks in a sublimely butchered English, Jonathan is led on a quixotic journey over a devastated landscape and into an unexpected past. By turns comic and tragic, but always passionate, wildly inventive, and touched with an indelible humanity, this debut novel is a powerful, deeply felt story of searching: for the past, family, and truth.

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Catch-22
by Joseph Heller
Catch-22 is like no other novel. It is one of the funniest books ever written, a keystone work in American literature, and even added a new term to the dictionary. At the heart of Catch-22 resides the incomparable, malingering bombardier, Yossarian, a hero endlessly inventive in his schemes to save his skin from the horrible chances of war. His efforts are perfectly understandable because as he furiously scrambles, thousands of people he hasn't even met are trying to kill him. His problem is Colonel Cathcart, who keeps raising the number of missions the men must fly to complete their service. Yet if Yossarian makes any attempts to excuse himself from the perilous missions that he is committed to flying, he is trapped by the Great Loyalty Oath Crusade, the hilariously sinister bureaucratic rule from which the book takes its title: a man is considered insane if he willingly continues to fly dangerous combat missions, but if he makes the necessary formal request to be relieved of such missions, the very act of making the request proves that he is sane and therefore ineligible to be relieved. Catch-22 is a microcosm of the twentieth-century world as it might look to some one dangerously sane -- a masterpiece of our time.

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