50 Funniest Books of All Time

COVER: PLUME; BACKGROUND: TWENTY20

Sometimes you want to delve into a serious, thought-provoking book that makes you question everything you’ve ever known about humanity. This is not one of those times. We present, in no particular order, books that are guaranteed to crack you up (and maybe make you pee your pants).

Cover: Back Bay Books; Background: Twenty20

1/50

Me Talk Pretty One Day by David Sedaris

Any of Sedaris’s hilarious books could’ve made this list, but this one’s titular story (about the author’s attempt to learn French after moving to Paris) puts it over the edge. Buy the book

Cover: Back Bay Books; Background: Twenty20

2/50

Bossypants by Tina Fey

Before she was Liz Lemon or Sarah Palin, Fey was a quirky kid from Pennsylvania who dreamed of becoming a comedian. Her book, about everything that happened in between, is incredible. Buy the book

Cover: Grove Weidenfeld; Background: Twenty20

3/50

A Confederacy of Dunces by John Kennedy Toole

Ignatius J. Reilly, a lazy eccentric who lives with his mother, is the unforgettable protagonist of this riotous book that was published posthumously by Toole’s own mother. (And won a Pulitzer. NBD.) Buy the book

Cover: Riverhead Books; Background: Twenty20

4/50

I Was Told There?d Be Cake by Sloane Crosley

Crosley’s debut essay collection is wry and witty about everything from horrendous first jobs to the Oregon Trail computer game. (Ford that river!) Buy the book

Cover: Plume; Background: Twenty20

5/50

You Can?t Touch My Hair by Phoebe Robinson

Proof you can be funny and inspiring? Robinson discusses serious issues like institutionalized racism and misogyny along with lighter ones like being U2’s biggest fan and her Magic Mike movie obsession. Buy the book

Cover: Ballantine; Background: Twenty20

6/50

The Witches of Eastwick by John Updike

The movie version is fabulous, but Updike’s original source material about three spurned women is even more satirical and wonderful. Buy the book

Cover: Back Bay Books; Background: Twenty20

7/50

Where?d You Go, Bernadette by Maria Semple

Bernadette is a reclusive architect and mother who goes missing. Her daughter tries to find her, compiling a funny portrait of a misunderstood woman along the way. Buy the book

Cover: Grand Central Publishing; Background: Twenty20

8/50

You?ll Grow Out of It by Jessi Klein

The head writer of Inside Amy Schumer muses on everything from being the adult version of a tomboy (a tom-man) to why some women are wolves and others are poodles. (We’ll let her explain.) Buy the book

Cover: Vintage; Background: Twenty20

9/50

I Feel Bad About My Neck by Nora Ephron

From one of our favorite writers of all time, a candid and dryly funny look at women who are aging and dealing with all the stuff that goes along with it. Buy the book

Cover: Picador; Background: Twenty20

10/50

The White Boy Shuffle by Paul Beatty

A scathingly funny debut novel about an awkward black surfer bum as he transforms from neighborhood outcast to basketball superstar to reluctant messiah. Buy the book

Cover: W.W. Norton & Company; Background: Twenty20

11/50

The Code of the Woosters by P.G. Wodehouse

The quintessential British humorist writes about Bertie Wooster and his valet Jeeves, as the latter saves the former from being arrested, lynched and accidentally engaged. Buy the book

Cover: Simon & Schuster; Background: Twenty20

12/50

The Comedy of Errors by William Shakespeare

The Bard’s slapstick farce is about two sets of twins who were separated at birth. Watching his hapless characters encounter each other through a series of escalating misunderstandings is a delight. Buy the book

Cover: Atria; Background: Twenty20

13/50

The Misadventures of Awkward Black Girl by Issa Rae

In this book named after her popular web series, Rae writes about what it’s like to balance being an introvert (read: kinda weird) with being black (read: supposed to be cool). Buy the book

Cover: Wordsworth Classics; Background: Twenty20

14/50

The Innocents Abroad by Mark Twain

Based on Twain's letters to newspapers about a voyage to Europe, Egypt and the Holy Land, The Innocents Abroad sharply critiques tourists who base their travels on guidebooks. (That’s not you, is it?) Buy the book

Cover: New York Review Books Classics; Background: Twenty20

15/50

Lucky Jim by Kingsley Amis

Jim Dixon is a lecturer at a fancy university. In this laugh-out-loud debut novel, Amis skewers the over-the-top English characters with whom Dixon interacts as he tries to hold on to his cushy job. Buy the book

Cover: CreateSpace Independent Publishing Platform; Background: Twenty20

16/50

Three Men in a Boat by Jerome K. Jerome

Despite being published in 1899, Jerome’s spectacularly comedic account of a three-man boat journey holds up shockingly well in 2017. Buy the book

Cover: Three Rivers Press; Background: Twenty20

17/50

Is Everyone Hanging Out Without Me? by Mindy Kaling

Working alternative title: 242 Pages That Will Make You Want to Become Mindy Kaling’s Best Friend. Buy the book

Cover: Vintage; Background: Twenty20

18/50

One More Thing by B.J. Novak

Speaking of Office alums, you know those random thoughts you have in the shower but quickly forget about? Novak has similar thoughts, but he turns them into short story gold. Buy the book

Cover: Del Rey; Background: Twenty20

19/50

The Hitchhiker?s Guide to the Galaxy by Douglas Adams

The first in a five-book trilogy (no, that’s not a typo), The Hitchhiker’s Guide is one of those rare science fiction-y books that pretty much every reader on earth can appreciate. Buy the book

Cover: Back Bay Books; Background: Twenty20

20/50

Scoop by Evelyn Waugh

A satire of sensationalist journalism and foreign correspondents, Scoop is partly based on Waugh’s experience working for the Daily Mail. Ooo, juicy. Buy the book

Cover: Harper Perennial; Background: Twenty20

21/50

The Bedwetter by Sarah Silverman

Candid, poignant and occasionally filthy, Silverman’s memoir covers everything from her childhood penchant for swearing to her unfortunate propensity for bed-wetting. Buy the book

Cover: Akashic Books; Background: Twenty20

22/50

Go the F**k to Sleep by Adam Mansbach

OK, you might not want to read this bedtime book to your toddler. But it’s profane, honest and really damn funny for adults. Buy the book

Cover: Grand Central Publishing; Background: Twenty20

23/50

I Like You by Amy Sedaris

You thought David was the only hysterical Sedaris? Nope. This offbeat guide to entertaining will have you rolling on the floor, then digging your Jell-O mold out of the garage. Buy the book

Cover: William Morrow Paperbacks; Background: Twenty20

24/50

Good Omens by Terry Pratchett and Neil Gaiman

This unlikely writing partnership produced an outlandish, fake-serious book about the birth of the son of Satan and the coming of the end of times. Buy the book

Cover: Dey Street Books; Background: Twenty20

25/50

Yes Please by Amy Poehler

This book has everything: a haiku about plastic surgery, a satirical birth plan, a brainstormed list of hypothetical books about divorce and tons more. Buy the book

Cover: Flatiron Books; Background: Twenty20

26/50

Furiously Happy by Jenny Lawson

A funny and tragic examination of her own severe depression, Lawson’s memoir makes light of mental illness without trivializing it. Buy the book

Cover: It Books; Background: Twenty20

27/50

Everything Is Perfect When You?re a Liar by Kelly Oxford

Twitter sensation Oxford chats like your funniest girlfriend about everything from throwing up on Chinese food deliverymen to stalking Leonardo DiCaprio. Buy the book

Cover: Allie Brosh; Background: Twenty20

28/50

Hyperbole and a Half by Allie Brosh

Born out of Brosh’s popular blog, this darkly funny book—illustrated with exaggeratedly childish drawings—tackles topics like the author’s depression and the “God of cake.” Buy the book

Cover: Scribner; Background: Twenty20

29/50

Sex, Drugs and Cocoa Puffs by Chuck Klosterman

Whether analyzing Saved by the Bell episodes or the artistic legacy of Billy Joel, Klosterman’s funny and discerning take on pop culture is completely one of a kind. Buy the book

Cover: St. Martin's Griffin; Background: Twenty20

30/50

John Dies at the End by David Wong

A sarcastic paranormal horror story, John Dies at the End is hard to describe, other than to say that it’s so weird that it somehow works. Buy the book

Cover: Mariner Books; Background: Twenty20

31/50

The Princess Bride by William Goldman

The love story of Westley and Buttercup is well known to anyone who can recite the movie line for line (guilty), but Goldman’s richly satirical original text shouldn’t be missed. Buy the book

Cover: Penguin Books; Background: Twenty20

32/50

Bridget Jones?s Diary by Helen Fielding

Same goes for Helen Fielding’s introduction to floundering 30-something Bridget Jones before she was made iconic by Renée Zellweger. Buy the book

Cover: Gallery Books; Background: Twenty20

33/50

The Girl with the Lower Back Tattoo by Amy Schumer

Schumer's first book doesn't disappoint, as the comic covers everything from dating a personal trainer who turns out to be a hoarder to how she's actually quite introverted. Buy the book

Cover: Puffin Books; Background: Twenty20

34/50

Pippi Longstocking by Astrid Lindgren

If you have kids, read this to them. If you don’t, reminisce over the outrageous adventures of this red-pigtailed heroine with a horse on her porch and a flair for the absurd. Buy the book

Cover: Harper Perennial; Background: Twenty20

35/50

Don Quixote by Miguel de Cervantes

Let’s bring it back to 1604, shall we? This timeless masterpiece tells the story of madman Don Quixote and his faithful squire, Sancho Panza, as they travel through 16th-century Spain. Buy the book

Cover: Grove Press; Background: Twenty20

36/50

How I Became a Famous Novelist by Steve Hely

Pete Tarslaw just wants a realistic amount of fame, financial comfort and to humiliate his ex-girlfriend at her wedding. How he does it makes for a superbly entertaining novel. Buy the book

Cover: Harper Perennial; Background: Twenty20

37/50

Bad Feminist by Roxane Gay

A self-professed feminist, Roxane Gay loves rap music. Including—especially, even—the aggressive, misogynistic kind. But that, she argues, doesn't mean she isn't a feminist. Rather, it means she's a bad one, and that's OK. Buy the book

Cover: Scribner; Background: Twenty20

38/50

Born Standing Up by Steve Martin

Before he was the star you know today, Steve Martin was a magician and Disneyland entertainer dipping his toe into comedy. This retelling of his pre-SNL days is fun and endearing. Buy the book

Cover: Riverhead Books; Background: Twenty20

39/50

The Brief Wondrous Life of Oscar Wao by Junot Diaz

Oscar is a nerdy, chubby Dominican kid from New Jersey who’s obsessed with science fiction and is terrified he’ll die a virgin. It’s probably more of a tragicomedy, but funny nonetheless. Buy the book

Cover: Penguin Books; Background: Twenty20

40/50

Money by Martin Amis

John Self is a commercial director who epitomizes the greed and lust of the 1980s. His misadventures and downward spiral would be depressing if Amis’s prose weren’t so darkly funny. Buy the book

Cover: Random House Trade Paperbacks; Background: Twenty20

41/50

Not That Kind of Girl by Lena Dunham

Dunham may not be the voice of her generation, but she's certainly a voice of a generation. She proves as much in this insightful collection about growing up and being a person in the world. Buy the book

Cover: Penguin Books; Background: Twenty20

42/50

Modern Romance by Aziz Ansari

Part humor, part sociological study, Ansari teamed up with NYU sociologist Eric Klinenberg to design a massive research project to study how love and relationships have changed with the times. Buy the book

Cover: Harper Perennial; Background: Twenty20

43/50

How to Be a Woman by Caitlin Moran

Moran is an unapologetic feminist, which is not—as she so delightfully proves in this book—mutually exclusive with being really (really) funny. Buy the book

Cover: Anchor; Background: Twenty20

44/50

Crazy Rich Asians by Kevin Kwan

Rachel visits Singapore for the first time with her ultra-wealthy boyfriend. What follows is a super fun romp complete with opulence, social climbing and sabotage (dun dun dun). Buy the book

Cover: Anchor; Background: Twenty20

45/50

Little Victories by Jason Gay

Gay, a newspaper columnist, wrote this book after his father was diagnosed with cancer. Never too earnest, he's always self-deprecating and wry. Buy the book

Cover: Villard; Background: Twenty20

46/50

I Love Everybody by Laurie Notaro

Some people console 20-somethings by saying life works itself out as you get older. Notaro doesn't. Instead she gripes about credit card debt, her canceled newspaper column, the evil moms at preschool and more. Buy the book

Cover: Back Bay Books; Background: Twenty20

47/50

Then We Came to the End by Joshua Ferris

A satire of the American workplace, Ferris's debut novel concerns the weirdly close bonds that form between people who see more of each other than they see their spouses, families and friends. Buy the book

Cover: BN Publishing; Background: Twenty20

48/50

Cold Comfort Farm by Stella Gibbons

Gibbons's 1932 book parodies the romanticized accounts of rural life that were popular at the time with the story of Flora Poste, an orphaned teenager who sets out to modernize her traditional town. Buy the book

Cover: Three Rivers Press; Background: Twenty20

49/50

How to Weep in Public ?by Jacqueline Novak

Novak’s hilarious and real approach to dealing with her depression is refreshingly frank, with lists like “Ways to avoid charming your therapist,” and “top four tips for crying in restaurants.” Buy the book

Cover: Simon & Schuster; Background: Twenty20

50/50

Catch-22 by Joseph Heller

Widely considered one of the most significant novels of the 20th century, Heller's WWII satire is about a group of airmen's repeated attempts to avoid combat missions that appear to lead to certain death. Buy the book

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The 50 Funniest Books We've Ever Read

Me Talk Pretty One Day by David Sedaris

Bossypants by Tina Fey

A Confederacy of Dunces by John Kennedy Toole

I Was Told There?d Be Cake by Sloane Crosley

You Can?t Touch My Hair by Phoebe Robinson

The Witches of Eastwick by John Updike

Where?d You Go, Bernadette by Maria Semple

You?ll Grow Out of It by Jessi Klein

I Feel Bad About My Neck by Nora Ephron

The White Boy Shuffle by Paul Beatty

The Code of the Woosters by P.G. Wodehouse

The Comedy of Errors by William Shakespeare

The Misadventures of Awkward Black Girl by Issa Rae

The Innocents Abroad by Mark Twain

Lucky Jim by Kingsley Amis

Three Men in a Boat by Jerome K. Jerome

Is Everyone Hanging Out Without Me? by Mindy Kaling

One More Thing by B.J. Novak

The Hitchhiker?s Guide to the Galaxy by Douglas Adams

Scoop by Evelyn Waugh

The Bedwetter by Sarah Silverman

Go the F**k to Sleep by Adam Mansbach

I Like You by Amy Sedaris

Good Omens by Terry Pratchett and Neil Gaiman

Yes Please by Amy Poehler

Furiously Happy by Jenny Lawson

Everything Is Perfect When You?re a Liar by Kelly Oxford

Hyperbole and a Half by Allie Brosh

Sex, Drugs and Cocoa Puffs by Chuck Klosterman

John Dies at the End by David Wong

The Princess Bride by William Goldman

Bridget Jones?s Diary by Helen Fielding

The Girl with the Lower Back Tattoo by Amy Schumer

Pippi Longstocking by Astrid Lindgren

Don Quixote by Miguel de Cervantes

How I Became a Famous Novelist by Steve Hely

Bad Feminist by Roxane Gay

Born Standing Up by Steve Martin

The Brief Wondrous Life of Oscar Wao by Junot Diaz

Money by Martin Amis

Not That Kind of Girl by Lena Dunham

Modern Romance by Aziz Ansari

How to Be a Woman by Caitlin Moran

Crazy Rich Asians by Kevin Kwan

Little Victories by Jason Gay

I Love Everybody by Laurie Notaro

Then We Came to the End by Joshua Ferris

Cold Comfort Farm by Stella Gibbons

How to Weep in Public ?by Jacqueline Novak

Catch-22 by Joseph Heller

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