The best books to make you laugh and think

Sean Silleck Author Of The End of Cake
By Sean Silleck

Who am I?

To me, humor is an essential ingredient, a vibrant medium in which anything can grow. I appreciate a good drama or tragedy as much as the next person, but at the end of the day, if a book doesn’t make me laugh, it won’t resonate. I also believe deeply in the concept of the human comedy. Or maybe I take this too literally. Either way, I consider the exploits of humans to be more often ridiculous than anything else. We are a pompous species and far less intelligent than we believe we are, and we deserve to be made fun of. Well, some of us do, anyway.


I wrote...

The End of Cake

By Sean Silleck,

Book cover of The End of Cake

What is my book about?

It’s the post-apocalypse, and one man, a baker named Pete, is all that stands between the return of civilization and the final destruction of humanity. To defeat the forces of darkness—the ignorance and selfishness of the anti-cakers—Pete must embark on a dangerous journey through the Wastes, a 2,000-mile expanse of apocalyptic awfulness, in order to find the last remaining hope for cake, a mythical baker named Betty. But does humanity’s salvation lie out there in the desolation or inside Pete’s own heart?

The books I picked & why

Shepherd is reader supported. We may earn an affiliate commission when you buy through links on our website. This is how we fund this project for readers and authors (learn more).

Skinny Dip

By Carl Hiaasen,

Book cover of Skinny Dip

Why this book?

I found Carl Hiaasen’s Skinny Dip while visiting my mother-in-law in Florida. The complex where she lived included a clubhouse that was always empty. Wandering into the small library one morning, my eyes gravitated immediately to Skinny Dip. In the very first paragraph, a woman is pushed from the deck of a cruise ship by her scheming husband. As she plunges toward the dark Atlantic, just off the Miami coast, she thinks, “I married an asshole.” Naturally, I was hooked and spent the next two hours reading half the book. I consider it a special piece of luck to have found Carl Hiaasen and his hilarious cast of Floridian degenerates, weasels, and idiots—and the minority of decent Floridians who must deal with them—while in their backyard. 

Skinny Dip

By Carl Hiaasen,

Why should I read it?

4 authors picked Skinny Dip as one of their favorite books, and they share why you should read it.

What is this book about?

Joey Perrone is a woman with a mission. She's just been pushed overboard from a cruise liner by Chaz, her scumbag husband, and survived to tell the tale. But rather than reporting him to the police, she decides to stay dead and - with a little help from her friends and a few of Chaz's enemies - instead of getting mad, she's going to get even.

Filled with a host of endearingly offbeat characters, and a narrative that is hilarious, romantic and thought-provoking by turns, Skinny Dip takes us on a journey through the warped politics of Southern Florida and…


A Clockwork Orange

By Anthony Burgess,

Book cover of A Clockwork Orange

Why this book?

Like a lot of people, I came to A Clockwork Orange after seeing Stanley Kubrick’s iconic adaptation, which cleverly incorporates elements of surreal humor into its many disturbing visuals. But the novel, with its groundbreaking use of an invented futuristic slang – Nadsat – is on another level in this regard. Despite the awful acts performed by Alex and his droogs, you can’t help laughing at such phrases as “bolshy groodies,” “starry vellochecks,” “pink glazzies,” and “a malenky bit bezoomny.” The language carries you creeching and smecking through the humble narrator’s descent into state-controlled redemption, all of it real horrorshow and full of joy joy joy, O My Brothers.

A Clockwork Orange

By Anthony Burgess,

Why should I read it?

13 authors picked A Clockwork Orange as one of their favorite books, and they share why you should read it.

What is this book about?

In Anthony Burgess's influential nightmare vision of the future, where the criminals take over after dark, the story is told by the central character, Alex, a teen who talks in a fantastically inventive slang that evocatively renders his and his friends' intense reaction against their society. Dazzling and transgressive, A Clockwork Orange is a frightening fable about good and evil and the meaning of human freedom. This edition includes the controversial last chapter not published in the first edition, and Burgess's introduction, "A Clockwork Orange Resucked."


End Zone

By Don DeLillo,

Book cover of End Zone

Why this book?

If you asked me to name Don DeLillo’s best novel, I would say White Noise. But if you asked me which is my favorite, I would say End Zone. Set in the burning endless space of West Texas, it follows the travails of the Logos College football team. The players are all exiles of one kind or another and find themselves in “the middle of the middle of nowhere, [a place] suggestive of the end of recorded time.” They spend their days crashing into each other at high velocity. Sometimes they fight. In the evenings they pray. DeLillo’s narrative roams the prairie like a tornado, spinning everything it touches into a dizzying mix of philosophy, religion, geopolitics, nuclear war, and of course football, that perfect metaphor for all human conflict, struggle, and joy. 

End Zone

By Don DeLillo,

Why should I read it?

2 authors picked End Zone as one of their favorite books, and they share why you should read it.

What is this book about?

The second novel by Don DeLillo, author of White Noise (winner of the National Book Award) and The Silence

At Logos College in West Texas, huge young men, vacuum-packed into shoulder pads and shiny helmets, play football with intense passion. During an uncharacteristic winning season, the perplexed and distracted running back Gary Harkness has periodic fits of nuclear glee; he is fueled and shielded by his fear of and fascination with nuclear conflict. Among oddly afflicted and recognizable players, the terminologies of football and nuclear war--the language of end zones--become interchangeable, and their meaning deteriorates as the collegiate year runs…


Gravity's Rainbow

By Thomas Pynchon,

Book cover of Gravity's Rainbow

Why this book?

Pynchon’s most famous tome is one of the 20th Century’s top literary heavyweights, up on the shelf next to Ulysses and To the Lighthouse, and I dove into it as an aspiring literato, eager to add it to my “conquered classics” list. But I was totally unprepared for the novel’s explosive humor. Still one of the funniest books I’ve ever read, it follows the main character, Tyrone Slothrop, through the ruins of war-ravaged Europe, from the rooftop banana farm in London during the V2 rocket attacks, to the Herman Goering Hotel and Casino on the newly liberated French Riviera, to the German rocket factories at Nordhausen, where we learn the secrets behind Dr. Laszlo Jamf’s diabolical Imipolex G. Along the way we meet Roger Mexico and Colonel Ernest Pudding, Darlene Quoad and Geli Tripping, Scorpia Mossmoon and Richard M. Zhlubb, to name a paltry few. Even Mickey Rooney shows up, selling hasish at the site of the 1945 Potsdam conference. Gravity’s Rainbow will blow your mind with the force of a V2 rocket, but you’ll be gut-laughing all the way to your obliteration. 

Gravity's Rainbow

By Thomas Pynchon,

Why should I read it?

5 authors picked Gravity's Rainbow as one of their favorite books, and they share why you should read it.

What is this book about?

Hailed by many as the major experimental nov el of the post-war period, Gravity''s Rainbow is a bizarre co mic masterpiece in which linguistic virtuosity creates a who le other world. '


Little Big Man

By Thomas Berger,

Book cover of Little Big Man

Why this book?

With great humor and deep empathy, Thomas Berger creates a vision of the Wild West not seen in any John Ford film. The eponymous hero journeys from his pioneer boyhood into the world of the Northern Cheyenne, who, despite slaughtering his family, adopt him as one of their own. There he learns their complicated ways. For example, “[While] Indians love war, … they don’t like to lose relatives to it. They really like one another in the same tribe, and while they hate their enemy, … they don’t want to change him into anything else.” Balanced between the Cheyenne and the ever-encroaching White Man, we travel headlong toward the last great showdown of the untamed West, on the banks of the Little Big Horn.

Little Big Man

By Thomas Berger,

Why should I read it?

5 authors picked Little Big Man as one of their favorite books, and they share why you should read it.

What is this book about?

'I am a white man and never forget it, but I was brought up by the Cheyenne Indians from the age of ten.' So starts the story of Jack Crabb, the 111-year old narrator of Thomas Berger's masterpiece of American fiction. As a "human being", as the Cheyenne called their own, he won the name Little Big Man. He dressed in skins, feasted on dog, loved four wives and saw his people butchered by the horse soldiers of General Custer, the man he had sworn to kill.

As a white man, Crabb hunted buffalo, tangled with Wyatt Earp, cheated Wild…


5 book lists we think you will like!

Interested in good and evil, quarterbacks, and magic-supernatural?

7,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about good and evil, quarterbacks, and magic-supernatural.

Good And Evil Explore 90 books about good and evil
Quarterbacks Explore 15 books about quarterbacks
Magic-Supernatural Explore 431 books about magic-supernatural

And, 3 books we think you will enjoy!

We think you will like VALIS, Crime and Punishment, and The Road if you like this list.