The best devastatingly sad books that make you laugh out loud

Who am I?

I have been teaching English for 25 years, both at the high school and middle school levels. And one thing I have seen in the lives of thousands of teenagers is that our days are filled with the most beautiful, amazing things, as well as the most devastating, tragic things. My own childhood was equal parts unconditional love and chaotic dysfunction. In fact, if life were a book, it would be on this list!

I wrote...

Jacked Up

By Erica Sage,

Book cover of Jacked Up

What is my book about?

It’s bad enough that Nick’s sister is dead and his parents are shipping him off to Jesus camp. He’s also being followed around by Jack Kerouac, who’s incredibly annoying for a genius. Nick’s pretty sure Eden Springs is going to drive him insane. The campers ride donkeys into the desert and replace song lyrics with Bible verses. Somehow, only Nick seems to find this strange.

Worst of all is the PC Box, into which the campers gleefully place prayers and confessions. Nick scribbles down his darkest secret—about his sister’s death—and drops it in the box. But then the box is stolen, with Nick’s secret inside of it. Nick is desperate to get the box back—before the world learns the truth about what he did. 
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The books I picked & why

Book cover of The Absolutely True Diary of a Part-Time Indian

Why did I love this book?

I shed tears about 16 times reading this book, half from laughing and half from crying. This book is about a Native American teenager, Arnold, who decides to move from his reservation school to the public school in his rural Washington town. His self-deprecating humor, which includes cartoons he draws, is laugh-out-loud funny. The reflections he shares about his family and his new classmates are absurd, as Arnold is the classic “I use humor to cope” kind of human. The Absolutely True Diary of a Part-Time Indian is full of hope, but the struggles he faces along the way are heart-breaking.

By Sherman Alexie,

Why should I read it?

2 authors picked The Absolutely True Diary of a Part-Time Indian as one of their favorite books, and they share why you should read it.

What is this book about?

Sherman Alexie tells the story of Junior, a budding cartoonist growing up on the Spokane Indian Reservation. Determined to take his future into his own hands, Junior leaves his troubled school on the rez to attend an all-white farm town high school where the only other Indian is the school mascot. Heartbreaking, funny, and beautifully written, The Absolutely True Diary of a Part-Time Indian, which is based on the author's own experiences, coupled with poignant drawings that reflect the character's art, chronicles the contemporary adolescence of one Native American boy as he attempts to break away from the life he…

Book cover of Me and Earl and the Dying Girl

Why did I love this book?

This book is awkward and sweary and absurd. I loved every page of it! Greg is a senior with only one friend and a mother who likes to set up playdates. For a high schooler. Super embarrassing. But, that’s how he meets Rachel! Sadly, she is dying of cancer. So, of course, this book is tragic! But Jesse Andrews has captured the teenage boy’s voice and phraseology, which made me laugh out loud. The added bonus is that Greg loves films (and I love films!), and he uses this talent to celebrate Rachel, who is – and this is not a spoiler because it’s in the title – dying. 

By Jesse Andrews,

Why should I read it?

2 authors picked Me and Earl and the Dying Girl as one of their favorite books, and they share why you should read it.

What is this book about?

Seventeen-year-old Greg has managed to become part of every social group at his Pittsburgh high school without having any friends, but his life changes when his mother forces him to befriend Rachel, a girl he once knew in Hebrew school who has leukemia. 25,000 first printing.

The Catcher in the Rye

By J.D. Salinger,

Book cover of The Catcher in the Rye

Why did I love this book?

This book changed my reading life forever. Catcher in the Rye was the first book I’d ever read narrated by a teenager. You see, back in the day, there was no such thing as Young Adult or Middle Grade (yes, I’m that old), so I read a lot of Stephen King, The Bible, and my mom’s leftover Harlequins. And then here comes the snarky Holden Caulfield, a kid who keeps flunking out of school while obsessing over the phoniness of everything the world has to offer. His observations are hilarious. And, anyway, who doesn’t love a book that was the most censored book in high schools for 21 straight years? 

By J.D. Salinger,

Why should I read it?

14 authors picked The Catcher in the Rye as one of their favorite books, and they share why you should read it.

What is this book about?

After leaving prep school Holden Caulfield spends three days on his own in New York City.

Looking for Alaska

By John Green,

Book cover of Looking for Alaska

Why did I love this book?

I have enjoyed every John Green book because each one makes me laugh and cry, but Looking for Alaska was his first novel. Maybe it was his best (it did win the Printz Award!), or maybe it was just my first time witnessing an author so eloquently balance grief, love, and humor, but I read Looking for Alaska in one sitting. The book features “Pudge”, who attends a boarding school (one of my favorite YA settings!), where he quotes famous last words and grapples with how and why his friend died, and if he is to blame for it. In the end, the beautiful, torturous truth is – we can never really know the answers. Ugh, just thinking about this book breaks my heart!

By John Green,

Why should I read it?

6 authors picked Looking for Alaska as one of their favorite books, and they share why you should read it.

What is this book about?

The award-winning, genre-defining debut from John Green, the #1 bestselling author of The Anthropocene Reviewed and The Fault in Our Stars

Winner of the Michael L. Printz Award • A Los Angeles Times Book Prize Finalist • A New York Times Bestseller • A USA Today Bestseller • NPR’s Top Ten Best-Ever Teen Novels • TIME magazine’s 100 Best Young Adult Novels of All Time • A PBS Great American Read Selection • Millions of copies sold!

First drink. First prank. First friend. First love.

Last words.

Miles Halter is fascinated by famous last words—and tired of his safe life…

Book cover of Please Ignore Vera Dietz

Why did I love this book?

I love everything A.S. King. She is my absolute favorite YA author. Her books are weird and thoughtful, and they stick in my head forever. Her award-winning Please Ignore Very Dietz is no different. Vera’s (former!) best friend Charlie has died. While she’s struggling with family stuff, and drinking stuff, and working at pizza place stuff, she’s being haunted by Charlie’s ghost who insists she tells the police what she knows. The story itself is quirky, and Vera’s narration is clever. And, then, of course, there’s a twist at the end! 

By A.S. King,

Why should I read it?

1 author picked Please Ignore Vera Dietz as one of their favorite books, and they share why you should read it.

What is this book about?

Vera’s spent her whole life secretly in love with her best friend, Charlie Kahn. And over the years she’s kept a lot of his secrets. Even after he betrayed her. Even after he ruined everything.
So when Charlie dies in dark circumstances, Vera knows a lot more than anyone—the kids at school, his family, even the police. But will she emerge to clear his name? Does she even want to?
Edgy and gripping, Please Ignore Vera Dietz is an unforgettable novel: smart, funny, dramatic, and always surprising.

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