The best devastatingly sad books that make you laugh out loud

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.

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. 

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? 

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!

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!