I originally wrote this as a guest post on another blog, but I never posted it here.

The youngest of my three kids, a daughter navigating her junior year of college during this pandemic, is halfway to turning 21 as I write this. Which means we no longer have any teenagers in the family, let alone high school kids. I’m not really sure how that happened.

My wife and I are both readers, and we naturally shared books with all our kids from a young age. But there’s something special, downright sacred and altogether delightful, about sharing the perfect book with your kids when they’re in high school. That’s the age where, if you get lucky and choose wisely, if the stars align, the book and the child will connect in miraculous ways. It’s been my experience, at least, that some books we read in high school become touchstones, favorite texts we reread and treasure. This is not an exact science, every kid is different, and I certainly had some missfires. But when you get it right it’s uniquely satisfying.

Here are some of the books where I got it right.

CRUDDY by Lynda Barry

I said above that every kid is different, and not every book is right for every kid. Cruddy, an illustrated novel, is a case in point. Cruddy is not for the faint of heart. The story of Roberta Rohbeson, who lives in “the cruddy top bedroom of a cruddy rental house on a very cruddy mud road” is filled with horrific violence, rampant drug use, and pain. It’s also one of the most deeply humane, heartbreaking yet surprisingly hilarious, and truly original novels I’ve ever read. If you’ve ever read Barry’s weekly comic strip, Ernie Pook’s Comeek, then you can already guess that her illustrations enhance the story in brilliant and unexpected ways. For mature older teens.

BASTARD OUT OF CAROLINA by Dorothy Allison

Bastard Out of Carolina is basically fictionalized autobiography (her book Two or Three Things I Know for Sure covers the same material in a nonfiction format), and much like Cruddy, it deals with difficult subjects, including child abuse and incest. Set in Greenville, South Carolina in the 1950s, Bastard tells the sometimes harrowing, sometimes funny, and always moving story of Bone Boatwright as she navigates adolescence through troubling waters. Bone, a stand-in for Allison, is the kind of rare protagonist you will cry for, howl in rage for, and fall in love with. This book is sometimes hard to read, but Allison’s incandescent language never allows you to look away. Read this, and then read Two or Three Things I Know for Sure to meet the real people behind their fictional counterparts, photos included.

HIS DARK MATERIALS by Philip Pullman

This is my favorite fantasy trilogy of all time (sorry, Lord of the Rings) and I suggest it to pretty much everyone. Maybe you only know it from the not particularly good movie version of the first volume, The Golden Compass, or the better, recent Hulu adaptation. Maybe you’ve only read The Golden Compass, and not the other two volumes, The Subtle Knife and The Amber Spyglass. Here’s the thing—the trilogy gets better as it goes. By the end, it’s a complex examination of morality and religion, all wrapped up in some of the most beautiful fantasy world building ever commited to paper. Every character is memorable, every scene exquisitely rendered. There’s breathtaking adventure and genuine sorrow. Some readers have taken issue with Pullman’s treatment of organized religion, and I’ve seen charges of racism leveled concerning some characters. This is fertile ground for discussion, just one more reason I find the sharing of books so rewarding.

BOY’S LIFE by Robert McCammon

McCammon is known chiefly, I think, as a writer of intelligent thrillers and apocolyptic horror (Swan Song belongs on the same shelf with Stephen King’s The Stand). This is something else entirely—part murder mystery, part the exciting and sometimes dangerous adventures of a twelve year old boy and his friends in small town Alabama in the early 60s. Boy’s Life is infused with a childhood sense of wonder, nicely spiced with moments of magic realism. The reality of southern racism and poverty is not shied away from, but it’s tempered with a genuine but clear-eyed feel for life in that particular time and place. Quite simply, one of the best coming of age novels ever written.

EVERY HEART A DOORWAY by Seanan McGuire

By the time this novel came along, I only had one child still in high school, my youngest daughter. I handed it to her the moment I finished it. In Every Heart a Doorway, McGuire asks a deceptively simple yet profound question: What happens to all the children who enter portals to other worlds, and then come back? We’re introduced to Eleanor West’s School for Wayward Children, a sanctuary for those children whose parents don’t know how to deal with them, and to several of the kids now trying to make their way through our drab, dissapointing world after having left the magic behind. There are now five novels in the Wayward Children series, each one a small wonder of whimsical, ravishing storytelling.

BLOOD SPORT by Robert F. Jones

This one is a little different. Blood Sport was published in 1972, and a found a battered paperback copy a few years later, when I was in high school. It blew the top of my head clean off. Fast forward to my son’s high school years, and I couldn’t wait to share it with him, but…but, Blood Sport is extreme. It’s the fever-dream story of a father/son canoe trip down a mythological river, chocked full of magic realist imagery and audacious language, but also brutal violence, explicit sex, and some truly squirm-worthy scenes. The time had to be right. When he was sixteen, he and I joined his Scout troup for a father-son canoe trip on the French River delta in Canada, and I felt like the planets had alligned. It was indeed the perfect time.

BONUS: THREE RECENT BOOKS THAT ARE GREAT READS FOR HIGH SCHOOLERS

WANDERERS by Chuck Wendig

A big, meaty, doorstop of a novel, with big, meaty ideas. The story of a world-wide pandemic with echoes of The Stand and Swan Song, but very much its own thing. Heroic, flawed, altogether believable characters, and science that seems frightenly prescient.

GIDEON THE NINTH by Tamsyn Muir

I can’t really sum this novel up better than Charles Stross does in his cover blurb: “Lesbian necromancers explore a haunted gothic palace in space! Decadent nobles vie to serve the deathless Emperor! Skeletons!” Just to add—so many skeletons! A gonzo masterpiece.

WHEN WE WERE MAGIC by Sarah Gailey

When We Were Magic revolves around six female friends who all share the ability to do magic, and one boy who is dead, accidently, at the hands of one of those friends. Gailey excels at navigating the complexities of friendship, and her descriptions of how magic works are breathtaking.