I am a terrible reader when it comes to children’s books. It’s not that I struggle to read in general or dislike reading to my kids in particular, the issue is that I have like zero resistance to anything even remotely tear-jerky. It’s not something I’m proud of, but give me a story where someone loses something, learns a lesson, or essentially does anything at all and suddenly I look like your mom watching the ending of “Beaches.”
So I invite you to laugh at my complete lack of machismo as I list the top children’s books that make me cry like a kid whose scoop of ice cream just fell off their cone and into a thresher.
“City Dog, Country Frog” by Mo Willems, illustrated by Jon J. Muth

Mo Willems, how dare you? At this point Willems has overthrown Dr. Suess as the grand emperor of grade school picture books, and even my emotional hair-trigger can get through “Elephant and Piggy” or “Don’t Let the Pigeon Drive the Bus” dry eyed (even though the poor pigeon is never going to get a chance to fulfill his lifelong dream of bus ownership, which is just…[sniff]…tragic).
Then out of left field all the lovable cartoonish characters are gone, replaced with page after page of beautiful watercolors about friendship and loss. Based on that heartwarming cover photo and the fact that I’ve described it as “Sad,” the plot points should be so obvious I hardly need to outline them, but just for full clarity they are:
A: Dog meets Frog.
B: Frog dies.
C: I cry like my genitals are caught in a laundry mangle.
To begin with, anything sad involving a dog gets exponentially sadder, and a cute puppy who, by coincidence, looks exactly like my dog only worsens the problem. Even the frog is somehow cute, and that’s really saying something since the standard look for frogs is “Damp pile of old pudding skins.” Seriously, look at these two:

That dog makes Lassie look like a pillowcase full of turds.
…and here’s City Dog coming to terms with Frog’s death a mere 7 sentences later.

I’M NOT CRYING; YOU’RE CRYING!
…Just kidding; I’m bawling my eyes out.
This little dude is in mourning by page 42. I didn’t need to look that number up; It’s burned into my mind like a glowing ember of sadness. I will think about him gazing forlornly across that frozen pond on my deathbed. Give me back that frog, Mo; I don’t need this kind of emotional catharsis when I’m trying to put a 5-year-old to bed.
“Oregon’s Journey” By Rascal, Illustrated by Louis Joos

This is such a sweet and sad celebration of America’s downtrodden I wouldn’t be surprised to find out that all the ink used in the printing process contained trace amounts of Woody Guthrie’s blood.
The plot involves Oregon the dancing circus bear who asks his friend, Duke the clown, to take him back to the forest to live with other bears. The circus seems to be in the middle of industrial Pittsburgh, and yeah: I’m right there with you, Oregon. If I were living in a grim caricature of the Rust Belt I think I’d want to move too.

“Take me home to the forest…or, like, literally anywhere else. At this point I’d settle for living in a highway median.”
Together they cross the country exclusively via transportation mentioned in Bob Dylan lyrics. They walk, ride a Greyhound bus, hitchhike, and jump an honest-to-god boxcar. No mention of them playing forlorn harmonica on the trip, but you’ve gotta assume.
On their way to the west coast they stay in rundown motels, sleep in an abandoned Chevy parked in a field, meet a traveling salesmen, a Navajo elder, an aspiring actresses, and MY GOD IS ANYTHING IN THIS BOOK NOT STRAIGHT OUT OF A FOLK SONG?!?!

Sing that paragraph over a G chord and you could probably get a headlining spot at the Newport Folk Festival.
Oregon’s Journey doesn’t leave me quite as emotionally drained as the other two entries on this list. I can make to the end glassy eyed with my voice breaking, but not quite ringing tears out my beard like it was a mop full of warm saline like the others. I can handle a bittersweet road trip way better than heartbroken dogs.
…I can also handle “Oregon’s Journey” a hell of a lot better than…
“The Velveteen Rabbit” by Margery Williams, illustrated by Charles Santore

Listen, Margery Williams, you Edwardian era jerk: I have young children, poor sleep, terrible personal habits, and one last fraying thread of emotional stability. I don’t need you tap-dancing all over it.
I don’t even know how I’m gonna write a few paragraphs about this thing. Just look at that picture up there. All I’ve done so far is look up a photo of the cover and I already need to go get a Gatorade because I’m dehydrated from dribbling 32 warm salty ounces of despair onto my shirt.
This is the 100 year anniversary of The Velveteen Rabbit, so at least I’m not alone. By now every parent alive has had to deal with this stupid, beautiful, heartwarming story about children bonding with stuffed animals. Your grandma was pulling for this adorable sack of sawdust to become a real rabbit back in the 60s. Her grandma was tearing up at it while tucking her own kids into bed in the 20s (presumably so they could be well rested for another big day at some factory that just made coal exhaust). The collective tears this book has rung out of parents could probably fill a pool deep enough to drown a giraffe.

Here’s the velveteen rabbit so sad it cries a single real tear and DEAR GOD WHY DID I GO LOOKING FOR A USABLE PHOTO FROM THIS BOOK?!
Look, I’m a grown man. I know toys don’t have thoughts or feelings, no matter how long and hard they’re loved. What I DO know, however, is that once my daughter outgrows her need for stuffed animals, I fully expect there be a day where I go out to the park near the house and see a grey and white cat walking around with a big red scarf on.
…because if my daughter’s favorite stuffy fails to make the cut, I am FINDING the Nursery Magic Fairy and that chick and I are gonna throw hands.
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