UPDATE: Since this piece was originally published in 2015, more lovely additions to this small, sweet canon have been born: Jerome by Heart, Julián Is a Mermaid, and Happy Birthday, Alice Babette.

“This is the entire essence of life: Who are you? What are you?” the young Leo Tolstoy wrote in his journal of selfhood. The quest for an answer begins as soon as we develop theory of mind as children — usually around the age of four or five — and continues until we dissolve back into stardust. We inherit part of our individual answers from our parents and our culture, in traits passed down via DNA and beliefs synthesized from societal norms, but must contend with the remaining parts on our own. In his magnificent meditation on identity, Andrew Solomon offers a useful distinction between these two answer-sources, calling the inheritable part “vertical identity” and the self-invented part “horizontal identity.” The process of answering this existential question is challenging enough for any human being, increasingly so the further one’s sense of identity falls from a cultural norm. It is especially arduous for the young, the different, and most of all the very young who feel very different.

Gathered here is a selection of intelligent, imaginative, and deeply assuring children’s books for little humans anxious or anguished by their particular point of difference — loving or identifying with a gender other than the one society has prescribed for them to love or be. Vintage and modern, these books dance across the spectra of the playful and the poignant, the sincere and the subversive, the personal and the political.

WE ARE ALL IN THE DUMPS WITH JACK AND GUY

The 1993 masterwork We Are All in the Dumps with Jack and Guy (public library), which I’ve covered extensively here, is the darkest yet most hopeful book Maurice Sendak ever created, as well as one of his most personal. It’s an unusual fusion of two traditional Mother Goose nursery rhymes — “In the Dumps” and “Jack and Gye” — reimagined and interpreted by Sendak’s singular sensibility, and permeated by many layers of cultural and personal subtext.

On a most basic level, the story follows a famished black baby, part of a clan of homeless children dressed in newspaper and living in boxes, kidnapped by a gang of giant rats. Jack and Guy, who are strolling nearby and first brush the homeless kids off, witness the kidnapping and set out to rescue the boy. But the rats challenge them to a rigged game of bridge, with the child as the prize. After a series of challenges that play out across a number of scary scenes, Jack and Guy emerge victorious and save the boy with the help of the omniscient Moon and a mighty white cat that chases the rats away.

Created at the piercing pinnacle of the AIDS plague and amid an epidemic of homelessness, it is a highly symbolic, sensitive tale that reads almost like a cry for mercy, for light, for resurrection of the human spirit at a time of incomprehensible heartbreak and grimness. It is, above all, a living monument to hope — one built not on the denial of hopelessness but on its delicate demolition.

But the book’s true magic lies in its integration of Sendak’s many identities — the son of Holocaust survivors, a gay man witnessing the devastation of AIDS, a deft juggler of darkness and light.

Jack and Guy appear like a gay couple, and their triumph in rescuing the child resembles an adoption, two decades before that was an acceptable subject for a children’s book. “And we’ll bring him up / As other folk do,” the final pages read — and, once again, a double meaning reveals itself as two characters are depicted with wings on their backs, lifting off into the sky, lending the phrase “we’ll bring him up” an aura of salvation. In the end, the three curl up as a makeshift family amidst a world that is still vastly imperfect but full of love.

We are all in the dumps

For diamonds are thumps

The kittens are gone to St. Paul’s!

The baby is bit

The moon’s in a fit

And the houses are built

Without walls Jack and Guy

Went out in the Rye

And they found a little boy

With one black eye

Come says Jack let’s knock

Him on the head

No says Guy

Let’s buy him some bread

You buy one loaf

And I’ll buy two

And we’ll bring him up

As other folk do

In many ways, this is Sendak’s most important and most personal book. In fact, Sendak would resurrect the characters of Jack and Guy two decades later in his breathtaking final book, a posthumously published love letter to the world and to his partner of fifty years, Eugene Glynn. Jack and Guy, according to playwright Tony Kushner, a dear friend of Sendak’s, represented the two most important people in the beloved illustrator’s life — Jack was his real-life brother Jack, whose death devastated Sendak, and Guy was Eugene, the love of Sendak’s life, who survived him after half a century of what would have been given the legal dignity of a marriage had Sendak lived to see the dawn of marriage equality. (Sendak died thirteen months before the defeat of DOMA.)

All throughout, the book emanates Sendak’s greatest lifelong influence — like the verses and drawings of William Blake, Sendak’s visual poetry in We Are All in the Dumps with Jack and Guy is deeply concerned with the human spirit and, especially, with the plight of children. See more of it here.

AMY ASKS A QUESTION: GRANDMA, WHAT’S A LESBIAN?

Children are our greatest antidote to the narrowing of personality and their pure, earnest curiosity about the unfamiliar only turns into negative judgment or aversion when these responses are modeled by fearful, bigoted, and narrow-minded adults. But, conversely, when children are aided in understanding the unfamiliar rather than judging or fearing it, the seed of benevolence and compassion is planted. That’s the heartening premise behind the 1996 gem Amy Asks a Question: Grandma, What’s a Lesbian? (public library), written by Jeanne Arnold and illustrated by Barbara Lindquist — two grandmothers themselves, who explain in the afterword that twenty years earlier they had fallen in love and stepped out of their “heterosexual privilege.” The book is loosely based on their own lives and dedicated to their six children and eleven grandchildren — doubly delightful today, as we face the disappearance of grandparents from literature.

It tells the story of little Amy, who comes home one day and tells her parents that some boys at school had teased her and the other little girls for hugging each other, calling them “lesbians.” Amy isn’t sure what that means or why it’s an insult. Her parents decide that the question is best addressed by Amy’s grandmother, Bonnie, who has been living with her partner Grandma Jo for more than twenty years.

One Mother’s Day, Amy goes to visit her two grandmas. As she sits in their big armchair pretending to be reading one of their countless books, she overhears them talking about “gay pride” and wonders what that means. She knows what “gay” means — her favorite uncle, who taught her to sign for the deaf, was gay and died of AIDS — but she doesn’t get the pride thing.

Pride? I feel proud of myself when I get my good reports at my school, when I learned to play the flute, and when I help my mom and dad watch out for my brother and sister. Grandma Bonnie is an artist. Her paintings fill the walls of their home. She is an author, a musician, a computer expert and a woman who owns her own business. And she’s proud of all that. She’s proud of all her four children and eight grandchildren. Why does she want to go to a gay pride parade to feel proud?

Amy knows fragments of her two grandmas’ life-stories — how they met at the hospital where they both worked and where Grandma Jo still works part-time; how Bonnie got fired when management found out that she had gotten divorced and was now living with Jo; how they opened a women’s bookstore to make ends meet while contributing to the community; how they had a “handfasting ceremony,” which is “kind of like a wedding ceremony,” after twenty years of living together.

So on her next visit to her two grandmas’ house, with her mother’s encouragement, Amy poses the big question: “Grandma, what’s a lesbian?”

“Well,” said Grandma Bonnie. “We’ve been waiting for a long time for that question to come from one of our grandchildren.” Then she took a deep breath and said, “Amy, we are lesbians, Jo and I, and we’re called “lesbians” because we love each other. Lesbians are women who prefer to be with women as friends or who choose women as their lovers and/or partners. Lesbians love women rather than or more than they could love men as lovers or as husbands.

But Grandma Jo interrupts to offer an essential disclaimer that speaks to Amy’s experience with the teasing boys at schools:

But each woman needs to think of herself as a lesbian before anyone else can pin that label on her. You are a lesbian only if you consider yourself one!

Grandma Bonnie adds that they’ve loved each other for twenty years and wistfulness creeps into her words as we’re reminded once again, from the privilege of history’s hindsight, just how much we owe to Edith Windsor:

We would get legally married, if we could.

They go on to recount how in the early years of their love, an era when LGBT couples were truly invisible, they didn’t know any other lesbians at all and felt completely cut off from a sense of community. They tell Amy about the various semi-secret identity signals used to dispel that illusion of hegemony-enforced invisibility:

Lesbians are everywhere — in big cities, small towns and in the country, but they have been almost invisible unless they wear a pink triable pin or a rainbow flag patch on their clothes or have a lavender bumper sticker on the cars saying, “Meet you in Michigan in August.”

The book was published by Mother Courage Press, an imprint Arnold and Lindquist founded to give voice to women’s words. Arnold’s afterword is a heartening testament to how far we’ve come in the two decades since as well as a poignant reminder of how little some things have changed and how much further we have yet to go:

I want to celebrate lesbian values, courage and respectability, our uniqueness and our struggles in the pursuit of happiness. Many lesbians’ lives go uncelebrated, even unacknowledged. A profound silence casts a shadow over them and their families, friends and co-workers. Many of us have been or are so invisible, it’s as if we are in a secret sorority; it seems like a miracle when we find each other. This silence denies our worth. This silence weakens our lives and our families already vulnerable to society’s pressures. Those women-loving women who reveal who they are risk themselves each day. The challenge they have accepted is sustained by the courage that it takes to be themselves. […] Energy is wasted by those living in secrecy and silence. It is also wasted by those divided in conflict… The conflict consumes the power that could be better spent strengthening the individual, the family and society in a world without oppression and heterosexism — with people living in freedom and thriving in love.

KING AND KING

From Dutch writer and illustrator duo Linda de Haan and Stern Nijland comes the irreverent, imaginative, absolutely wonderful 2002 treasure King and King (public library) — a fairy tale with a refreshing twist.

This magnificent book — which has been consistently challenged and even brought to court by small-minded bigots and yet remains widely beloved the world over and has been adapted for the theater stage in Vienna and Mexico City — tells the story of a young prince whose grouchy queen-mother, ready for retirement after many long years of ruling the kingdom, keeps pressuring him to get married.

In a rather common defense strategy against maternal nagging, the prince reluctantly agrees to the queen’s unrelenting demand, but not without noting that he “never much cared for princesses.”

The queen brings all of her royal determination to the task and calls the princesses of “every castle, alcazar, and palazzo near and far.” One by one the eligible bachelorettes present themselves to the prince, but none is right — not the “funny little princess from Greenland,” who ends up besotting the prince’s page, nor the pageant queen from Texas who fails to impress the royal family with her juggle act, not even the tall, dark, and elegant beauty from Mumbai, who storms out after the prince remarks that her long arms would be well suited for waving to the people.

Just as the prince and the queen begin to sink into defeat and disappointment, the page announces that there is one more princess, escorted by her brother, Prince Lee.

And as the fairy-tale trope goes, the last resort is the one where the key to happily-ever-after is hidden — except not in the precise way the queen had intended.

As soon as the two princes lay eyes on each other, they fall madly in love as the queen grumbles silently and the princess yawns.

But their wedding is so magical that even the queen can’t help shedding a tear or two. For a delightful touch, Nijland places a groom-and-groom duo atop the wedding cake as the two princes stare lovingly into each other’s eyes under a “CONGRATS” banner.

At last, the queen is free to retire and the two princes take charge of the kingdom, known from that day on as King and King. “And everyone lives happily ever after,” of course.

King and King was followed by King and King and Family, the equally delightful story of the duo’s honeymoon, on which they go to the jungle and see all kinds of animals having babies, so they decide to adopt a child and venture into parenthood themselves.

AND TANGO MAKES THREE

And Tango Makes Three (public library) by Justin Richardson and Peter Parnell, with charming illustrations by Henry Cole, tells the heartening true story of Roy and Silo — two male chinstrap penguins at the Central Park Zoo. Roy and Silo fell in love in 1998 and started a family, raising little Tango — the zoo’s first and only baby-girl with two daddies.

Published in 2005, nearly a decade before marriage equality, the book is a sweet celebration of modern families through the most indisputable and inclusive assurance — nature itself.

But nothing happened. Then, Mr. Gramzay got an idea:

But the true story has a bittersweet ending — in 2005, just after And Tango Makes Three was published, Roy and Silo parted ways and Silo coupled with a female penguin. Meanwhile, Tango formed a same-sex relationship with another female penguin named Tanuzi. Tango and Tanuzi have remained together for every mating cycle since.

DADDY’S ROOMMATE

Daddy’s Roommate (public library) is the inaugural title by Alyson Wonderland, a children’s-book imprint aimed at offering comfort and camaraderie to the children of LGBT parents.

Written and illustrated by Michael Willhoite in 1990, it tells the story of a little boy whose dad begins living with a man named Frank shortly after he and the boy’s mom divorce. It’s a simple, quietly assuring tale of how the child arrives at loving acceptance of his newly reformulated family as he bears witness to the ordinary day-to-day lives of Daddy and Frank.

In the afterword to the tenth anniversary edition, Willhoite looks back on the “wrath of the religious right,” which descended upon the book when it was first published and how it accomplished exactly the opposite of what those bigoted censors desired — it catapulted the book into national prominence as libraries all over the country “fought like tigers on the book’s behalf.” Willhoite writes:

Daddy’s Roommate has been the target of censorship, burning, theft, defacement, and a well-orchestrated campaign to remove it from libraries. The book is still, triumphantly, what I first intended: a mirror in which children of gay parents can see themselves. Yet it has also been used as a tool to educate children in more traditional families about gay families in their midst. I am very proud.

HEATHER HAS TWO MOMMIES

In the 1980s, writer Lesléa Newman began noticing that same-sex couples were having kids like everybody else, but had no children’s books to read to them portraying nontraditional family units. At that point, women had been “marrying” one another for ages, but true marriage equality in the eyes of the law and the general public was still two decades away, as were children’s books offering alternate narratives on what makes a family. So Newman enacted the idea that the best way to complain is to make things and penned Heather Has Two Mommies (public library) — a sweet, straightforward picture-book illustrated by Diana Souza, telling the story of a warm and accepting playground discussion of little Heather’s life with Mama Kate, a doctor, and Mama Jane, a carpenter. Today, it is notable primarily for its pioneering status as the world’s first children’s book about a two-mom family.

Heather’s favorite number is two. She has two arms, two legs, two eyes, two ears, two hands, and two feet. She also has two pets: a ginger-colored cat named Gingersnap and a big black dog named Midnight. Heather also has two mommies: Mama Jane and Mama Kate.

The book, which predated even Maurice Sendak’s controversial children’s story grazing the subject, was unflinchingly pioneering — with the proper social outrage to attest to this status. Not only did it rank number 11 on the American Library Association’s chart of America’s most frequently challenged books in the 1990s, but its impact continued for decades — comedian Bill Hicks, an eloquent champion of free speech, paid homage to it in his final act on Letterman in October of 1993 and it was even parodied in a 2006 episode of The Simpsons titled “Bart Has Two Mommies.”

Despite that, or perhaps precisely because of it, the book lives on as a bold embodiment of Bertrand Russell’s famous proclamation: “Do not fear to be eccentric in opinion, for every opinion now accepted was once eccentric.”

Twenty years later, Newman followed up with the board books Mommy, Mama, and Me and Daddy, Papa, and Me, affectionately illustrated by artist Carol Thompson.

Complement Heather Has Two Mommies with Andrew Solomon’s remarkable Far From the Tree: Parents, Children and the Search for Identity, a moving meditation on how love both changes us and makes us more ourselves, and the impossibly charming And Tango Makes Three, an allegorical marriage equality primer telling the true story of Central Park Zoo’s gay penguin family.

In the decades since, Newman has authored a number of other LGBT-themed children’s books, including Gloria Goes to Gay Pride. A modernized edition of Heather Has Two Mommies, featuring new illustrations by artist Laura Cornell, is being released in March 2015.

MORRIS MICKLEWHITE AND THE TANGERINE DRESS

Of all the imprisoning polarities and stereotypes in our culture, none is more pervasive than the imprisoning gender expectations we instill in kids from an early age. Even young Mark Twain took issue with them in his irreverent 1865 gem Advice to Little Girls , and a New Yorker cartoonist satirized them brilliantly a century later. Today, the situation is improving only slowly, only modestly, thanks to the occasional children’s book encouraging young girls to transcend our gendered vocational stereotypes. But what about little boys who don’t relate to society’s prescription for how they should inhabit their own identity and don’t understand why they aren’t allowed to enjoy what little girls enjoy? As Erika Trafton wrote in her moving meditation on gender identity, “This culture wants little boys to dream only of baseball, trucks, and trains. This culture has no room for little boys who want to be gorgeous.” And yet Andrew Solomon put it best: “Loving our own children is an exercise for the imagination.”

That exercise is what writer and anti-bullying champion Christine Baldacchino and illustrator Isabelle Malenfant explore with great warmth and tenderness in Morris Micklewhite and the Tangerine Dress (public library) — the story of a sweet but misunderstood little boy derided and ostracized by his classmates because he loves wearing the tangerine dress in his classroom’s dress-up center.

Imaginative and wildly creative, little Morris likes to paint and sing and do puzzles while humming to himself. He loves the tangerine dress because its color “reminds him of tigers, the sun and his mother’s hair”; he loves the sound it makes, too: “swish, swish, swish when he walks and crinkle, crinkle, crinkle when he sits down.”

When the boys make fun of him and the girls jeer at the pink nail polish on his fingers, he pretends not to notice them, but his heart aches with anguish.

His classmates even shun him from the spaceship they are building — “Astronauts don’t wear dresses,” they scoff.

One day, Morris is so crestfallen over the ceaseless bullying that he begins to feel physically ill. (Indeed, psychologists are now finding that “social pain” has biological repercussions.) He is sent home, where he dreams up a grand space adventure with his cat Moo.

The next day, Morris takes out his brushes and paints a wild, vibrant picture of his dream, complete with a shiny space helmet for Moo. In the drawing, Morris is wearing his beloved tangerine dress riding atop a big blue elephant.

On Monday, Morris went to school with his painting rolled up in his backpack. When he had the chance, he put on the dress that reminded him of tigers and the sun and his mother’s hair. Morris swish, swish, swished.

The tangerine dress crinkle, crinkle, crinkled.

His shoes click, click, clicked.

Morris felt wonderful.

The boys in his class are so enchanted by the space-world Morris dreamt up — a world into which he welcomes them — that they decide “it didn’t matter if astronauts wore dresses or not” because “the best astronauts were the ones who knew where all the good adventures were hiding.” With a quiet smile, Morris accepts their acceptance.

When snack time was over, Becky demanded the dress.

Morris told her she could have it when he was done with it.

“Boys don’t wear dresses,” Becky snipped.

Morris smiled as he swished, crinkled and clicked back to his spaceship.

“This boy does.”

* * *

Complement with this reading list of stimulating children’s books celebrating science and this grown-up omnibus of history’s most beautiful LGBT love letters, then revisit The Little Red Schoolbook — a wonderfully honest vintage Danish guide to teenage sexuality, brought back to life after decades of being banned.