When I was a child, growing up in the various parts of India to which my father’s job took us, books were my friends, and I liked them funny. I discovered my grandfather’s P. G. Wodehouse collection at the age of eleven and was at once enchanted by the amiable lunacy of fictional worlds like the Drones Club and Blandings Castle. Lovable and ludicrous, they allowed me to claim an understanding of characters very different from me. I was at that age when laughter comes easily and convoluted story lines feel newly accessible. Plum’s immortal farces were a gift.

But funny isn’t something we’re taught to respect. That could be why, when writers embark on the serious business of crossing cultural boundaries in their work, they don’t often start out with humor. In 2004, Cynthia and Greg Leitich Smith spoke at the Reading the World conference about the dearth of funny books with cultural resonance. Why, they asked, are multicultural books so very serious?

It was a valid question then. What’s surprising is the degree to which it remains valid today, especially in books for middle-grade readers. Books set in foreign countries are still largely about oppression, while those in hyphenated-American communities are about the challenges of finding oneself and becoming American. While many have humorous moments, they are not, by and large, funny books.

It seems especially necessary that children’s books, in the balance, convey more than a one-dimensional image of “the other,” yet the identity tale of oppressed people continues to dominate those books dubbed “multicultural.” Perhaps the problem is that the very notion of a culturally grounded story is perceived as worthy and important, not concepts we associate with laughter. But the truth is that you can’t see people as fully human if all you can feel for them is pity. Funny books with cultural contexts are capable of subverting and questioning issues of identity and belonging. By upsetting worthy apple carts, they offer new and necessary views of characters with cultural connections beyond the mainstream.

The pioneer in mixing humor with matters of race, culture, and, yes, oppression is undoubtedly Christopher Paul Curtis. The Watsons Go to Birmingham—1963 was published in 1995. The scene in which Byron’s lips get stuck to the family car’s side-view mirror is the one most readers call to mind, but there are others, many of them much more pointed than that one, as when the boys are faced with the prospect of going to the bathroom in the woods. Byron says, sardonically, “Snakes? I ain’t scared of no damn snake, it’s the people I’m worried about.” He means white people, of course, on the family’s journey south. The humor slams the reader with the grimness of the circumstances, even while it gives the characters a means of coping.

Humor in The Watsons is a mechanism Curtis uses to lead readers to an understanding of the insidiousness of racism and discrimination. It allows us to align clearly with one group of people and against another, in a deliberate stance that counters the prejudices of the period. If you’re with Kenny and his family, you can’t condone the racism they have to endure. Inequity, discrimination, and injustice give thematic impetus to the characters’ journeys. Because we can laugh, we can bear to navigate those obstacles along with them.

Since 1995, other writers of multicultural books have ventured into humorous terrain. In Julia Alvarez’s How Tía Lola Came to Visit Stay, the unorthodox use of a strikeout in the title places a tongue-in-cheek tonal stamp on the work before the reader has turned a single page. It’s plain that this relative is about to change young Miguel’s life forever. He can’t hold out against this woman who is practically a force of nature, and neither can the reader. Her character, larger than life and twice as real, creates a playfulness that runs through the book and its sequels.

One way to cross cultural borders is by normalizing customs and preferences that might typically be seen as un-American. Lenore Look does this in her chapter books with Chinese American protagonists. In Ruby Lu, Brave and True, for example, foods like “jook” are casually named in passing. Don’t know what that is? Well, all right, there’s a glossary, but does it really matter? After all, when I read Enid Blyton in my youth I had no idea what scones were. It didn’t stop me for a minute.

Ruby’s Chinese school is cleverly normalized by the elegant teacher, by the funny coincidence of a namesake friend, and by Mom’s memories of English school in China. A bilingual dog responds to commands in Cantonese and English—a subtle suggestion that in this world, both languages are equally privileged. Normalizing the unfamiliar allows the reader to laugh with, rather than at, the character in such a story. It also implies that you don’t need to understand everything about a person in order to share a smile. By placing cultural markers in this way, the writer draws borders between cultures, and then makes them permeable, thereby giving the reader permission to laugh.

Look’s Alvin Ho books feature an endearing boy character with a family and community whose imperatives are often at odds with his own fears. The first two books, Alvin Ho: Allergic to Girls, School, and Other Scary Things and Alvin Ho: Allergic to Camping, Hiking, and Other Natural Disasters, and the fourth, Alvin Ho: Allergic to Dead Bodies, Funerals, and Other Fatal Circumstances, are laugh-out-loud funny. They adroitly traverse the emotional spaces of Alvin’s Concord, Massachusetts, neighborhood and his Chinese American family. A less felicitous choice in the third title, Alvin Ho: Allergic to Birthday Parties, Science Projects, and Other Man-Made Catastrophes, is a plot line related to “playing settlers and Indians” at a friend’s birthday party. Perhaps unintentionally, it nonetheless objectifies American Indians, and normalizes a controversial playground remnant from the colonial past. To me, it seemed a perplexing and discomfiting element. Sometimes those cultural border-crossing zones contain landmines. Sometimes a joke can backfire. Maybe it’s just that as a writer from an underrepresented group myself, I feel a need to be particularly mindful when I’m engaged in the representation of others.

In Daniel Pinkwater’s The Neddiad: How Neddie Took the Train, Went to Hollywood, and Saved Civilization, the narrative voice leads readers into a richly funny rendition of 1940s America. The book stars Neddie, son of the Wentworthstein shoelace king, along with a sizable cast of eccentric characters. Nor is race ignored as a social factor of the time—a racist comment made at the Brown-Sparrow Military Academy hits home because of its offhandedness. Neddie doesn’t get it, but the reader will.

The Neddiad and its sequels, The Yggyssy and Adventures of a Cat-Whiskered Girl, are madcap escapades with space aliens, baffling allies, and true-blue villains. Houses appear and vanish at whim, the Catskills are peopled with giants, reality itself sometimes seems a mirage, and the jokes range from subtle to slapstick and everything in between. Time itself may be the cultural border crossed in these books. They take the reader into a past with many racial, cultural, and even religious strands, from all of which Pinkwater weaves a genuinely American humorous fantasy.

A comparable book with clear cultural context is Salman Rushdie’s Haroun and the Sea of Stories, where comic book and cartoon conventions meet the movies of Satyajit Ray. The book is a phantasmagorical journey driven by the ill will of a villain who represents the silencing of all stories.

The sequel, Luka and the Fire of Life, draws its inspiration from sources as diverse as Beowulf and Super Mario. While equally filled with dramatic moments, it lacks the ingenuity, the freshness, and the heart of Haroun. Both books, however, are packed with layers of humor accessible to all, along with bilingual jokes that are special treats for cultural insiders.

It’s hard to juggle insiders’ jokes while crossing cultural borders, but they can be used simultaneously as a nod to readers in the know and an invitation to others. In Janet Wong’s verse novel Minn and Jake, Jake’s racial background is never mentioned. In the sequel, Minn and Jake’s Almost Terrible Summer, we learn that he has a Korean grandmother. That makes him one-quarter Korean, or as he says, “Quarpa.” By punning on the insider’s term hapa, the author invites not only Minn to share in the joke but the reader as well.

Humorous outsider narratives are even rarer than funny books written from within the cultures concerned. It’s easy to see why. When you’re treading on unfamiliar ground, humor can seem to add an unnecessary banana peel. The outsider risks being tripped up by nuance and implication, regional specificity and the dangers of caricature. Candace Fleming takes all these risks and more in Lowji Discovers America, her story of a boy from India whose family is Parsi, belonging to the Zoroastrian faith. Lowji’s spunky character and his occasional precocity go far in establishing his appeal. A best friend left behind in India is counterpoint to new friends in America without for a minute implying a hierarchical comparison between the two. Of course, humor can also sometimes have a long fuse, tapping the deep and personal sources that Eudora Welty said give rise to all story. As a result, it’s possible that to a Parsi reader, some element or other might ring false. Sometimes writing funny books can call for bravery in a writer.

An improbable combination (best friends in suburban Maryland and an eccentric Bollywood movie star) served as my entry into the subversive world of humor. My middle-grade novel The Grand Plan to Fix Everything employs cultural fusion to define the relationship between best friends of whom one is Indian-American and the other is not. Eleven-year-old Dini is devastated because her family’s impending move to India means that she and her best friend Maddie will have to miss Bollywood dance camp—in Maryland.

There is no question in my mind that whatever loopiness I’ve succeeded in bringing to the page I owe to those Wodehouse novels I read years ago. They were not written for children, but I read them with my eleven-year-old hunger to understand the world. Humor can help a reader do just that. It must be handled with care, so the reader is laughing with the characters and situations, as in the work of Christopher Paul Curtis, and not at them.

In generous hands, humor can appear to fix the things that need fixing in the world. And then it can turn around and wink at you, the reader, as if you’re complicit in the manufacture of the fiction. Children in the middle grades are eccentric, idiosyncratic, and poised on the brink of reinventing both themselves and their world. The middle-grade reader is a perfect audience for the writer seeking to bridge gaps, make connections, or cross borders of culture, race, place, and language—with laughter leading the way.

From the May/June 2012 issue of The Horn Book Magazine.