What do Cinderella, Psalm 139, King Lear, The Divine Praises, Lorica of St. Patrick, and The Ladder of Divine Ascent have in common? What would a crossover between Kenneth Grahame’s The Wind in the Willows and Donald Barthelme’s Some of Us Had Been Threatening Our Friend Colby look like? What do you get when you mix a Scottish ballad with one of Grimm’s fairy tales? Mallory Ortberg’s wickedly clever collection of stories, The Merry Spinster, draws from fairy tales, literature, and religious texts, and the result is nothing short of magical.

“There’s a rich history of [retelling a well known story]…and that’s something I’ve always done,” says Ortberg. The stories in this collection, which include versions of Beauty and the Beast, The Little Mermaid, and Frog and Toad Are Friends, often poke and prod at lessons that only seem clear-cut, exploring what G.K Chesterton called “the morality of fairy land.”

“[It’s] this idea that you could go to a world where there are incredibly specific rules, and if you break them there are incredibly specific consequences, and they are not necessarily tied to either morality or intuition,” Ortberg says. “When you start with that as your premise, you can put characters in situations that are both baffling and familiar.”

True to their source material, Ortberg’s stories often take those consequences to dire ends. “Cast Your Bread Upon the Waters,” which blends the Orkney folktale “Johnny Croy and His Mermaid Bride” and Thomas Aquinas’ Summa Theologica, delves into the cultural combinations and clashes that occurred during the Christianization of the British Isles. In it, a young man falls in love with a mermaid. The young man’s father, who disapproves of the union, takes matters into his own hands, with horrific, bloody results.

The constant runner in this tale, however, is the father’s absolute surety that what he’s doing is right and necessary. Ortberg had a clear sense of how the character of the father might live both in the world of paganism and the world of Christianity, and how those structures might inform his violent ideas of justice and retribution. “How do you justify a monstrous decision that you’ve decided you have to make?” says Ortberg. “How do you explain it to yourself? And how do you justify it?”

Other stories reflect on abusive relationship dynamics that present as love or friendship, and what it means to suffer or be punished. Ortberg, who recently came out as trans, uses gender and the fluidity of pronouns playfully; Ortberg’s traditionally gendered terms and traits are especially provoking when drawing from source material with notoriously rigid ideas about who women and men are, and what functions they serve in a society or a story. The tales are often impressively frightening, too; Ortberg’s twist on The Velveteen Rabbit recalls the best of Shirley Jackson, with a sinister toy bunny intent on becoming Real, no matter the cost.

Even so, fans of Ortberg’s cult-favorite website, The Toast, famous for sharply written comic essays with titles like “This Guy on an Old Harry Potter Forum Says Dumbledore Is a Time-Traveling Ron Weasley and I Want to Hear Him Out,” have no need to fear that Ortberg has abandoned those humorous roots. “There are moments when something awful and violent and painful happens and you find something funny in it…not to make light of it…but life often looks like that,” says Ortberg. “That was important. I did not want to write a book that didn’t feel like it was funny.”

If those seem like a lot of plates to spin in one collection, you’re right. Ortberg’s first book, Texts from Jane Eyre: And Other Conversations with Your Favorite Literary Characters, sold well. “I knew if that happens you can usually sell your second book, even if you want to take a bit of a risk,” says Ortberg. “And I felt like what I want to do is something different, such that even if that doesn’t do well at least I spent the goodwill of the first book doing something that was different.”

Chelsea Ennen is an editorial assistant at Kirkus Reviews.