A Toddler Detective, Pirate Parents and Other Witty Treats in Simon Rich’s ‘New Teeth’

“Listen to this,” I said to the person I live with, waving Simon Rich’s latest book of short stories, “New Teeth,” in the air. It was bedtime. He put down his own book.

“The detective woke up just after dawn,” I read aloud. “It was a typical morning. His knees were scraped and bruised, his clothes were damp and soiled, and his teeth felt like someone had socked him in the jaw. He reached for the bottle he kept under his pillow and took a sloppy swig. The taste was foul, but it did the trick.”

Alert readers will recognize the cadence, vocabulary and world-weary tone of Raymond Chandler in “The Big Sleep.” But this detective is even more clueless than Philip Marlowe: He’s a toddler looking for a lost stuffed unicorn who can’t even figure out how the client, his own baby sister, got into the house.

“Her past was murky,” Rich writes. “The detective had heard that she came from the hospital. But there was also a rumor she’d once lived inside Mommy’s tummy. It didn’t add up. Still, a job was a job.”

A triumph of sustained humor that works equally well as a parody of hard-boiled noir detective fiction and as a moving account of siblings banding together against a world that makes no sense, “The Big Nap” is the best thing in an uneven but mostly delightful book by the extravagantly talented Rich. Really, I wish I could just keep quoting from it.

“Look, you’re just a kid, so I’ll spell it out for you,” the toddler says to the infant, describing the vast conspiracy that surrounds them like a spider’s web. “Mama’s the big boss around here. She pulls all the strings. The doctor, the dentist, the Gymboree instructor — they’re all on the take. Everybody answers to her.”

By this point, I was reading every other sentence aloud, while exhorting my companion to read the book himself. This would seem to be a contradiction, but that is what this sort of writing does to you.

Rich, a screenwriter, novelist and former writer for “Saturday Night Live,” among other things, is the author of two novels and five previous volumes of short stories. He has an antic imagination and a delicious wit. His skill at shifting gears midsentence, flinging the reader from absurdity to reality and back, conjures the sublime early writing of Woody Allen.

Many of the stories in “New Teeth” are told from the perspective of characters who do not fully comprehend their own circumstances. (Welcome to the club.) In “Chip,” an irony-free robot employed by a soulless company narrates what he sees, to the consternation of the firm’s frat-boy executives.

“Paula originated the idea,” the robot declares, after the executives ignore a female employee’s marketing suggestion and then loudly repeat her idea as if they had thought of it themselves. “I observed that the men were still confused,” the robot tells us, “so I projected a hologram clip of the meeting from my chest, which plainly showed the order of events.”

Banished forthwith to an obscure cubicle in a far corner of the office where Paula has been toiling alone for 16 years, Chip is at a loss until he helps Paula carry out a cunning plan to turn the tables. The result is both surprising and satisfying.

In another story, a laser disc player moldering on the shelf suddenly wakes up from a decades-long siesta to find that its not-young-anymore owner, John, no longer appreciates its cutting-edge ability to play “not one, but three different films: ‘Backdraft,’ ‘Arachnophobia’ and ‘Right Now: The Music Video,’ by Van Halen.” Unexpectedly switched on again by John, the machine is startled to hear laughter.

“They’re watching you ironically,” the sneering DVD player tells the laser disc player. “They’re watching you to laugh at how you suck.”

“Learning the Ropes” begins when a pirate named Black Bones the Wicked, who “would sooner cut a hundred throats than heed one order from a living man,” rhapsodizes about his carefree existence of carousing, murdering and pillaging with his first mate, Rotten Pete the Scoundrel.

This lifestyle is upended by the unexpected arrival of a tiny girl stowaway, a perfect new partner in crime, thinks Black Bones, after he decides not to toss her overboard. “I was going to be raising the girl in a cool way so that she be ending up cool,” he says. “I was going to teach her to reject conformity and rebel against society and also to listen to cool bands.”

But Rotten Pete has a stricter parenting philosophy and, Black Bones believes, a passive-aggressive tendency to sulk instead of using his words. “I thought about letting it go, because I knew if I be saying something, it would be leading to a fight, and I was just not in the mood,” Black Bones says. “But after some prodding, he threw up his hook hand and said, ‘Arr, I am just tired of always having to be the bad guy with her.’”

I could read all day about a pair of pirates dragged unwittingly into adulthood. The problem with books of short stories, though, is how they knock you around. It’s as if, floating on a cloud of bliss as you waft out of a new lover’s apartment, you have to switch gears and spend the next night with a new, possibly less exciting person.

It’s hard to gin up the same degree of energy and commitment, especially when the new person (in the case of “New Teeth”) is a too-long story called “Revolution,” about a prince’s struggles to understand why the peasants in his kingdom are so aggrieved. I had similarly lukewarm feelings toward “Clobbo,” about a superhero past his prime, and “Screwball,” an intriguingly conceived story that makes Babe Ruth sound unnecessarily oblivious.

But those really are quibbles, and the benefit of a collection is that you get to focus on the stories you like best. Rich’s humor is enhanced by his generous, hopeful heart. I love how in “Raised by Wolves,” for instance, a 35-year-old Verizon employee named Lauren learns to forgive her parents (literal wolves) for what they did to her during her childhood: “The barking, the growling, the total lack of structure and support.”

Fortified by Klonopin and pinot grigio at Thanksgiving, Lauren sees her aging, now-chastened parents playing happily with her own daughter, Haley, and feels a surge of gratitude for “how they’d fed her, sheltered her and defended her from hawks,” Rich writes. “In some ways, her parents’ flaws had even contributed to her success. (She knew, for example, that her essay about them was a major factor in her getting into Brown.)”

Analyzing why it’s so pleasurable to read Simon Rich is about as helpful as analyzing why it’s so fun to spend the night with an unexpectedly excellent blind date. It’s better to do it than to talk about it. I’ll stop now.