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Scared Silly

Nothing inspires first-time author and Harvard Lampoon alum Simon Rich more than his own insecurities.

(Photo by David Bartolomi)

Twenty-two-year-old Simon Rich may have graduated from Harvard in January, but he freely admits he has yet to outgrow the ordeal of adolescence. Back in Hebrew school, for instance, he was terrified of a wisecracking classmate named Zach, an aspiring juvenile delinquent who wore a leather jacket. For Rich, the memory of Zach still represents a certain kind of worldliness, a studied ambivalence, that he’ll never attain. And that kind of insecurity, he thinks, is just about the funniest thing in the world.

The skinny writer’s nebbishy anxieties saturate his debut book of humor pieces, Ant Farm and Other Desperate Situations, which comes out this week. His brand of wit bypasses the heavy sarcasms and ironies of the moment in favor of a sweeter, sillier, more absurdist shade of comedy, one that capitalizes on his own vulnerabilities. In one typically bite-sized entry called “A Conversation at the Grown-Ups’ Table as Imagined at the Kids’ Table,” Rich has Grandma wondering if anyone heard the news about “the politics.” Mom mentions that there was “a big sex” in the PG-13 movie she just saw. And “there are actual monsters in the world,” says Dad, laughing, “but when my kids ask I pretend like there aren’t.”

Rich’s real-life dad is Frank Rich, who writes about political and show-business monsters for The New York Times. “We do very different kinds of writing,” the younger Rich offers cheerfully. “My dad writes about the fate of the free world, and I write about dogs, video games, and bears.” He jokes that none of his Harvard friends ever bothered to engage him in debates over his father’s opinions. “They pretty much know how little I know about the world,” says the unfailingly genial Rich, his wavy brown hair whisked past his earlobes, his whippet-thin frame curled over a Dunkin’ Donuts cup in Harvard’s Science Center.

Rich, who opted out of the honors program while earning his degree in English and American literature and language, filled his course load with curious electives that often brought him into this building: “Medieval medicine, a history of treating the insane, classes about angels, a bunch of classes about monkeys. I took one called the behavioral biology of women. It was a disaster.”

Not that he didn’t find it useful. As a former president of Harvard’s prestigious century-plus humor publication, the Lampoon – a membership he swears he aspired to years before he was old enough to consider college – Rich is forever probing the comic underbelly of everything. “It’s a great place to learn how to write,” he says of the satirists’ club that has produced looming cultural figures, from William Randolph Hearst to Conan O’Brien, not to mention large chunks of the writing staffs on today’s cleverest TV shows. “You don’t have to worry about pleasing crowds, because there are none.” From his first staff meeting at the Lampoon, he knew he’d found a home. “People are so terrified of making eye contact, and everyone had worse acne than I did. I was worried that everyone would be like that Hebrew school kid in the leather jacket, but they’re very introverted, sad, bitter, funny, talented people. I love them.”

Picking up where his work at the Lampoon left off, Ant Farm largely consists of giddy what-if scenarios: What if an endangered panda blew all his mating opportunities with awkward pickup lines? What if a former boyfriend returned to redeem the “love coupons” his ex gave him years ago? What if the Swiss Army used its namesake knives as actual weapons? Fear, Rich says, is his underlying theme, be it a fear of math problems, social ineptitude or, yes, the fate of the free world.

Rich’s style, says Scott Dikkers, editor-in-chief of the satirical newspaper The Onion, is “a mix of absurdist humor and trenchant satire, which feels really new. It’s like [Steve Martin’s 1979 book] Cruel Shoes, with something to say.” Dikkers, who read an early draft of Rich’s book on the recommendation of their mutual literary agent, says the author is at the forefront of a shift among comedy writers who were reared on a steady diet of The Onion and sketch groups like The Kids in the Hall but who are somehow gentler.

Rich himself is quick to admit a long list of influences, including The Simpsons, Roald Dahl, Seinfeld, Woody Allen’s book Side Effects, MTV’s short-lived sketch show The State, and Mad magazine. He discovered a lot of his reading material on the shelves of his older brother, Nathaniel, who published his own first book, a history of San Francisco in film noir, in 2005. It may come as no surprise by now that self-effacing Rich considers his brother, four years his senior, to be impossibly sophisticated.

After finishing his final exams, Rich moved back into the midtown Manhattan apartment where he grew up, still occupied by his mother, Gail Winston, an executive editor at HarperCollins now divorced from Simon’s dad. “I’m planning to stay there for a very long time, as long as it’s socially acceptable,” he says. “My mom doesn’t know this yet. Just between you, me, and Boston, I have no plans to leave.”

He does, however, have the back end of his two-book deal with Random House to fulfill, so he’ll be working on more humor pieces for the immediate future. And he’s already been “wined and dined by Hollywood,” as Dikkers puts it. Will he eventually try to follow other Harvard alumni onto the writing staffs at The Colbert Report, The Office, or Conan? “I don’t think TV writing is easy,” Rich says. “For the moment, I’m sticking with this format. I really dig it.”

While his publishers are betting he has identified a certain style of humor that will ring true for his generation, the author is amused by the idea that he might be considered an authority. “I have no idea how college students think.”

James Sullivan is a freelance writer in Amesbury. E-mail him at