Simon Rich’s Scary New York

When Simon Rich was growing up and walking around the streets of New York he was always afraid of an

When Simon Rich was growing up and walking around the streets of New York he was always afraid of an air conditioner falling on his head.

“I still walk closer to the curb because I’m sure that’s going to happen,” the 26-year-old novelist SNL writer said over iced coffee last week.

For Mr. Rich, whose writing is often inflected with an impending sense of doom — God makes completely irrational decisions, Dracula poses as the Red Cross — New York has always been a scary place. In his own assessment, living here has instilled an intensely neurotic style in all his writing.

“Just the sheer population makes it a scary place and with a city this packed with people there are sure to be a few murderers on your block,” Mr. Rich deadpanned.

John Mulaney, an SNL writer with whom Mr. Rich writes frequently, said that these jokes are typical of Mr. Rich.

“I think nothing makes him laugh more than freaking out and panicking,” Mr. Mulaney said.

Mr. Rich’s illustrious origins are well documented. His father is Frank Rich, the Times columnist, and his brother Nathaniel is an editor at The Paris Review. His first book of jokes came out mere months after graduating Harvard — he has since published a second humor book — and he’s working on the screenplay for his recently optioned novel Elliot Allagash, which was published in May. News of the film deal provoked an angry rant on Gawker, but Mr. Rich said he has “sympathy and respect” for his haters.

“I think that’s not even the biggest travesty,” he said of his perceived nepotism. “The biggest travesty is that anybody gets to write jokes for a living. It’s a ridiculous profession and I feel like it should probably be against the law for everyone not just the children of successful journalists.”

When Mr. Rich walked into the Brooklyn Heights restaurant where we met him, he could have been mistaken for a student on the way home from school, wearing a loose red polo shirt and carrying a backpack. Later on, three children began to make faces at him through the restaurant’s window. 

“Hey kids!” he said smiling at them, admiring a small black toy carried by one of them. “I feel like toys are cooler now.”

Youth has been a fertile source of material for Mr. Rich. Elliot Allagash is set at a fictional New York private school not unlike Mr. Rich’s alma mater Dalton, and SNL cast member Bill Hader, 32, pointed out that if an SNL sketch ever involves a fairytale, Mr. Rich had a hand in it.

For the record, the school in the book is not Dalton. “I thought it would be more Dalton-y but it’s not,” said one of Mr. Rich’s former teachers.

“I always write out of a sense of fear and doom,” Mr. Rich said. Obviously New York provides him with ample material there, as does being Jewish and reading about God’s smiting in the Torah when he was younger. “The Old Testament God is just a hilarious comedy character,” he said. 


WHENEVER MR. HADER visits Brooklyn Heights Mr. Rich gives him and his wife the “hard pitch” on the neighborhood.

“[He] takes us on a long walk and… knows the all the little interesting anecdotes about each building like, ‘that’s where Norman Mailer wrote whatever book,’ ‘that’s where Truman Capote wrote Breakfast at Tiffany‘s. He lived on the garden level,'” Mr. Hader said.

Mr. Rich does most of his writing in his own Brooklyn Heights apartment, by the window. He and Mr. Hader worked on their horror comedy screenplay for Judd Apatow in that apartment. When Mr. Rich and Mr. Hader write they take breaks at the local deli Lassen & Hennigs where Mr. Rich orders a Knickerbocker — a sandwich with fried chicken, bacon, cheddar and mayo on a buttered roll — which he said he eats about three times a week. SNL head writer Seth Meyers said via email that watching Mr. Rich wait for his sandwich at the Second Avenue Deli on rewrite day is a “true joy.”

Mr. Rich is aware that he draws on his unique angle on New York in his novel.

“It’s certainly not McInerney’s or Bret Easton Ellis’ New York,” he said. “It’s more about the idea of New York.” In this way, he thinks Elliot Allagash‘s New York is like the London of P.G. Wodehouse, or Arthur Conan Doyle.

Simon is “fairly fanatical about the city, its history, its lore,” according to his father, who told us that his sons’ recommendations for New York reading have led him to books he may not have otherwise discovered.

Simon’s brother Nathaniel wrote: “All three of us are obsessed with New York lore, with the city in previous eras, its forgotten and hidden aspects, its purest expressions of urban insanity. But we share other obsessions too: hot sauces, the Mets, Sichuan food.”

Comedy was one of Simon’s personal obsessions. As a kid, he would around 30 Rockefeller Plaza, now his work place, to catch glimpses of the Late Night with Conan O’Brien writers and would pass by the Your Show of Shows writers’ room near Carnegie Hall just to marvel at the “holy moly” — his words — quality of it.

Now, though, Mr. Rich seems content with the “holy moly” of Brooklyn Heights.

“There’s a plaque on a brownstone near here that claims that the curveball was invented in Brooklyn Heights,” Mr. Rich told us. “Like, the pitch. And that alone is reason enough to live in this neighborhood.”

“He was probably burned for being a warlock,” he added, referring to the inventor. “What a terrifying thing to make a ball curve.”

Simon Rich’s Scary New York