Rich, a cheerful father of two who got his start on television writing for “Saturday Night Live,” delights in riding the line between comedy and horror. “I love writing stories that start in a place of abject nihilism and end up being redemptive in some way,” he said.
If Rich is not the finest comic short story writer alive, he is likely the one most beloved by comedians. Jon Stewart and Patton Oswalt blurbed him. John Mulaney enlists his help every time he hosts “Saturday Night Live.” When I asked Conan O’Brien about Rich, his eyes lit up: “He’s my cup of tea.”
The reason, I suspect, is that like most comics, Rich works as if he’s nervous about losing the attention of his audience. His stories are brief, using language that never shows off. Susan Morrison, his longtime editor at The New Yorker, said his spare style is what first stood out. “One of the unique things about him is that young people who write funny stories often suffer from ornate writing — lots of five-dollar words,” she said. “Simon’s writing is so tight. It’s like if Raymond Carver or Hemingway wrote funny stories.”
Rich, the son of the book editor Gail Winston and Frank Rich, who took him to plays as a boy when he was reviewing them for The Times, has had a wildly precocious career (one of the youngest writers in “S.N.L.” history) that followed attending a few of the most elite educational institutions (Dalton, Harvard). He is quick to skewer his advantages (one collection is called “Spoiled Brats”), and in the essay “The Book of Simon,” which includes a character with his name, he uses his privilege as a case against the Divine.
“If God existed,” he writes, “then surely by now he would have gotten some horrible comeuppance.”
Rich knew he wanted to be a writer since at least early elementary school and obsessed over Roald Dahl and Mad magazine, but it took him a while to figure out what kind. Despite his love for horror fiction along with what he calls “blow-your-brains-out psychological realism” (Richard Yates, the author of “Revolutionary Road,” is a favorite), he said he tried and failed at both. Like many young funny writers, he wrote his Philip Roth rip-off but that didn’t cut it.
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