Simon Rich: Is he the Woody Allen for Millennials?

Simon Rich was born in 1984 in New York City. The son of New York Times columnist Frank Rich, he attended Dalton High School before completing his impeccably preppy education at Harvard, where – in hindsight, almost inevitably – he was president of the Harvard Lampoon. Before graduating in 2007 he signed a two book contract with Random House, placing him in the wunderkind league of Bret Easton Ellis and Michael Chabon. Ant Farm and Other Desperate Situations was published in April 2007, with Free Range Chickens following in 2008. Ant Farm was nominated for the Thurber Prize for American Humour. A representative slice of the material in these books is Rich taking the original Marathon runner, Pheidippides, to the NYC marathon.

“ME: Hey, look at that old guy with the beard! Pretty inspiring, huh? Still shuffling around after all these years.

PHEIDIPPIDES: We must rescue that man. We must save his life.

ME: Oh, he knows what he’s doing. He probably runs this thing every year.


PHEIDIPPIDES: Is he…under a curse?

ME: No.” – Free Range Chickens

Rich became the youngest staff writer ever hired by Saturday Night Live when he signed up for the 2007/8 season and wrote the opening monologue for Seth Rogen’s hosting debut. He stayed on the show until 2011, when he moved to Pixar as a staff writer. Some of his material finally saw the light this summer in Inside Out. All the while Rich was publishing short pieces in the ‘Shouts and Murmurs’ column of The New Yorker. But glory in a sketch show, even one as legendary as SNL, is fleeting, and there’s a niche audience for humorous collections. Could Rich make the same leap as Woody Allen once had, from contributing jokes and writing sketches to longer, more prestigious (i.e. more mainstream) mediums, even if it was just constructing a ramshackle narrative to house inspired conceits?

Inside Out, the 2015 Pixar film which Simon Rich co-wrote.
Inside Out, the 2015 Pixar film which Simon Rich co-wrote.

“‘Chess players are not naturally confrontational. But by the time I entered the number five spot, my opponents were growing bolder. ‘We know you’re cheating,’ they’d say. Or, ‘You’re obviously cheating.’ Or, ‘Please, Terry, why won’t you stop cheating?’” – Elliot Allagash

Rich’s first novel was published in 2010. A novel of scheming and anecdotage (and the anecdotes are mostly about scheming), its tale of a bored teenage billionaire upending his school’s social hierarchy was labelled a Pygmalion riff and optioned for cinema by writer/director Jason Reitman. Elliot and his raconteur father, Terry, have obvious predecessors in Percy and Braddock Washington in F Scott Fitzgerald’s The Diamond as Big as the Ritz, with the innocent John T Unger being reinvented as Rich’s narrator, Seymour Herson. Seymour becomes president after Elliot destroys rivals with schemes that include diabolical exam cheating. But as Seymour edges closer to Harvard, he reaches his limit with Elliot’s antics… To read Elliot Allagash is to want to tell people, verbatim, just how Terry became the Harvard chess champion without understanding chess; what the secret of ancestor Cornelius Allagash’s private club was, and how Elliot took revenge on the restaurant that refused him service. It’s that hysterically quotable.

“Vince swallowed. Lynyrd Skynyrd was God’s favourite band and for months he’d been pressurising his Archangels to somehow reunite the original line-up.

‘I’m not sure it’s feasible,’ Vince said, ‘I mean … half of the founding members are dead’” – What in God’s Name

Rich’s second novel, published in 2012, was reminiscent of Woody Allen’s “early, funny” movies. God gives up on Earth, a disaster from the get-go, to focus on his new project: an Asian Fusion restaurant. But two lowly angels in Miracles Department, Craig and Eliza, win a reprieve. If they can unite a couple who once prayed to be together, God will relent. But they find getting two shy morons to bump into each other again in NYC isn’t enough. Time for ruthlessness: enter Archangel Vince. Rich’s God is a Lebowskian Dude, an amiable big picture man, not good with the computer codes that govern miracles. Rich’s absurdist high concept of Heaven Inc is ingeniously detailed, and more tightly plotted than Elliot Allagash because this is the greatest rom-com you’ll never see. But there’re still diabolical schemes. Vince unleashes one the Allagashes would admire. It involves Regis Kimble, projectile vomiting, and a well nigh unbearably funny Rule of Three.

“Before OkCupid profiles became mandated by the Galactic Government, the only way to find a mate was to self-induce brain-damage and beg strangers for sex in public. The fact that anyone ever achieved sexual congress during these dark times is a remarkable testament to man’s will to survive” – The Last Girlfriend on Earth

Rich’s 2013 collection of sketches and stories, eventually spawned the 2015 FXX comedy series, Man Seeking Woman, starring Jay Baruchel as a hapless everyman dating literal trolls, among other romantic mishaps. Rich’s fertile imagination leapt in Last Girlfriend from a caveman suffering romantic agonies, to astronauts seeking NASA’s permission to study the effect of zero gravity on sex, to archaeological digs investigating the late 20th century mating rituals of Earth One (on which all information had been lost in the Great Google Crash). While using the dating scene as a thematic throughline for stories, Rich displayed an uncanny ability to skewer satirical targets with great economy; whether it was his unnamed Obama feeling the need to weigh in on Otto’s increasingly popular protest against attractive women not dating most men in ‘Occupy Jen’s Street’, or Brooklyn hipsters meeting their downfall when praised by the ‘Sirens of Gowanus’.

A still from Man Seeking Woman, the FXX show adapted from Rich's story collection.
A still from Man Seeking Woman, the FXX show adapted from Rich’s story collection.

“She explains the Gorgons won the war by rounding up all the Narvians and destroying them. All of her friends and family died. I thought we had nothing in common, but now that she’s lost her tribe and I’ve lost Derek, and both of our worlds have come crashing down, I realise we’re, like, exactly the same person” – Spoiled Brats

Rich is a member of Generation Y/The Millennials (or Generation Wuss, according to Bret Easton Ellis). For this self-skewering generation, nothing is funnier than callousness. But Rich’s comic metier in 2014’s Spoiled Brats collection became oblivious callousness; characters so self-involved they’ve not the slightest idea they’re horrible. Rich uses his privileged background to mock with precise detail. But acting as the court satirist of the 1% is combined with furiously logical absurdist scenarios: there’s life narrated by a classroom pet; Santa’s spying elf on a shelf; an over-achieving clan whose individual members kill themselves if they ever falter, and the viral hit ‘Guy Walks into a Bar’, which takes an old joke as the starting point for a millennial riff.

Seth Rogen, Evan Goldberg, and Rich himself are currently adapting the ‘Sell Out’ novella from Spoiled Brats (in which Rich’s life is mercilessly pilloried by his disapproving pickled great-great-grandfather, Herschel) for cinema. If that comes to fruition, or Jason Reitman figures out a way to ditch Hollywood story structure strictures so as not to ruin Elliot Allagash, then Rich’s idiosyncratic comedy will find a far wider audience. With that will come more film and television work, dominating his output. Till then prose comedy fans have the distinct pleasure of his prolific output and unfiltered vision being aimed predominantly at them.


Images via: (credit:Hachette/Melissa Fuller)