It could be easy to dismiss him, if you were snobbish about such things, as just another well-paid multimedia mainstream American humorist.
The youngest-ever sketch writer for Saturday Night Live, he has sold film rights to Judd Apatow and scripts to Pixar. His skill lies in compression – in placing about three ridiculous "reveals" on a page, and not letting you take a breath. His novel Elliot Allagash, about an evil teenage billionaire, was funny and accomplished, but the joke ran dry. He is exactly the right kind of writer for the internet: funny, high-concept, accessible, short, sharable, a James Thurber for the Twitter age. Now that you don't need a paid subscription to access them, a lot more people are reading Rich's stories online. Many of these stories, including the penis/pianist one, have appeared in the New Yorker. ("He was just so adorable, with his pentagram birthmark and little, grasping claws.") In "Gifted" an oblivious New York woman gives birth to a devil and has him placed on medication for ADHD. In "Guy Walks into a Bar", a bartender with penile dysmorphic disorder ends up with a foot‑tall pianist after asking a genie for a 12-inch penis. In another, a chimpanzee talks about the time he visited the White House. There is a story set in the year 3014, about a self-absorbed girl who goes into space and misses her indifferent boyfriend. But in these new stories the surrealism has been upped a notch. He once narrated a poignant love story from the perspective of a condom in a boy's wallet, for instance. Rich has always been a writer with an eye for the surreal. He stacks surrealism on top of slick satire on top of pure childish silliness in such a brilliant and condensed way, there are sometimes three laugh-out-loud moments within the same paragraph. He can conjure authentic, from-the-abdomen laughter on almost every page. The good news is that Simon Rich, the real one, is very much laugh-out-loud funny. Simon moans into his hands like a man who has lost his family.
"Well … maybe it's not laugh-out-loud funny … " Eventually, she looks up from the screen.
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