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Simon Rich, a writer from Oakland, is photographed in his neighborhood in the uptown district of Oakland on April 15, 2013. Rich has written comedy for The New Yorker, SNL, The Believer and various movie studios including Pixar. He will be participating in the The San Francisco Writer's Grotto "Regretature," an evening when authors attempt to exorcise their pasts by reading work that otherwise would have never been public.

OAKLAND -- Simon Rich is neither thief nor spy, but he could be.

The 28-year-old writer, whose phoenix has risen meteorically ever since his college days as president of "The Harvard Lampoon" and right up to his most recent gig writing for Pixar, holds a dynasty in his familial hands.

His father is Frank Rich, former New York Times columnist. His mother, Gail Winston, a HarperCollins executive editor.

But approaching a Telegraph Avenue bistro not far from his Oakland apartment, his literary lineage is incognito. He's a slim fellow in a plaid shirt and dark-framed glasses whose pensive appearance projects no clue of his comic, wickedly wise wordsmith abilities.

And an upcoming stint at Regreturature, a Litquake/San Francisco Writers' Grotto evening at which writers read work they regret having written, is surely a creative caper. After all, it's hard to believe Rich -- the "second-youngest ever comedy writer" at "Saturday Night Live" and an author with five hot-selling books under his belt -- has ever crafted, well, crap.

"Oh, but I had a lot to choose from," he says in an interview last week.

It's hard to tell if he's being earnest or joking, which is half the appeal of his dark-laced humor. Even in conversation, he's sleuthing, looking like a choirboy, but leaving the lingering impression he's parsing the chatter for usable "material."


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At Regreturature, Rich will read an excerpt from The Simon Times, a newspaper he ran in kindergarten.

"The paper was hyperlocal news, and I believe the top story was an incident in which my older brother was chewing gum and blew a very large bubble," he said.

He says the 50-word news flash is a 5-year-old's equivalent to the long-form features he now writes for The New Yorker. He'll read verbatim from the original document, despite the fact that its quality shows he learned to read only days before he wrote it.

"The truth is, the vast majority of what I write, I never show to anybody. After my personal cut, if my best friend, girlfriend and agent aren't in love with something I've written, it's a lot to ask perfect strangers to suffer through it. And I'm not trying to be funny; I'm just trying to be not boring," he says.

Rich's 2013 release, "The Last Girlfriend on Earth," is a series of riotous, Woody Allen-esque jaunts through love and loss. Despite not trying to be funny, he's honed the 32 stories to hilarious minimalist perfection. Rich isn't the first writer to capture all that is comic and infuriating about relationships, but he might be the youngest to do it in so few words.

"I am Oog. I love Girl. Girl loves Boog. It is bad situation," he writes, expressing a lovesick universe in 13 (unlucky) words. "I Love Girl" takes a reader from the story's humble beginnings to a final, sweet/sly love homage with delicious brevity.

As a boy, Rich says watching his parents' "hours and hours" of hard work demystified the job of writing. His fierce desire to become a writer like Road Dahl never waned and a fondness for "The Simpsons" and Looney Tunes burnished his joke-loving tendencies.

"I love (P.G.) Wodehouse, the first 22 pages of "Catch-22," Douglas Adams' "Hitchhiker's" books," he says, rattling off an eclectic list.

Less predictably, nonfiction accounts of extreme circumstances fascinate him.

"I read about life-or-death events like the Titanic, Pompeii, or the Donner Party. My favorite apocalypse is Noah because it's famous."

Due to privacy protection agreements, he can't talk about his work at Pixar, but he's happy to describe his writing habits and the (for-now) hometown habitats he enjoys with his girlfriend and fellow writer, Kathleen Hale.

"I wake up, get right to work, write until noon. After lunch I work until I get distracted by basketball scores," he laughs.

An avid New York Knicks fan, he says the "voices" other writers claim to hear while working are mostly silent for him. Except when he tells himself, "Start working. Stop watching basketball."

After the buzz of writing fades and the final basketball buzzer sounds, Rich and Hale hang out at Bibliomania ("a great little bookstore"), The New Parkway movie theater ("great hamburgers") or aim their walks for rice bowls at Hawker Fare.

"We're pretty boring people," he says. "A typical Sunday is sleeping late, writing for several hours and jogging around Lake Merritt."

Then, predictably, the man The Daily Beast has called "one of the funniest writers in America" steals away, dressed in the perfect disguise: plaid shirt, dark-rimmed glasses, pensive -- and not boring.

SIMON RICH AT Regreturature III
What: Litquake presents Regreturature III
When: Thursday, doors open at 7 p.m., show starts at 8 p.m.
Where: Swedish American Hall, 2174 Market Street, San Francisco
Tickets: $12 advance, $15, http://bit.ly/ZKz2K0
Info: www.litquake.org