The Jong-Fast Family

If they squint, the extended Jong-Fast clan—a family of artists, writers and wild-child red diaperlings—can trace their history all the way back to the father of Yiddish literature.

“Sholom Aleichem is the oldest possible relative that Grandpa claimed,” said Molly Jong-Fast, the 28-year-old writer. “There’s some story about that, that he was related to Grandpa Howie.” (“Grandpa Howie” would be the novelist-cum-communist Howard Fast, for those who don’t know.)

It was shortly after 11 on a luxe Upper East Side Tuesday, and the young Ms. Jong-Fast was perched in an armchair in her mother’s dining room. That mother is the writer Erica Jong, author most famously of Fear of Flying, the 1973 novel that helped shake a generation of repressed little lassies out of their zipped-up skivvies. Now 64 and happily settled in an art-filled East Side apartment, Ms. Jong appeared as blond and saucy as ever as she plumbed her family’s history, tag-teaming her daughter’s sentences in a game that often felt like a kind of six degrees of Sholom Aleichem.

Name a Jewish literary or artistic figure and they would find a connection; even choose a businessman and, most likely, they would trace a link. For instance: the novelist Jonathan Fast? That one was easy. He is the young Ms. Jong-Fast’s father, her mother Erica’s former husband and the son of the aforementioned patriarch, Grandpa Howie.

How about the gossip queen, and second Ron Perelman wife, Claudia Cohen? She is the younger Mr. Fast’s first cousin via his mother Bette’s line—a line that began with Isaac Cohen, the founder of Hudson County News Company (and a man whom Ms. Jong described as “one of these tough little Jews”).

Or what about—for a real challenge—the French Impressionist Camille Pissarro? Pissarro was born in St. Thomas in 1830, the son of a Dominican mother and Sephardic Jewish father, and spent most of his life in France. But trace down a few generations and a good 100 years, and it turns out that Ms. Jong’s niece, the artist Annabel Daou, happens to be married to the Impressionist’s great-grandson, MoMA curator Joachim Pissarro. The separation is exactly six degrees.

A family stacked with so many movers and machers offers plenty of perks to its lucky members: rich family lore, enviable connections, entrée to editors, to say nothing of grist for the next big novel. In a way, it’s like living in a modern-day shtetl, an upscale one, where everyone just happens to live on the Upper East Side, or maybe Upper West, where the floors are covered with fine Persian rugs instead of dirt, but also where the sprawling, honking insanity of New York seems suddenly to contract to a few narrow streets, a handful of industries which are at once cozy, familiar and approachable.

“It’s like mishpucha,” said Susan Shapiro, author and young cousin of Howard and Bette Fast, recalling how, when she arrived in New York in 1981, Howard Fast took it upon himself to introduce her to the various literary luminaries at one of their famous parties.

“He would say, ‘This is Suzy Shapiro, she’s a new brilliant writer in town, you better be nice to her, she’s mishpucha,’” said Ms. Shapiro, whose upcoming book, Only as Good as Your Word: Writing Lessons from My Favorite Literary Gurus, includes a chapter dedicated to her favorite cousins. “And what was interesting was that, when Molly was 14 or 15 and she was hanging out with my New York Times editors and everything, I heard myself say, ‘Molly Jong-Fast, brilliant young writer, you’d better be nice to her, she’s mishpucha.’”

“A family like ours is like a relic,” Ms. Jong-Fast said as she nibbled on a chocolate rugelach.

But if the shtetl model has its advantages, it also has its complications, intrigues and odd love triangles—or perhaps even rectangles, like the one that saw Ms. Jong’s fourth and current husband, the divorce lawyer Kenneth Burrows, briefly dating her former husband’s older sister, Rachel Fast. It was a long time ago—when Mr. Burrows and Ms. Fast were barely adults—but it apparently caused serious consternation in the Fast household, because Mr. Burrows’ uncle, the famed playwright Abe Burrows (think Guys and Dolls), had been a “turncoat” who talked to “the Committee”—that would be the House Un-American Activities Committee—while Howard Fast had refused and been blacklisted.

“It’s pretty incestuous,” Ms. Jong said with a throaty giggle.

Incestuous and, for all its free-to-be-you-and-me bohemianism, perhaps a little demanding, too. After all, the Jong-Fasts are the product of at least four self-made immigrant storylines, and a family doesn’t produce more than three generations of writers and artists without a serious myth system pushing them forward.

Peter Daou, the club-scene musician turned political blogger, who also happens to be Ms. Jong’s nephew via her older sister (and co-author of the album Zipless, inspired by his aunt’s poetry), was inclined to put a benign spin on it: “There was always a sense of ‘Make something happen, but do whatever you feel passionate about,’” he said of his parents’ child-rearing philosophy. “So it’s a combination of wanting to be overachievers and having the freedom to do whatever you want.”

But Jonathan Fast, who grew up under the shadow of a man who wrote more than 80 books, many of which were adapted for television and film, recalled something more direct—a mantra, even—woven into the red diapers: The only way you can make a living is as a writer.

“It was just what [my father] said, and then my mother used to agree with him,” said Mr. Fast, 58. “It’s insane—I still believe that.”

His onetime wife, Ms. Jong, recalls growing up with a similar notion in her family, where it seemed that everyone—save, perhaps, her importer-exporter father—was walking around with a smock, paintbrush and deep artistic thoughts.

“I guess I always had the feeling that, ‘How could you make a living if you weren’t an artist?’” Ms. Jong recalled.

To which her daughter responded: “Little did we know that they were like the five people who could do that!”

With two books already under her belt, Ms. Jong-Fast would seem to be the next in line to inherit the familial writing mantel. But if you ask her, she’s not always sure she wants it. She has settled down now, had a child, joined two temples—a far cry from her mother’s early husband-swapping, city-hopping ways.

“I think, had I been a little bit more away from my particular peccadilloes, I think I would have been a doctor,” the daughter said. “I really wanted to be a scientist or a doctor.”

There was a flicker of confusion on her mother’s face. And then, with a phrase repeated by generations of Jewish mothers, famous or otherwise, she said: “You know, Molly, it’s not too late to be a doctor if you want to be a doctor.” The Jong-Fast Family