Pain and Pleasure and Guilt, Oh My!

Late last Saturday night, a thin strip of indoor/outdoor red carpet led from the parking lot of the Magic Castle in Hollywood to a small, close-ceiling function roombehind the glamorous house of tricks.

Inside, 100 or so young Jews gathered to celebrate the third issue of Guilt & Pleasure, a literary quarterly out of New York whose first issue featured a cover photograph of a border collie smoking a cigarette. Stacks of the summer 2006 issue lay about, but it was too dark in the small, nightclub-like space to read anything but the turquoise-colored title: “The Magic Issue.”

A bar anchored the back of the narrow room, featuring no-host, all-you-can-afford $10.50 cocktails, and several rows of folding chairs faced a teensy stage.

The young man next to me, a writer with darkly alert eyes and a sardonic smile, said the magazine serves a young, hip, intellectual Jewish audience “not quite being served” by Heeb, another magazine out of New York.

It seems to me the distinction is perhaps the Gen Y equivalent of the differences among the AJCommittee, AJCongress and the ADL — that is to say, indecipherable to outsiders. As near as I can tell, both publications are aimed at young Jewish men with darkly alert eyes and sardonic smiles, and the women who hope to marry them.

All around me were plenty of examples of both: dressed up (the Magic Castle has a coat-and-tie policy, even in its dungeon), animated and about as cool as Jews who aren’t Leonard Cohen can possibly be.

The emcees, Jill Soloway and Jessica Chaffin, took the stage, having won the thankless job of trying to figure out exactly what kind of Jewish jokes would make these particular Jews laugh. Both were trying hard for laughs, which of course is the death of cool.

They brought on the magician, Andrew Goldenhersh, who looks like Rasputin but otherwise seemed very nice. He held two raw eggs, had volunteers strap him into a straight jacket, and said he would wrestle his way out without cracking the eggs. When he had freed himself, he reached inside the white coat and pulled out two fully alive chickens.

It was brilliant, but that’s not magic, of course; that’s tricks.Out came a contributor to the issue, Gregor Ehrlich, who read his essay on how his life has intersected with the lives of various chickens. After a few very dry, very sardonic minutes, a heckler called out, “What’s this about?”

“It’s about chickens,” Ehrlich said — unflappable — and continued.

Indeed, what is it about?

Ever since national studies back in the 1990s showed a marked decline in the numbers of young Jews affiliated with Jewish life, along with a rise in intermarriage rates, Jewish professionals and the foundations they hit up have made it a priority to captivate this precious demographic — aka, the future of our people.

No one knows what works, so everything gets a try. Salons? Here’s a couple grand. Yiddish rappers? Here’s another thou. Leadership seminars in a snowy resort town? Here’s $100K.

Both Guilt & Pleasure and Heeb are nonprofit publications that required substantial donations to get them going and keep them afloat. The former distributes 20,000 copies of a 154-page, four-color journal on heavy stock. That’s a lot of cholent for the poor. Heeb received its tens of thousands from foundations established by Andrea and Charles Bronfman and Steven Spielberg, and G & P has tapped many of the same resources. The idea is that publications will reach and give voice to a generation of Jews otherwise cut off from their roots, thus drawing them back to the fold.

They cost a lot. But do they work?

There is no hard evidence. But the media echoes Heeb produces make Judaism palatably hip to the youth market, at a time when Israel, that other noticeably Jewish product, has been less than beloved by college kids. And every Jewish generation needs a safe place for its intellectuals to play among themselves, whether it was the original Yiddish Forverts or Commentary, Lillith or G&P.Back at the Magic Castle, the comedians finally took hold of the night.

Jeffrey Ross, a standard fixture at celebrity roasts and my favorite un-famous comic, got up and killed. He insulted the venue — “I had to put on a tie for this s—hole?” — insulted the organizers and insulted the audience.

When he called the cheeky Times columnist Joel Stein “just like Tom Wolfe, but without the talent,” some in the audience gasped at the audacity, because Stein, like Jon Stewart, is Jewish hipster royalty — the court jester with mainstream media exposure. Plus Stein was sitting in the front row. (No worries, he has a sense of humor.)

Ross got big laughs with well-told Jewish jokes. “The other night my girlfriend and I rented a Jewish porn movie,” he deadpanned. “It was called, ‘I Don’t Do That’ … which I think was a remake of ‘Eeeew.'”

Rewind 40 years, clean it all up a bit and you’re back in the Catskills.Same with the next comedian, Jeff Garlin. The co-star of “Curb Your Enthusiasm” turned out to be a real Falstaff in the faux-English venue, one-upping Ross in viciously insulting the hosts, the Castle, the audience, then improvising a set that ranged from anti-Semites trying out their accents to comedian Dane Cook.As I left, an embarrassed magazine promoter pulled me aside. “Write about the magazine,” he said, “not the evening.”

OK: Guilt & Pleasure is good, often very good, and the magic issue is its best.But the evening wasn’t all bad, either.

What seemed to work was what Ross and Garlin did, which, really, was the stuff that worked for Mason and Rickles and Groucho, and no doubt for generations of tummlers and badchanim before them. Insults. Self-deprecating humor. Mockery. Screwing with the status quo, even when the status quo are hip Jews who think they’re the ones screwing with the status quo.

Every generation of Jews thinks it is the revolutionary one, the one that will upturn the traditions and set the old ways. But we are a people with a long, valued tradition of invective and obstreperousness. This week’s Torah portion makes a point of singling out the wayward son for punishment, but centuries of rabbis afterward found a way to soften the harsh decree, and bring him into the fold.

The strength of Jewish culture is its ability not just to give birth to its own critics, rebels and jesters, but to set an honored place for them at the table. To think there is a status quo that Jews will not attack, or to think any one generation is the first to attack it — now, that’s illusion. l