Good misfortunes

Hollywood understands failure. The entertainment business needs it, on a fundamental level. That’s how it works here: You fail and fail and fail until, finally, you either make it or you give up and go back to a normal life.

Bragging about failure, on the other hand, simply isn’t done. When you work in an industry that lives and breathes disappointment, you don’t want to be reminded that failure stalks you like a shadow.

The exception to this rule is Toby Young, a 42-year-old British author, playwright, theater critic, occasional actor and self-proclaimed professional failure who came to town recently with a Hollywood memoir to flog, determined to wrench some success out of what’s been so far a dismal flirtation with the film business.

“The Sound of No Hands Clapping” is Young’s sequel to his bestselling 2001 memoir, “How to Lose Friends & Alienate People,” which chronicled his ignominious demise at Vanity Fair magazine in New York, where he was a contributing editor from 1995 to 1999. The follow-up finds Toby moving to L.A. and trying to fulfill a “lifelong ambition” to become a screenwriter.

Things pick up roughly where “How to Lose Friends” left off. It’s 2000, and Young is trying to persuade his girlfriend, Caroline Bondy, to marry him. He’s scratching out a meager freelance existence. In due course, Bondy says yes, the first book is published, a baby girl arrives, and the Hollywood seduction begins.

Together, these memoirs summarize why Young has become a strange kind of media-world figure, widely (and sometimes justifiably) loathed and mistrusted, but somehow always given semi-respectful attention. It’s a reaction to his craven yet unapologetic lifelong pursuit of fame and all its gooey trappings.

So far, however, his stunted celebrity has resulted mainly from screwing up, often in spectacular fashion. Failure is his Elysium. But as he sat poolside at the Standard hotel on Sunset Boulevard last week, explaining his new book and his dreams of coming back to L.A. at some point to take Hollywood by storm -- the current plan involves some kind of small film success in England first -- he was a picture of amiability. Enthusiastically talking about everything from Oscar Wilde to his late father, he nursed an iced latte and adjusted his rimless sunglasses.

As he spoke, a tree pruner hacked dead fronds off a nearby palm, raining dust across the pool deck. Unfazed by the mess as well as the Nathanael West-grade symbolism (dead wood? If it were an omen, could it be so very obvious?), Young vigorously brushed the dust off his laptop.

An Oxford grad and Fulbright scholar at Harvard, Young joined forces with British journalist Julie Burchill in the early 1990s to launch the Modern Review, a publication that sought to tweak the intellectual establishment by focusing highbrow brainpower on lowbrow topics. It folded acrimoniously in 1995, at which point Young, who had gained a following in New York, was invited by Vanity Fair Editor Graydon Carter to join the magazine on contract. After a series of screw-ups that at times seemed suspiciously calculating, if consistently audacious -- asking Nathan Lane in an interview if he were Jewish and gay, ordering a strip-o-gram for a colleague on Take Our Daughters and Sons to Work Day, harassing celebrities at the Vanity Fair Oscars party -- Young was cut loose, at which point he returned to London. He wrote “How to ...” and later turned it into a play.

In 2002, he received a completely unexpected call from a noted film producer, referred to as “Mr. Hollywood” in the new book (Young refused to name him on the record; he said it was out of fear of physical harm). Mr. Hollywood commissioned Young to write a screenplay for a biopic. Young decided his future lay in becoming a Tinseltown scrivener. He borrowed against his house and in 2004 journeyed west with his exasperated bride and his baby daughter, Sasha.

He lasted three months.

He vows to return. “I love it here,” he declared.

Students of Young’s enthusiasms know he has long been a champion of what he terms genre entertainments. Not for him the pretentious Euro-flick; he prefers good old Goobers-and-popcorn American fare. Having abandoned -- or assassinated, depending on your perspective -- his hope of becoming a top magazine editor in Manhattan, Young has recalibrated his reckless ambition. His current objective is, despite the humiliations described in “The Sound of No Hands Clapping,” to “write, produce and direct” a movie in England, then return to Hollywood and assume his rightful place as a screenwriter in the mode of Ben Hecht and Preston Sturges. “I’ve learned that the best strategy is to become a big fish in a small pond,” he said. The flicker of sunlight off his balding head matched the determined glint in his eyes.

“I’m not going to fail this time,” he announced, leaning across the table, jabbing it with his finger.

No one needs to brief Young on the sordid history of aspiring Hollywood screenwriters. He has read all the books. He has also been cordial with Rob Long, highly quotable conservative Tinseltown insider and periodic television producer, for years (Long’s advice figures prominently in “The Sound of No Hands Clapping”).

But life with a view of the Pacific and a copy of Final Draft on his PowerBook appeals to him in a way that, up to this point, nothing else has. Although at a recent panel discussion at Barnsdall Art Park, sponsored by the Los Angeles Press Club, Young confessed that he never totally switches off the journalist within. No one in attendance, including co-panelist Long, was surprised.

Nor should they be. The journalist in Young knows that his reputation as a bumbling failure, amusing in a sort of royal-fool way back East, doesn’t play in the American Dream Factory. It’s time for a new identity, one that will fly better here. (This might be why the new book has thus far received more tepid reviews than the first, in spite of being pretty funny: The first raised hackles and had tough-talking Vanity Fair Editor Carter at its core; the sequel has a tolerant wife and the birth of his son.)

Still, he may have a few more tricks in his bag. For example, he places tremendous stock in his DNA. He believes he has a genetic advantage over the competition. Daffy as it may sound, he has a case. His father, Michael, and mother, Sasha Moorsom, were legitimate British postwar intellectuals. Michael Young famously coined the term “meritocracy.” Moorsom was an artist. Visions of an updated, Kingsley Amis-era Bloomsbury dance in your head. When they were alive, Toby’s parents expressed mild displeasure at his career choices; they would have preferred an academic path or a more serious category of journalist (foreign correspondent, for example). But they groomed his mind, ensuring that their fame-starved son would at least possess a gift for making complex topics easily digestible, by virtue of a lucid prose style.

He may have ignored their advice, but his parents’ influence has been an obvious guide to Young’s decision-making. “It dawned on me after everything went horribly wrong in New York that I had to completely reevaluate my persona,” he said. “Otherwise, I was going to end up a homeless drunk.” That led to his marriage, children and, for him, a midlife reckoning. “I would say that I have, um, mellowed with age.”

Young’s resilient genome, however, does not appear to have diminished the ambition level of his scheme to retake Hollywood. This might be because, as he has failed and failed and failed some more since leaving college, he has also seen plenty of other promising ... well, meritocrats, slip down the greasy pole to obscurity. When asked about one budding New York media player who disappeared from the scene several years ago, Young made no bones about the guy’s problem: “He didn’t have my dad.”

Next time around, Toby Young stands a very good chance of failing more miserably in Hollywood than he did last time -- or worse, of being simply ignored. But his faith in his destiny remains unshaken. He is Patton-esque. His aspiration is to, as he puts it, “create a lasting work.”

His friends believe he can pull it off.

“When Toby sits down to write the script he wants to write, rather than the script he thinks someone wants to read, then he’ll write a great script,” Long said. “Right now, he just doesn’t trust his instincts enough.”