Failing Upward, a True Hollywood Story

Is he being facetious? "Probably. I actually have a long, proud history of insulting people who give me money."

However, Hollywood takes a dim view of being made fun of and sees it more like being harpooned, not lampooned. And Hollywood has a habit of biting back.

Stein notes that, while waiting to find out if ABC was going to make his pilot, "Inadvertently, in a back-page column in Time about baseball, I made an incredibly cruel and pointless joke about Mike [sic] Eisner, and somebody who was working on my show pulled me aside and said, ‘You know, Mike Eisner decides whether our show gets on the air.’ And I said, ‘No, he doesn’t. I think he’s a little busy.’

"Apparently, I’m wrong. That’s what he does. I got scared at that moment."

When the show wasn’t picked up, Stein didn’t think his faux pas was the reason. "There was no repercussion at all. People like seeing their name in print." Oh, really?

"I was writing a column about Frenchy [being] expelled from American Idol, when I wrote something that was really cruel about [soon-to-be-fired Fox TV boss] Sandy Grushow by name. Someone said, ‘That’s not smart.’ But I think you can insult anyone because they’ll be gone in a year."

Adding injury to insult, LAT sources tell L.A. Weekly that Kinsley broke with newspaper etiquette and hired Stein without so much as a shoutout to Calendar. Too bad. Because then Kinsley would have discovered what Stein almost proudly told me: that both the LAT and the NYThad previously rejected him as a job candidate.

What happened was that, after stints as a researcher-writer for Martha Stewart Living’s TV show ("I was fired," Stein says) and Time Out New York’s sports editor and columnist ("I was almost fired," he adds), Stein in 1997 was hired by Time’s then top editor, Walter Isaacson, as a writer-reporter. "People were pissed when I got to Time. They thought I was this punk-nosed snot [sic] who was ruining their mag," Stein recalls.

Assigned first to the People page, Stein graduated to question-and-answer interviews, then features, and then alternated columns with Calvin Trillin. After 9/11, Time dropped the column but kept Stein on staff. Still on Time’s payroll but underemployed, was hired by sister publication Entertainment Weekly as an entertainment columnist. The job lasted only eight months. "It was like any breakup," he recalls. "They gave me the ‘It’s us, not you’ line. They were awfully nice about it, considering they fired me."

Enter Kinsley. It took Stein six months to close the op-ed/opinion columnist deal. "I hadn’t had much luck with the Los Angeles Times before that. Back when my E.W. column first got canceled, I talked to [features czar John] Montorio. I talked to The New York Times. But no traction. I had a great track record of people wanting to have discussions with me, and an awful track record of people wanting to hire me."

Much to Stein’s embarrassment, Kinsley admitted to The New York Observer he "had problems" with Stein’s column and didn’t want to "whore after youth" by hiring him. Counters Stein: "It’s not that he didn’t like my writing. I call it a generational difference of opinion. I think people under a certain age like the honesty of the solipsism, and people over a certain age think it’s obnoxious." In truth, the two are Tweedledum and Tweedledee in terms of their smug and detached style of writing.

Stein moves to L.A. in January when he’s finished teaching a class at Princeton. He’s leaving a cushy staff job — he’ll continue with Time as a contributor — for the uncertain future of a freelance columnist. He says he doesn’t even have an LATcontract.

"Yes, it is crazy, it’s not something a smart person would do," Stein acknowledges. "Only someone with a giant, giant ego would do this. I’d be disappointed if I didn’t let myself find out if I’m going to be great at this. You’d think having my columns canceled by most big publications would tell me I’m not good."

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