The Adventures of Maer Roshan, Editorial Boy Wonder

The former Radar editor bounces back from rehab with a new website, The Fix, and a top-secret iPad project called Punch.

Mr. Roshan’s first serious dalliance with magazines occurred in the late 70’s, and it seems to have made a powerful impression. He was a Jewish kid growing up in prerevolutionary Tehran, the son of a Persian-Jewish father and an American mother. The Roshans subscribed to Time—but their issues inevitably arrived late and incomplete.

“I don’t know how they found the time to do this,” Mr. Roshan recalled, referring to the Shah’s regime, “but they would go in and cut out everything they didn’t like, so you’d get magazines with whole articles missing.” Tidy though it sounds, Mr. Roshan’s subsequent career can be seen on some level as an ongoing campaign to shovel copy, the more provocative the better, into those mysterious blank spaces.

This did not always please Radar’s various backers, who might have wished he held certain of their sacred cows in higher regard. During my tenure, Hillary Clinton was the most sacred of all (Bill was, at the time, a frequent flyer on Mr. Burkle’s 757, “Air Ron”). I recall one dramatic showdown over a fairly tame web roundup of Hillary’s “cronies.” The story ultimately ran, but at some cost to Mr. Roshan’s relationship with our funders.

“Some would say it’s a little reckless but he does what he believes in,” noted Mr. Tennant, who pointed out that Mr. Roshan had gleefully alienated the gay mafia with “Trophy Boys” just when he was set to become a made member. “He could have been sipping Cosmos at Calvin’s beach house!” Mr. Tennant said. “And it would probably more advantageous not to put Courtney in The Fix. But to his credit, Maer is always ready to absolutely piss someone off.”

“If I’d been more willing to compromise, I probably would have gotten a lot further,” Mr. Roshan conceded.

Another formative and cinematic memory: It’s the Fourth of July at the Community School in Tehran, an academy for the children of American expats. As Maer and his schoolmates look on awestruck, a helicopter buzzes into view and hovers over the school’s courtyard, whipping up a swirl of dust. The chopper’s door slides open. The children raise their eyes to the blue sky, and McDonalds hamburgers rain down.

Meanwhile, demonstrations against the Shah were gathering steam: fevered protest marches passing right outside the school’s gates, guys beating themselves with chains, tanks rumbling in the streets, people throwing rocks and lighting piles of garbage on fire.

In 1979, Mr. Roshan’s mother whisked him and his two younger brothers back to her parents’ house on Long Island while his father stayed behind to deal with the family’s property. The Shah’s puppet government soon fell, and Ayatollah Khomeini was swept into power. Mr. Roshan’s father escaped seven years later, but the once-colorful figure was diminished. He died of cancer within a year.

After arriving on Long Island, Mr. Roshan’s mother set up a flea market booth at Aqueduct racetrack, peddling $3 belts to make ends meet. Somehow she eventually earned enough to buy a house in Five Towns and to send Maer and his brothers to an Orthodox yeshiva. Though he wasn’t religious and already knew he was gay, he seems to have fit in well. His second year, he ran for vice president of his class, and despite having to deliver his Hebrew campaign speech phonetically, he won.

Before long, he was zipping into town on weekends with a female friend to hit the nightclubs he’d read about in New York and Interview. Their first such excursion was to Area. The high-schoolers took one look at the crowd outside and quickly determined that standing at the back of the line would never do, especially if they wanted to be home for curfew. Instead, they planted themselves at a distance from the scrum in front and pretended they didn’t want to go in at all. “The bouncers were like, ‘You,’” Mr. Roshan recalled incredulously.

Inside, the theme was Religion. A guy was hanging from a cross. There was a pool of fire on the dance floor.

Mr. Roshan attended N.Y.U. as a journalism and politics major and got to know club kids Lisa E. and James St. James. Dressing for a night out was a two-and-a-half-hour process and often involved the company of a posse of drag queens. Asked to describe his look at the time, he said merely, “I wouldn’t want those pictures to surface, that’s for sure.”

After a short stint in Key West, where Mr. Roshan covered the police beat for a local paper (making sure to boldface the names in the crime blotter), he became an editor at Interview. His first article to cause a stir was a freelance piece, an exclusive Q&A he landed with Liz Smith for Outweek, despite the fact that the magazine had excoriated her for months over her refusal to come out as a lesbian. “I was being attacked constantly!” Ms. Smith recalled. “But Maer was so convincing. I honestly don’t know how he did it.”