In 1994, I came in from the freelance-writer cold and took a job at Newsweek. I spent the next four-plus years there, followed by two and a half at the New York Times before I wrapped up my career in legacy media to write a book and try to make it in Hollywood. Not a decision I regret, but one I look back on with a mixture of nostalgia and amazement that print journalism still meant something back then—even if it didn’t mean quite as much as it thought it did. I caught the very last of those halcyon days when it was still, above all else, fun.

I’d had regular gigs before. After graduating from Columbia’s School of Journalism, I interned for a year at Harper’s magazine, under Commentary’s own Terry Teachout, who was at the time a senior editor and the magazine’s token conservative. I toiled on an electronic typewriter in a windowless broom closet across from the upper-masthead guys. Eric Etheridge, an affable young Mississippian, always seemed buried under the data he culled to produce the popular Harper’s Index. Down the hall were Gerry Marzorati, who moved in rarified literary and art-world circles with an aloof stylishness I coveted, and Michael Pollan, who was nice to everyone and, most impressive to me at the time, the brother of Tracy Pollan, who played Michael J. Fox’s girlfriend on the sitcom Family Ties. Everyone would go on to bigger and better. Pollan became a bestselling author of books on gastronomic, then psychedelic, science. Our intern was Fareed Zakaria, now chief foreign-affairs pundit at CNN.

The editor in chief who led the magazine’s ’80s revival was Lewis Lapham. He defined intellectual shabby chic, banging out his contrarian columns on an old manual typewriter while fending off creditors. Born into old San Francisco money that must have evaporated, he was supported by a rich wife, yet always seemed on the verge of ruin. His life was very Bonfire of the Vanities, which came out the year I was there (1987). But he pulled it off with panache, an Elaine’s élan, and a resonant smoker’s voice. He once signaled his disdain for a piece I’d championed by tapping ash from his cigarette on its cover page.

I sensed it was time to move on.

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I ’d been supplementing my $14,000-a-year Harper’s salary with a little freelancing on the side, for the American Spectator and the Washington Times. That riposte to the Washington Post, owned by Sun Myung Moon’s Unification Church, had offered Terry a job as its TV critic. Too lowbrow for him, but he suggested me. So my new bride and I (it was a whirlwind Harper’s romance in which my Toronto-born need for a green card played a role) moved to D.C. There I learned to crank out pieces on a daily deadline—an invaluable skill I’m still grateful for today.

The editor in chief was a suave, perma-tanned Belgian named Arnaud de Borchgrave. Arnaud had been Newsweek’s Vietnam correspondent and had a Murphy bed installed in his office alongside uniforms of various foreign militaries, readying him on a moment’s notice to be “wheels up” to some global hot spot. Despite his exotic journalistic pedigree, Arnaud was no snob. Unlike the insufferably elitist New York Times poohbahs I’d encounter later in my career, he read the whole paper front to back. If he liked one of my TV reviews, I’d get a handwritten attaboy on one of the yellow note cards he sprinkled the newsroom with. We called them “Arnaud-grams.”

Our Life section was a four-color confection of soft features, gossip and reviews enriched by some serious talent. David Brooks was the movie critic. Pop music was the domain of David Mills, a talented black reporter who made national headlines calling out the anti-Semitism of the rap group Public Enemy. Mills later segued into TV with his old Baltimore Sun colleague David Simon on a series called The Corner, the precursor to The Wire. (He’d win an Emmy later and die tragically of an aneurysm on the set of Simon’s show Treme at the age of 46.) Malcolm Gladwell worked at Insight—a newsweekly published on the mezzanine floor of our big open newsroom, which had a wall of windows on the Washington Arboretum. Full disclosure, the Life section, then Insight, were run by Commentary’s current editor, John Podhoretz, who was for three years my boss until a broken marriage and career restlessness led me back to New York. I’d contributed a couple of pieces to Spy (for my fellow Canadian Graydon Carter) and decided to see whether I could make it as a full-time freelancer.

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Armed with a mini-cassette tape recorder and a stack of “Reporter’s Notebooks” (both items that could now be relegated to the Smithsonian), I operated out of a fifth-floor walk-up on West 25th Street in what I called “The Sewing Machine Repair Shop District.” From my Newsroom of One, I set out to be the most prolific writer in New York. At my peak, I published a hundred pieces in a year. Covers for TV Guide (which paid the best). Features for GQ, Vogue, Condé Nast Traveler. I did “The Rolling Stone Interview” with Howard Stern, and an Interview interview with his sidekick, Robin Quivers. I Jet-Skied with Vanilla Ice, wrote a monthly advice column on men for Mademoiselle under the pseudonym Jim Dixon (in tribute to Kingsley Amis). My mantra (stolen from S.J. Perelman) was “Faster than anyone better than me and better than anyone faster than me.” I didn’t have much trouble getting assignments because I delivered clean, on-time copy with no drama. Of course, there were long nights of angst and schadenfreude and other German emotions. Why couldn’t I crack the New Yorker? Why wasn’t I making $5-a-word? Who was making $5 a word?

I drowned those glossy sorrows with $4 bottles of Beck’s at my Elaine’s, a dive called Billy’s Topless. I might still be there, if they hadn’t torn down Billy’s to put in a bagel place. And if Newsweek hadn’t come calling.

Time’s perennial competitor hired me as a “general editor” (which meant writer) to cover TV and pop-culture for the Lifestyle section in what was known as “the back of the book.” I got my own office (remember offices?) with my name on the door. I wore a jacket and ’90s skinny tie to work. That was not mandatory, but I was so elated to have a job that I enjoyed looking the part. My boss was a mensch named John Capouya, who’d come from Newsday, the Long Island–based paper. The son of an academic, John looked like a bearded Richard Gere, had a pigeon-toed basketball-guy walk and a laid-back vibe. He, too, seemed happy to have escaped the ink-stained trenches of newspapering for a world of weekly, not daily, deadlines that allowed plenty of time for long expense-account lunches.

Our regular haunt was Gabriel’s, a high-end trattoria on the north side of Columbus Circle. Half a dozen of us from the Lifestyle and Business sections would eat, drink, and do what journalists love to do most: gossip. As in, complain about our superiors, the so-called Wallendas who ran the magazine. When the bill came, someone’s corporate card came out, and we paid sardonic lip service to our benefactors at the Washington Post Company and the Graham dynasty that controlled it and owned Newsweek. Then we made our way back to the office around 3 o’clock and pretended to work until the whistle blew. I can still taste that mushroom risotto.

This was not pure idleness. There really wasn’t much for the writers and editors to do until the end of the week, when the magazine “closed.” Like Time, which invented the form, Newsweek ran on a caste system of “reporters” and “writers.” The reporters would run around interviewing people and compiling research that they would present in a voluminous “file” to the writer. The writer condensed the file into a zippy, readable number of “columns”—the unit measure of a story, depending on the size of the piece. For our section, that happened on Fridays (Saturdays for the newsier “front of the book”) and meant sticking around for dinner on Friday nights while the Wallendas had their way with your copy. And by dinner, I don’t mean random take-out orders wolfed down at your desk. I’m talking a full catered meal in the Newsweek dining room. At Time, a drinks cart used to make the rounds on closing nights. Allegedly at Newsweek too, but by the time I got there, the magazine had moved from Madison Avenue to Columbus Circle and left some of its louche Mad Men customs behind.

Friday nights could go late, so town cars were provided to see staffers home safely. I liked to push this privilege. As I mentioned, I’m fast. One night, I’d polished off my piece early and there was a party for a ’zine (another bygone artifact) called Paris in the 20s whose supremely dry form of journalistic satire was to excerpt verbatim ridiculous bits from the New York Times. As a single guy always on the lookout for female fans of dry journalistic satire, I didn’t want to miss the party. So while my colleagues sweated their deadlines, I took a town car downtown, hung out for an hour, then called another car to bring me back up to Newsweek to close my cover story on The X-Files or South Park or JFK Jr.’s girlfriend or whatever it was that week. No one batted an eye. Emboldened, I pushed further. One summer, I had a “share house” in the Hamptons, so come Friday night, I took a car service the full two hours from Manhattan to Sagaponack. 

In all my time at Newsweek, no one questioned an expense. On the contrary, my editor, Capouya, once called a staff meeting and scolded us for not using our expense accounts enough: “How are you gonna get story ideas if you don’t take anyone out to lunch?” Actually, he didn’t scold all of us. Apparently, I was the only one of us blowing sufficient quantities of Post Co. dough every month: “Now Rick here is doing it right.” I suggested we lunch at Gabriel’s to discuss.

A final note about the largesse that made Newsweek such a collegial place to work: Any work-related flight over three hours, you flew Business. Not until I got into TV and joined the Writers Guild would I again enjoy flying “warm-nuts class” on someone else’s dime.

As long as you filed on time, Newsweek didn’t care what other action you had going on the side. I used to do regular movie reviews for CNN on air, for which the magazine even threw me a $100 honorarium, $50 for a radio interview. Hey, I was promoting the brand! I also picked up extra cash from celebrity profiles here and there. One was of the actress Andie MacDowell for Allure, Condé Nast’s beauty bible. The editor who threw me the piece, Ilene Rosenzweig, would soon have a major impact on my career—and my life. The New York Times hired her as deputy editor of its revamped SundayStyles section. She convinced them to hire me.

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At Newsweek, I’d enjoyed commanding views of the Manhattan skyline from my 17th-floor office. At the Times, I was ushered to a grimy cubicle on the windowless third floor next to my editor, Trip Gabriel, and across from his deputy, Ilene—who had, in the ponderous interim between being considered for a position at the Times and being hired for said position, become my girlfriend. Management was aware of our relationship and, to avoid conflict of interest, deemed with Solomonic wisdom that only 49 percent of my stories could be for SundayStyles. The rest would be for Home, Dining, the Arts, wherever else I wanted to write. This Talmudic rule, like many at the Times, was never enforced. But Ilene, in her sauciness, liked to tempt fate by trying to make out with me whenever we were alone in the elevator, waiting until the doors had started opening to cease her molestation. As girlfriend-editors go, I give her high marks. Ilene was the one who sent me to L.A. to hang out at the Playboy Mansion. When you’re lucky enough to find a woman like that, you have to marry her. A few years later, I did. We now have two kids and a dog.

The Style Department shared the third floor with Sports—unlikely bedfellows. Someone in Sports was always holding a phone in the air and shouting, Anyone for Bustaaah?! As in Buster Olney, the baseball columnist. The boxes of half-eaten pizza they always seemed to have over there may have explained the mousetraps under our cubicles.

One of the reasons SundayStyles was so popular was the wedding announcements. My proximity to the Keebler Elves who put out this antiquated social diary every week made me a hero at a friend’s wedding. It was a Friday evening, and before I left for the rehearsal dinner, I asked the Copy Desk if I could peek at one of that Sunday’s entries. Sure enough, there was my friend’s name, his bride, and a brief account of their romance—below a picture of two completely different people. I asked for a page proof of the botched announcement and took it to the dinner. After letting the bride die a thousand deaths inside—she and her mother had waited their whole lives for the validation of a wedding announcement in the Times—I announced that I’d saved the day and fixed the mistake. I also spared the offending copy editor a public flogging in the Times’ dreaded Corrections box.

The Copy Desk, manned by long-suffering lifers, was low-hanging fruit for mockery and abuse. Its staffers were zealous guardians of all things “Times-ian.” I was once denied the word “addled,” because in some long-lost medieval etymology, it was considered a synonym for urination. It wasn’t really their fault. They were merely the lowest receptacle of the self-regard that trickled down from the top.

When Howell Raines was promoted to the job of executive editor, his predecessor, Joe Lelyveld, led him on a tour of the newsroom. As they stopped in the Style Department, I overheard Lelyveld tell Raines to take a good look around, because it would be the last time he’d be setting foot in here. We were fluff, they were news. Never mind that we actually made the paper money—our section was fat with ads—and that it would be Raines who disgraced it with the hiring and promotion of a plagiarist named Jayson Blair.

The struggle against pomposity at the Times was real. Any time I pitched a story, I’d be challenged to ensure its Times-worthiness. Like when I pitched Larry David. My final cover story at Newsweek had been on the last episode of Seinfeld. I’d spent 10 days on the set, most of it kibbitzing with Larry, the show’s co-creator, who was vastly more entertaining and pleasant than the weird and standoffish Jerry Seinfeld. So when HBO gave Larry his own show, I suggested a profile. This notion was met with extreme skepticism from Trip, my editor: Hmmm. I don’t know. Larry who? I prevailed. Curb Your Enthusiasm has run for the past 20 years.

For all its stuffiness, there were still some classic, old-timey characters around the place. The mail carts were pushed by ancient pressmen in white smocks, whom technology had rendered redundant but whose union made unfire-able. I loved Mort, the photos guy, who wore huge black horn-rims and dropped Catch 22–isms such as “FUBAR” and “SNAFU” as he hurried about his business. When I did my first (and last) Page One feature—a dispatch from a convention of stay-at-home dads—I was presented with the metal plate used to print the page.

Another great thing about the Times: Everybody returns your call, no matter how dumb the story. I was reporting a trend piece on the complexity of male greetings: the dap, the fistbump, the bro hug. I’d heard that Donald Trump, then a mere real-estate mogul, was a major germophobe, so I put in a call to his office. Within seconds, he was giving me his take on how to glad-hand without physical contact, a habit he paradoxically eschewed during the pandemic. The crazy thing was, such was the monolithic ubiquity of the Times in New York that you’d write a story like that, and everyone would read it. You could make someone’s day by putting them in a piece. Or the opposite. When I found out that the congenitally exclusionary restaurateur Keith McNally had a top-secret reservation line for his boldface bistro, Balthazar, I published the number. That enraged him and made me feel like a nightlife Robin Hood.

Despite the paper’s unequivocally liberal bent, 20 years ago we were pre-woke, pre-#MeToo. No diversity directives were imposed on our section, which largely covered and (my goal) épatée’d the New York bourgeoisie. I wrote about Amish chic and $400-a-day cleaning ladies, lamented the rise of the G-rated bachelor party, and covered the pointless excess of the $1 million fish tank. I DJ’d at a Chanel store opening in Soho and became the paper’s first Burning Man correspondent.

My last piece in the Times was published a week before 9/11 would make the trend pieces that had been my trade for the past decade (Soup is the new coffee!) seem rather…beside the point. A piece on my fetish for Bic four-color pens and another on my annual addiction to the 1951 Alastair Sim version of A Christmas Carol were among my most popular. I was a devoted fan of the writer Bruce Jay Friedman, so I talked Trip into a profile of him whose paper-thin news peg was a reissue of Friedman’s novels and short stories. I don’t know how many readers were dying for that one, but it gave me a lifelong friend and mentor. On Valentine’s Day, my soon-to-be-wife Ilene and I wrote dueling screeds about “Women with Commitment-phobia” and “Men Whose Biological Clocks Are Ticking.” Off of that, I persuaded the section to give me my own column, called “Beta Male,” mostly because I hoped I could use it to sell a TV show. That never happened, but one of my rants, “Why Sane Men Love Crazy Women,” became the basis for a memoir I would leave the Times to write.

I was done telling other people’s stories. I wanted to tell my own. And I never looked back. Writing for television is a terrible feast-or-famine business. But my old colleagues who stayed in print had it worse. They watched budgets shrink or disappear altogether as magazines and newspapers shuttered right and left. Forget $5 a word. Journalists found themselves encouraged by the likes of Arianna Huffington to donate their services for free. One friend likened her profession to “working inside a rotting corpse.”

When I was at the Times, a digital display next to the elevators in the lobby advertised the company’s daily stock price, which vested employees obsessed over. It hit $48 when I left in 2000. By 2009, it had nose-dived to $4. It’s only now climbed back to its former high—on the back of a digital platform that would have been disdained in the days when its pious leaders deemed even TV too outré, much less the crass and lowly Internet.

After the paper moved to its current home, a sleek Renzo Piano tower on Eighth Avenue, I asked my old colleague Ginia Bellafante—who covered fashion in my day and now has a weekly column—for a tour of the mod new digs. The first depressing thing was how empty it was. “Most people work from home now,” Ginia told me. She came in only once a week, for appearances’ sake. Besides being empty, it was deathly quiet. And this was before the pandemic.

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When I applied to Columbia Journalism School in the mid-’80s, you had to come to New York, sit in a classroom with typewriters on the desks, and bang out a response to a New York Times editorial in something like two minutes. It was as much a typing test as a writing test. By the time I was accepted, a few months later, the typewriters were already gone, replaced by enormous clunky computers with five-inch floppy disks that were constantly deleting hours of hard work. Computers made newsrooms quieter, but they were still lively, cluttered hives of humanity at its best and worst. They taught me to write in the middle of chaos. No Hollywood deadline compares with an editor breathing down your neck to turn in your copy in five minutes or they’ll have to run a “house ad” where your story was supposed to be. Oh, and make it funny.

Working at the Times took me as far as I could go from that typewriter at Columbia. It also gave me the keys to the city. I went to any event, all the best restaurants, and had carte blanche to write about pretty much whatever I wanted. When I filed my story, I was done for the day. Those days are long gone. A mom on my kid’s old baseball team works for People. At every game, she was on her phone—endlessly posting, re-editing, updating. Whatever journalism has turned into now, one thing it doesn’t look like is fun.

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