It's All About Joel

Time magazine's most irreverent writer has quizzed a rock legend on his golf handicap, eaten fried chicken with a porn star and become Robert Goulet's pen pal. But that's nothing compared to his favorite subject: himself.

by Jesse Oxfeld

Photography by Chris Callis

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AS IT TURNS OUT, Joel Stein is a dork.

Of course, an inherent dorkiness is part of the shtick of his Time magazine column. But if you read the columns closely, there’s a strong suggestion that while the “Joel Stein” who stars in the weekly column is a dork, the Joel Stein who writes it—the one who, at age 30, has become one of the best-known names in the nation’s oldest, richest and top-selling newsmagazine—is not. “Joel Stein,” as portrayed in the columns, is desperate, awkward, porn-loving and obnoxious; Joel Stein, however, is worldly, knowledgeable, chummy with celebrities and in possession of an enormous expense account.

And, I suppose, the conceit is true. Stein the author is worldly and knowledgeable and all that.

But he’s also a dork.

When I called Stein, ’93, MA ’94, and said that STANFORD wanted to profile him, he made every effort to play the big shot. First we tried to make a lunch plan. “Would the Friars Club be good?” he asked solicitously. Um, yes, that would be fine. When we couldn’t find a good day, we decided to have breakfast instead. “Let’s go to the Rainbow Room,” he said. “I’m a member.” Of course. And so I found myself on a beautiful summer morning sitting on the 65th floor of Rockefeller Center, looking through wraparound picture windows at most of Manhattan, with the Empire State Building just in front of me, Central Park behind, and Vernon Jordan, I’m pretty sure, at the table to my right. Then and there, I believed: Stein is a player.

Until he showed up. Joel Stein has definite big-shot potential—handsome, tall and slim, with fashionable short hair (freshly gelled for breakfast) and hip little glasses—but the potential was pretty much squandered. He was a little late, which was fine, but way, way too apologetic about it. Also, he didn’t so much match. (I don’t quite know what pants I’d wear with a yellowish, linen-y sport coat, but I’m sure they wouldn’t be khaki.) We started talking, and he was more interested in asking about my life than in telling me about his, a decidedly non-big-shot behavior. When we walked to the buffet, his lox-and-onions omelet was ready; I was impressed. Then he confessed he doesn’t actually like the omelet, he just likes having a “regular.” He’s big-shot enough that the hostess knew him as Mr. Stein but awkward enough that neither she nor I could decipher the theoretically flirty joke he made to her. Together, this all proved one thing: try though he might to be cool, Stein is still just a dork.

WHICH IS FINE. Because, for him, dorkiness is working out rather nicely.

Stein started at Time in the summer of 1997, writing cheeky snippets for the magazine’s opening Notebook section. He also contributed some longer articles, one of which was the seminal piece, he says, in introducing his self-focused tone to the straitlaced newsweekly. When President Clinton traveled to Stanford to drop off his daughter for her freshman year, Time sent along Stein rather than its usual White House correspondent. The story Stein filed, titled “Don’t Look, It’s Chelsea,” began not with an anecdote set aboard Air Force One nor with some paternal musing from the First Father. Instead, Stein talked about himself.

“It was embarrassing enough when my parents, crying, holding baby pictures and stuffing a flowery note into my carry-on bag, dropped me off at Newark Airport eight years ago for my freshman year at Stanford,” he wrote. “But Chelsea Clinton’s parents showed up at her Stanford dorm last Friday night not only mushy but also in a motorcade flanked by security guards and nearly 250 of their closest journalists. I would have died.”

That opening, Stein recalls, “seemed really inappropriate in this case, because it had nothing to do with Chelsea Clinton.” He had a straightforward first paragraph ready to go; he was waiting for editors in New York to complain. They didn’t. “They ran it,” he says, “which totally confused me.” Stein’s self-obsession, now so familiar to readers of his column, had entered the Time & Life Building.

(A disclosure: the Clinton piece, which opened with Stein discussing Stein, ended with him discussing me, then a Stanford senior and Daily columnist who was trying, pathetically, to make the most of the national media’s presence on campus. I was thrilled to get into Time, which I suppose biases me toward Stein, but I was also both misquoted and called “husky,” which could just as well bias me against him.)

Not only did Time’s editors run that bit of Steinian self-reference, they became enthralled with it. “I think he’s got the quirkiest sense of humor I see today,” says Walter Isaacson, the chairman and CEO of CNN News Group who, as managing editor of Time until the end of 2000, hired Stein and championed his career. “Joel’s honed that self-effacing self-indulgence to a great art form.” Soon it metastasized throughout the magazine. By the end of 1997, Stein had created his “Q+A” feature, in which he asks impertinent questions of movie stars and other notables, and in December 1998, he landed his marquee column.

In a magazine whose regular essayists include such deep thinkers as Charles Krauthammer, Margaret Carlson and Roger Rosenblatt, Stein’s column is decidedly lightweight. It’s about 500 words, recently moved from the Notebook section to the back of the magazine, where it resides alongside jokey quizzes about current events (co-penned by Stein) and gossipy celebrity tidbits.

At first Stein shared the humor-columnist space with Calvin Trillin, but eventually he took it over exclusively. “Alternating with him was the best thing for my career,” Stein says. “It’s like being serialized with Faulkner every other week.” And even though Stein edged him out of the magazine, Trillin is polite on the subject of his successor. “Oddly enough, I don’t qualify as a source on Joel Stein,” he demurred when I e-mailed to inquire about the younger humorist. But, he added, “I can say that I’m beholden to him.” Turns out that in a New York Times profile of Stein, the writer referred to Trillin as a “noted belletrist.” “Nobody had ever called me a belletrist before,” says Trillin. “In fact, I had to look it up.” (It means a writer of belles lettres—“light, entertaining and often sophisticated literature,” according to Webster’s.)

No one would call Stein’s commentary sophisticated. He’s veered, rather, in a new, what-the-hell-is-this-doing-in-Time-of-all-places direction. He has detailed his thoughts about body hair (both the copious supply attached to his lower half and that which might sprout from a potential lover). He wrote of bringing a porn star to Yale, where they visited a student group devoted to watching adult films while eating fried chicken. Another column analyzed his distaste for dogs, explaining that “I just can’t imagine sharing my apartment with some dirty, dependent animal willing to trade unconditional love for canned food that, to be honest, I find a little salty.” And once, in a column that did not much endear him to the University’s Office of Development, he explained why he does not donate to his alma mater: “Stanford already got a whole wad of Stein money. Outside of organized crime, it’s not traditional to charge someone for a service and then ask for more later.”

In his “Q+A” feature, he’s been hung up on by such diverse luminaries as Sharon Stone, Sandra Bernhard and Buddy Hackett. He asked the rapper Sisqo whether he was named “after the Internet router company or the food-service corporation,” Don Rickles if he “use[s] insult humor during sex,” Meat Loaf about his golf handicap and Esther Williams “if there was a guy in Hollywood [she] didn’t sleep with.” Joy Behar, Melissa Etheridge and (most extensively) Debbie Reynolds have—in jest, one assumes—raised questions about his sexuality.

This is all part of his dorky-but-cool thing. He’s big enough to get these people on the phone, and he’s goofy enough to ask them such questions. “My whole goal is to use Time magazine to make important people do stupid things,” he explains in his office one afternoon. It’s a comfortable warren, big enough for both a desk and a sofa. The walls are decorated with celebrity-drawn hand turkeys he’s collected over the past few years for Thanksgiving issues of Time: important people, stupid things. This time he’s looking very New York hip—dark jeans and a black T-shirt—but there’s something endearingly juvenile about his inability to sit still in his chair. In fact, contrary to his in-your-face magazine persona, Stein is a generally endearing kind of guy. He admits he watches much less porn than his column would suggest, reports he’s happily engaged to be married, and claims to live a pretty low-key life: he and his fiancée, Cassandra Barry, share a tiny studio in a swank apartment complex, and their typical Saturday night involves cooking and video rentals. He’s chatty, and—playing against columnist type—actually listens to what the other person is saying. At breakfast, and in his office, he worries repeatedly that I won’t have enough material to fill this piece.

OF COURSE THERE'S ENOUGH MATERIAL, because Stein seems to be everywhere. He’s a bona fide celebrity, at least in the New York media world. “Joel makes dorkiness cool,” says James Kelly, Time’s current managing editor. “I’ve been at various events with him where I feel like I’m with a rock star. I mean, people really want to seek out and meet Joel Stein.” Early last year, New York Times magazine-beat reporter Alex Kuczynski—herself a bit of a media celebrity, and certainly capable of bestowing celeb-hood—gave Stein a gauzy front-page profile in the paper’s business section. Folio:, a magazine-business trade publication, named him one of its “Thirty Under 30.” Brill’s Content put him on its annual “Influence List” for 2000 (more disclosure: I was that project’s lead writer). Stein also turned up in Vanity Fair last year as the magazine’s anonymous “Calendar Boy,” and when W did a fashion spread of dudded-up journalists, he appeared in a Tommy Hilfiger suit. Stein’s celebrity—what Isaacson calls his “cult following”—is tough to explain, even for a visible newsmagazine writer. Newsweek’s Jonathan Alter, for example, rarely appears in women’s magazine fashion spreads.

Gabriel Snyder, media columnist for the New York Observer, argues that Stein’s fame stems as much from the identity of his mentor as from his literary or comedic talent. “One of the things that’s definitely helped Joel’s status is that it’s widely known he was a personal favorite of Walter Isaacson’s,” Snyder says, “and Walter Isaacson being the kind of guy he is in this town, his favorites become other people’s favorites.”

Still, Stein’s not well-liked just because he’s well-connected. He invited me to come by his office one day to read his hate mail; we spent an hour or so digging through a file drawer full of all the correspondence he’s received, and we discovered a shockingly low level of whither-Time missives. Sure, there’s the occasional “you make an idiot look like a rocket scientist” (from a Los Angeles reader, about his column on the Commando Chicks, a subgroup of People for the Ethical Treatment of Animals), the indignant “how arrogant you are to belittle ‘unconditional love’” (hand-scrawled, regarding the anti-canine piece) and the crushing “I never expected this from you” (arriving from New Jersey, complaining about Stein’s treatment of shock jocks Opie and Anthony). But those are the exceptions. Most of Stein’s mail isn’t just positive; it’s adulatory. As I sifted through the drawer, I saw a good number of buddy-buddy letters from guys telling him he’s funny and seems cool, and a surprising number of letters from women telling him he’s brilliant and they love him and could they maybe meet. (More than a few included measurements.) There were several letters from famous people (including dozens from Robert Goulet, who’s somehow become Stein’s pen pal), commenting on things he had written. Teenage girls wrote to request autographs and teenage boys sought internships. With all these people—and especially with the girls, judging from the mail—it’s simple: Stein just connects. Indeed, Barry, who seems a bit flummoxed when reporters call asking about her future husband, says that’s why she doesn’t mind and in fact likes showing up in Stein’s columns. “He tends to get a lot of fan mail from the chicks,” she says, “so him reminding his female readers that he’s got a girlfriend—or fiancée—is nothing but a good thing, right?”

It certainly is, because these fans may soon be seeing a lot more of Stein. He conducts celebrity interviews for HBO, and he’s creating a cartoon alter ego who will do the same for VH1 (from the theme song, it’s apparent that art imitates life: “Joel likes to ask questions that’ll make ’em squirm/Sometimes he gets punched out/Joel never learns”). The real Joel Stein also has chatted with Isaacson about possible appearances on CNN.

A REGULAR GIG in a national magazine, doing exactly what you’ve dreamed of. Multiple television networks knocking on your door. A fiancée who likes it when you make fun of her in public. Outside of the movies, things don’t usually end up this way. Especially for English majors.

Stein left Stanford with a bachelor’s, a master’s and an armload of Stanford Daily columns. This is not generally how Cardinal grads go forth to make their fortunes. In his three years of Daily opining, Stein honed the style that he continues to deploy at Time. He was funny, he was savvy, he was loaded with pop-culture references and he was self-deprecating. He was also occasionally touching, writing about the loneliness that can plague freshmen, seniors’ worries about the future, and his breakup with his girlfriend. (“I think the worst of it was how kind she still is to me and how much she still cares,” he wrote. “Or maybe the worst of it is knowing that’s not enough.”)

When Stein graduated, he hoped to write for either television or magazines. He had no experience with the former and very little with the latter. Somehow he got himself a job writing for Martha Stewart’s then-forthcoming television show, a job for which, Stein acknowledges, “I was in no way qualified.”

He then moved on to several freelance research and fact-checking jobs, working for Readers Digest Books,TV Guide and, reuniting with the Goddess of Homemaking, Martha Stewart Living. In 1995, when Time Out New York was launching, Stein became the listings and entertainment magazine’s sports editor.

“When he got to me, the only clips he had were his Stanford newspaper column, but it was one of those things where his voice ran clear through his [cover] letter,” says Cyndi Stivers, Time Out’s editor. “I knew he was going to be a biggie.”

At Time Out, Stein wrote not only sports coverage and the magazine’s typical hipster-service features—on things like the best places in New York for inexpensive desserts—but also a variety of bigger, sometimes more serious pieces. “His dirty little secret is that he’s very well read,” Stivers says, citing an article he wrote for the books section about how to celebrate Bloomsday, which commemorates James Joyce’s Ulysses. And although Stein did a column for Time Out—a forerunner, more or less, to the Time column—he even wrote about people other than himself. “He did a profile that was pretty heavily reported on Howard Stern,” Stivers says. “He complained a lot—he was like, ‘You mean I have to call 50 people?’—but he did it, and he did a really good job.” Stivers also remembers the cool-but-dorky routine. “I mean, he’s always been perfectly good-looking and incredibly charming, but I remember our first managing editor teasing him and saying, ‘Joel, flat-front pants. Remember, flat-front pants.’”

Even while de-pleating his wardrobe, Stein kept applying for jobs at Time. (Several rejection letters now hang on his office wall.) After two years at Time Out, and several freelance articles for a Time-offshoot publication, he was finally hired.

“I didn’t think it would work out quite the way it worked out,” says Kelly, who was then deputy managing editor and formally offered Stein the job. He and Isaacson thought they were hiring a clever guy who would do general society and culture writing, with a healthy dose of sports. And, indeed, Stein has written cover stories on the dot-com lifestyle, America’s fascination with low-carb diets, and Venus and Serena Williams. But what Kelly calls Stein’s “obviously very funny prose”—“He makes me laugh out loud,” Isaacson says—convinced the editors to begin alternating him with Trillin, who had been writing the humor column. “So we, uh, we created the monster,” Kelly says with a laugh.

But, of course, he’s not a monster. “Folks who only read one column, or folks who fixate on this or that one trait that Joel depicts himself as having—primarily his taste for pornography, I guess—I think miss the whole comic persona of Joel,” says Kelly. “There’s no one he pokes more fun at than himself. The biggest surprise to people who only know Joel through his columns is that he is, in person, the gentlest, most self-effacing person you can imagine.”

In fact, it’s possible that all the big-shot trappings, all the airs of importance and the in-print indiscretions, are ways to cover up that inner nice guy. Certainly his mother, Roz Burd-Leszczuk, about whom he’s written less than kindly on more than one occasion, thinks he’s the most darling little boy. “Joel’s a wonderful son,” she says, “sensitive and very sweet.” But she also admits they have an arrangement: “He doesn’t write about me without permission. We made that deal back in high school.” Isaacson believes the cool-dork shtick serves a purpose: “He captures the fact that all of us, deep inside, know we’re dorks trying to hide it.”

And I briefly saw Stein stop trying to hide it. Near the end of our Rainbow Room conversation, long after Vernon Jordan had left, I’d asked him what comes next. He’d just gotten engaged (as the world would read in Time the next week), it was a brilliantly sunny day and he was looking out at the Empire State Building. “If my career kind of fell apart right now,” he said from this perch, “I’d feel like I got to do what I wanted to do, and I’d be happy.” Then he became knowing and smart-alecky again. “Now you’ve got your kicker,” he said. Indeed.

Jesse Oxfeld, '98, is a writer and editor for Brill's Content and Inside. com. He lives in New York City.

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