On Friday, March 3, some local movers and shakers gathered at Maxim’s, the city’s art nouveau special-events venue, to celebrate the tenth anniversary of Stop Smiling. It’s a slick locally produced and internationally distributed lifestyle magazine whose declared mission is to recapture the freewheeling spirit of class acts like Esquire and Playboy in their glory days.

I didn’t go, but here’s what I heard. Hipsters in their party best sized up what other hipsters were wearing. Guests of honor Lois Weisberg and Rick Kogan rubbed shoulders with folks from Lumpen and Thrill Jockey. Nobody danced, save one guy who jumped around like a monkey when DJ Ben Fasman put on some reggae, but people ate the oil-cured olives and artisanal cheeses and got drunk on booze that didn’t run out before the party was over–the hallmark of successful party planning, if not a successful party. In his brief remarks, emcee Ira Glass congratulated the editors for sticking to their aesthetic vision. “It’s inspiring when people are making stuff that’s really about their own obsessions,” he said, “and not worrying about what anyone else thinks, or what every other magazine does.”

Glass is right: Stop Smiling has a lot to recommend it. Each issue, organized loosely around a single theme, aims for a timeless quality at odds with the “flavor-of-the-week” ethic of celebrity journalism. The editors idolize the giants of New Journalism’s golden age. Recent features have included selections from the papers of Terry Southern, reminiscences by friends and associates of the late Hunter S. Thompson, and, in the “boxing” issue, a lengthy, fascinating interview with Norman Mailer conducted by his son. “We’re not trying to sell anything,” says editor and publisher JC Gabel. “We’re not trying to be hard-nosed journalists and we’re not trying to be fluff. . . . We’re a lifestyle magazine technically, in the eyes of advertisers, but if anything we’re a lifestyle magazine that’s poking fun at the idea of what a lifestyle magazine is.”

Stop Smiling has come a long way from its origins as a zine Gabel produced in his Columbia College dorm room. About four years ago Gabel, now 30, hooked up with James Hughes, who’s the 26-year-old son of filmmaker John Hughes, and they decided to step things up a bit, enlisting the services of New York-based design team Trooper. Thanks to striking art direction and some distinctive original photography, the issues since have had a sophisticated, coffee-table-quality look. Stop Smiling now claims a circulation of 60,000.

Not long ago, Gabel brought in an advertising manager who’s helped pack the pages with glossy, four-color pitches for Absolut and Scion at the rate, at least officially, of $4,500 a page. They also brought in a private investor they decline to name, and last year they were able to move the enterprise out of Gabel’s Bucktown apartment and into a fixer-upper storefront on Milwaukee Avenue in Wicker Park. The rear of the space is full of iMacs, squeaky new Ikea fittings, and stacks and stacks of back issues. The airy front room is intended to function as an events space for parties and for public discussions with authors and other figures. Gabel’s currently talking to WBEZ about broadcasting them.

The anniversary party at Maxim’s doubled as a release party for issue 24, the “Chicago” issue–a celebration of all things homegrown. Its subjects are a collection of local fixtures: there are Q & A sessions with Glass, Weisberg, Studs Terkel, jazz DJ Dick Buckley, architect Dirk Lohan, and filmmaker Steve James. Writers tip their hats in a few paragraphs to institutions like Lookingglass and Jazz Record Mart. There’s a trio of vintage Mike Royko columns introduced by his son David, a reproduction of a mildly risque Shel Silverstein cartoon for Playboy, and a portfolio of Victor Skrebneski portraits of famous Chicagoans like Cardinal Joseph Bernardin and John Malkovich.

The magazine makes a habit of printing issues with multiple covers. This time around the cover subjects are Hugh Hefner, Vince Vaughn, and, in what the editors feel was a coup, Mayor Daley, who’s wearing a White Sox cap and wagging his finger at the camera. It’s not easy to score an audience with hizzoner–Gabel says it took several months of finagling–and when they sat down the parameters were predetermined and strict. So Gabel didn’t quiz the mayor about the hired truck scandal, or the water department heroin ring, or the Millennium Park budget debacle, or the smoking ban. He asked instead how that ticker-tape parade for the Sox got put together so fast.

Gabel and Hughes make it clear that they aren’t interested in going for the gotcha. “It’s not our job, really, to be busting him up for machine politics or corruption in his administration,” Gabel says. Plus, confrontation is exhausting. “Especially with the older people we talk to, we want to put the ball in their court. I think people need a little bit of a break from the constant attack of the media. We want to provide that a little more.”

The magazine lets subjects vet articles and request changes before they’re published. “Sometimes it’s such an accomplishment to just be able to be speaking to some of these people, that we know that, obviously, they’re going to be looking at the piece later,” says Hughes. “Where we’re at, it’s just better to be more symbiotic than adversarial. We’d never try to out someone on something that they’re hiding from. We’re not looking for scoops. If we’re going to spend this much time on something, then the people on the cover who gave us an awful lot of their time, then they’d better be happy with it too.”

That sound you just heard? Was it Hunter Thompson spinning in his grave? There’s a difference between lionizing bygone writers such as Thompson and carrying on their legacy of profane truth-telling. Those writers were often adversarial; they put the interests of their readers before the interests of their subjects.

Stop Smiling can be strangely toothless. For instance, as an example of the magazine’s alternative take on the celebrity profile, Gabel points out that not once during the interview with Vince Vaughn did the name of his girlfriend come up. Which proves that Stop Smiling isn’t US Weekly, but can’t have done much else but settle the editors more firmly into their subject’s good graces.

Gabel and Hughes say they simply write about things they love. They’re fans, and having a glossy magazine has given them more access to those things than fans usually get. If you’re editing a fanzine, that’s mission accomplished. But Stop Smiling isn’t a zine anymore–a point Gabel has repeatedly insisted upon. It wields all the power that comes with having 60,000 readers and more than a couple grand in advertising dollars. And to paraphrase Spider-Man, with a little bit of power comes at least a little bit of responsibility.

At this point you’re perhaps thinking it’s bad form to come down so hard on such a polite and pretty little magazine. But this just speaks to the mentality that’s part of Stop Smiling’s problem. The Second City is a city of boosters–led by Daley, our booster-in-chief-for-life–and Gabel and crew have drunk the Kool-Aid. Nelson Algren’s famous quote, “Loving Chicago is like loving a woman with a broken nose,” turns up not once but twice in the Chicago issue, but the Chicago celebrated therein has had a nose job. It’s a shiny metropolis flush with success and can-do spirit, ruled by the benevolent hand of a baseball-loving Bridgeport mug. It’s a city without corruption and without conflict, a city without poverty, segregation, failing public schools, or ugly condos. (It’s also a city without such odd, unofficial pleasures as old-man bars and chocolaty air and, for the most part, without black people or women.) In short, Stop Smiling’s Chicago is so polished and risk averse it might as well have been conjured by City Hall.

Boosterism may be good for tourism, but it isn’t the cure for second-city syndrome. A healthy skepticism is. It’s what fosters a vital, vibrant, dynamic cultural life, not to mention the thick skin needed to make it on the global stage. The best thing you can do for a subject, whether it’s a city or a celebrity, is to take it seriously, to assume it’s a grown-up and treat it as such.

The Stop Smiling guys could learn a little from their idols. One of the Royko columns excerpted in the Chicago issue is on the importance of keeping your subjects at arm’s length. “If I sit down for dinner with a president,” Royko wrote, “I feel like an ‘in-person.’ I am no longer some guy who grew up along Milwaukee Avenue. I am a VIP, big heat, or why else would a prez invite me to chow down at the White House? . . . So as much as I like politicians, I keep my distance. It’s the only way I can keep whatever scruffy integrity I have.”

Art accompanying story in printed newspaper (not available in this archive): photo/Andrea Bauer.