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My Two Decades with The Improper Bostonian

Improper Bostonian covers through the years. From left, 2017, 2011, 2007, and one from the inaugural year, 1992.

Improper Bostonian covers through the years. From left, 2017, 2011, 2007, and one from the inaugural year, 1992.

Twenty-seventeen was a milestone in my relationship with The Improper Bostonian magazine, marking 20 years since I first reached out and offered to redesign the publication. Rounding out my year at the Boston Globe, bored out of my mind by the glacial pace at the lumbering daily, I hungered for a fresh challenge. I penned a letter to then-owner and publisher Mark Semonian stating that while I liked his scrappy little tabloid—an unbound, free, newsprint bi-weekly—I could help make it a player. Indeed, the media scene was somnolent for a college town, only The Phoenix and The Harvard Crimson serving as alternatives to mainstream papers, so there was room to make some noise. The Improper’s moniker hooked me, a brilliant inversion of the city’s historical legacy of proper blueblood Brahmins. The name declared the pub’s intentions to afflict the comfortable, topple fusty conventions, and tweak noses all over town. In its existing form, it was, however, more likely to be ignored than feared. 

I contracted with The Improper for a six-month project to redesign and reposition the pub and then art direct it for half a year to get it rolling. (As a newbie to Boston my ulterior motive was to place myself on the radar of the more established—and establishment—Boston magazine. At the conclusion of the Improper project, I became art director at Boston mag, where I remained for four years.) My first move was to drop the unbound newsprint tabloid in favor of a saddle-stitched, over-sized magazine format with a glossy cover and upgraded interior stock. Second, I ordered all advertising redesigned in-house, a seismic event initially rebuffed by the sales staff, which was headed by Mark’s sister Wendy, but Mark had my back and supported the move. It was necessary because the crude, homely ads as they were would defile the new editorial design, rendering the entire exercise moot. Sort of like wearing dirty, worn sneakers with a brand new tux. Up to that point, all ads were slapped together by an incompetent staff designer or supplied by advertisers, typically local bars, clubs, and restaurants. There was no hope of attracting higher-caliber advertisers without a minimum approval standard in place, a cultural shift at the five-year-old publication that set the tone for its subsequent growth.

The editor-in-chief was veteran journalist Nancy Gaines, a hard-bitten alum of the rough-and-tumble newspaper world, having won her spurs at The New York Times, Boston Globe, the Herald, and the Boston Phoenix. While she and Mark had different missions in mind for the Improper—Mark aspired to achieve the influence of a Vanity Fair while Nancy enjoyed menacing the establishment—the days of being truly improper withered in the face of lawsuits over two stories whose protagonists were displeased with their unfavorable coverage. The Semonian family, who backed the venture, lost their appetite for adventure and the magazine morphed into an inconspicuous compendium of light fare about restaurants, entertainment, and shopping. It also pivoted to an embrace of advertising-friendly themed issues, like Bachelor/Bachelorette, Fashion, Best Bartenders, and the jackpot Boston’s Best annual awards. The new editorial direction insulated the Improper from controversies and set it on a winning trajectory with national advertisers buying into fat, perfect-bound issues on full glossy stock. In the midst of that ascent, I was asked to briefly cover for the art director who had just resigned around Christmas 2004. That lead to my second redesign, followed by a third redesign a few years later, with on-going cover art direction, photography, and design. By the time of my return, the magazine had been regularly featuring a mix of local and Hollywood celebrities and athletes with Boston connections, a successful formula that continues to this day. Marquis names from Matt Damon, John Krasinski, Rachel Ray, and Shaq to Conan O’Brien, Bill Belichick, Mindy Kaling, and Katharine McPhee have graced Improper covers elevating the magazine to the presence and stature of a national magazine. It’s been a privilege to have been part of it for so long. And to have worked with a variety of talented editors, producers, art directors and, of course, Wendy Semonian, the visionary publisher who assumed leadership from her brother so many years ago.