Invariably, the complaint about Chessmen is that they’re “boring.” But frankly, if you’re bored by these handsome, buttery things, it says more about you than it does about the cookie. And if it’s Milanos you prefer, consider that Milanos are basically everyone’s favorite Pepperidge Farm cookie. It’s like saying your favorite band is The Beatles.
A few months ago, a friend said to me, with disconcerting severity, “There’s something perverse about enjoying such a boring cookie.” I was moved to wonder: Is there something perverse about me? What kind of person am I, and how am I different from people who prefer, say, Veronas or Genevas?
It was then that I decided to sample every cookie in the Pepperidge Farm family and figure out what was what. I would try to understand what made each cookie special and seductive—and what it might mean to be drawn to one of them more than another.
My timing turned out to be perfect. Seventy-five years after a New England mother by the name of Margaret Rudkin started the company with a loaf of special bread baked for her allergic young son, Pepperidge Farm was getting ready to celebrate its Diamond White anniversary. It was also undergoing a transition that would see its longtime president, who has been with the company for more than 30 years, succeeded by a young new leader. And most thrilling of all, I learned that this month, Pepperidge Farm will be opening a $30 million Innovation Center at its headquarters in Norwalk, Conn., which will allow its team of cookie specialists to invent more new cookies each year than ever in its history.
By the time I found myself standing in a room full of metal machinery, surrounded by bakers in white aprons and staring at a tray of freshly baked cookie prototypes that I was not even allowed to photograph, it was clear that my task was no longer just a glorified taste test. What had begun as a narrow inquiry into my own peculiar inclinations had turned into an occasion to reflect on a company that is a pillar of the American pleasure industry—and to consider how we, as cookie-eaters and human beings, ought to feel about it as it marches into the superabundant future.
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One day this summer, I received a package from Pepperidge Farm the size of a laundry basket. I opened it immediately. Inside I found more than 30 varieties of cookies, including all the classics, as well as a bounty of Milano spin-offs—toffee and almond Milano Slices? Dark classic crème Milano Melts?—I’d never even seen before.
I was dying to dig in but forced myself not to indulge my gluttony. I’d need a notebook and a real chunk of time to do this right. I did, however, examine my haul—turning the bags over in my hands and reading the lyrical descriptions printed on each. I learned that Gingermen are an occasion to “take pleasure in the simplicity of a cookie well baked,” while the Raspberry Milanos channel the “baker’s soul” and implore the consumer to “embrace decadent cravings.” Several of the bags promised “velvety soft hearts.” The Shortbread boasted of its “dreamy, biscuit like-crisp.”
Setting the cookies aside for the time being, I placed a call to outgoing Pepperidge Farm president Pat Callaghan, who was preparing to retire just a few weeks later, after more than three decades in the post. Cookies have been part of the Pepperidge Farm arsenal since 1951, Callaghan told me, when founder Rudkin decided to expand her business beyond bread and try her hand at sweets. The initial results were not impressive—“pedestrian,” to use Callaghan’s word. Facing her failure, Rudkin decided she needed to look beyond her kitchen for inspiration.