What I learned about baked goods—and the human condition—from the Milano, the Verona, the Geneva …

“All of the cookies within our distinctive cookie range—Geneva, Milano, Chessmen, everything in a small white bag—are about ‘mom’s moment,’ ” he said. “The distinctive range is all about that delicate, special moment of reward and a little bit of escape—just a wonderful experience at the end of the day.”

More than two-thirds of the “distinctive” cookies are purchased by women, according to Konstanty. With Sausalitos, Nantuckets, and the rest of the chocolate chunk line—“a different kind of experience from an eating perspective”—it’s more like half.

I kept all of this in mind as I sat on my floor and ate my cookies. The idea that I was behaving in a womanly manner in cherishing the taut jelly center of the Verona, or that I was being somehow mom-like in feeling delighted by the tawny, tempura-like surface of the Brussels, made me self-conscious at first. To compensate, I tried the Tahoe, a crispy, tough number with white chocolate and macadamia nuts, and the Chesapeake, which is shot through with dark chocolate and pecans. Maybe there really was something a little more masculine about them, I thought, before reaching defiantly for a Pirouette and breathing through it like a straw, as one does.

All told, it took me about six hours to get through everything I’d been sent. By the time I was done, I had tried one of the forthcoming “soft dessert cookies,” three fruit cookies, all four entrants in the down-to-basics “simply scrumptious” line, five butter cookies, six chocolate-based “distinctive” cookies, eight types of nonstandard Milanos, and 10 varieties of chocolate chunk. Having done so, I felt an arguably unearned sense of accomplishment—as though I’d educated myself somehow and now knew more of the world than I used to.

In truth, all I’d done is confirm a few long-standing intuitions about the Pepperidge Farm brand. The first of these is that PF cookies are great because they manage to be refined without coming off as pretentious. This is not a trivial accomplishment. It’s hard to imagine a better example of middlebrow philistinism than an elaborately crafted cookie that’s been randomly named after a fancy European city—the kind of cookie that Nabokov’s Charlotte Haze would keep in her cupboard and nibble while listening to the vulgar ringing of her wind chimes. But something rescues Pepperidge Farm cookies from evoking such lowly associations. And having eaten them all, I think that thing is that … they’re cookies. By their very nature, they are guileless and eager to please, and insofar as they play at sophistication, they do so with jauntiness, and without desperation. The Montieri, for instance, is not trying to fool anyone with its fancy lattice patterning—it just wants you to think it’s pretty.  

I am not saying Pepperidge Farm cookies do not take themselves seriously. On the contrary—and this is the other intuition I ratified in the process of my research—I believe that the very best Pepperidge Farm cookies, above all my beloved Chessmen, require focus, patience, and maturity on the part of the person eating them in order to truly fulfill their potential. Unlike most other cookies—I’m thinking of Oreos and Chips Ahoy, but even Lu’s supposedly upmarket Petite Ecolier—they shine brighter under scrutiny. Just go ahead and put a Chessman, a Bordeaux, or a Gingerman in your mouth and start chewing. It might strike you as unremarkable at first. But soon the hard, crunchy cookie will turn into a pleasing goop that resembles melted ice cream or sweetened condensed milk. The flavor will make itself known gradually, growing more intense with time. The goop will get dense but you will be able to swish it around freely—an extraordinary feeling. In the end, it will feel like you are saying goodbye to something you’ve fought for. You will hesitate to swallow until you remember there are more in the bag—a fact that is easy enough to forget thanks to PF’s unique approach to packaging, with the cookies neatly divided into three vertically stacked paper cups.

Unfortunately, I cannot sincerely rhapsodize in this manner about any of the next generation cookies Pepperidge Farm sent to me. Putting aside the fact that I don’t quite understand how a Milano Slice is really a Milano—it would seem an open-faced Milano would be a contradiction in terms, seeing as the sandwich structure of the original is its defining feature—I’m afraid the new class, though bold and good and occasionally even thrilling, just didn’t pull me in like my old favorites do. I say this with some reluctance, well aware of the possibility that I’m just being a cranky “kids these days” reactionary—that I’m reacting to these new cookies the way my dad reacted when, as a teenager, I made him listen to ska punk in the car.  

The reality is that Pepperidge Farm has to keep up with the moment, or else risk turning into a nostalgia act, doomed to die out with the generation to which it has committed itself. But as the Innovation Center hums to life this fall, and the new models start coming faster than ever, possibly displacing some of the golden age cookies on grocery store shelves, I hope Pepperidge Farm realizes it must take care of the past as well as the future—that they must not confuse mere change for evolution.

This is especially important because there is such a thing as cookie extinction in the world of Pepperidge Farm. Flipping through the old black-and-white magazine ads collected in the Pepperidge Farm archives, I saw alluring, long-gone lines like “Little Fingers,” a chocolate brownie nut cookie, and “Distinctive Cappuccino,” a little coffee-flavored guy with chocolate praline filling, and I imagined a future in which my Chessmen looked as foreign to America’s cookie-eaters as these relics did to me.

That said, as I sit here on my bed with no fewer than three kings and horses swishing around sweetly in my mouth, I’m confident Pepperidge Farm will never stop making them, or even relegate them to the retirement home that is the “classics” sampler pack. And if one day it is determined that the line needs a shot in the arm, I suspect some genius in the Innovation Center will be able to come up with something. May I suggest dipping them in chocolate? “Chocolate Chessmen” has quite a nice ring to it, and they would be pretty good, I think.