Which Common Grocery Store Cookie Brand is Best, Tates or Milanos?

Let's be clear, both brands are delicious. But only one can be the best.

Every day when I pick up my kids from aftercare, they emerge from their activities — archaeology and tiny science, respectively — chirping for special treats. This really gets my goat. “Look,” I say, “if you have a special treat every day, it stops being special.” They are immune to this logic, but I hold fast. I don’t always show up with cookies, but when I do show up with cookies, I want to make sure they are the best chocolate chip cookies available at the grocery store. I normally go with either Tate’s Chocolate Chip Cookies and Pepperidge Farm’s Chocolate Milanos. Why? Because they are far and away the best of the common cookie brands. They’ve got texture and taste and really solid packaging.

I choose them both because my kids like them and because I like them. There has never been a situation where uneaten cookies were wasted. The cookies get eaten.

Origin Story: Milanos were first invented in 1957, as part of Pepperidge Farm’s “European” line of cookies. Already extent was a cookie called the Naples, a now-discontinued open face chocolate cookie. When the Naples was shipped, especially into the South, it often melted so Pepperidge Farms invented the Milano, sandwiching the thing layer of chocolate with two oblong layers of shortbread. Since then, the Milano has proliferated even as the “European” line grew to include Brussels and Bordeaux.

Tates started off years and years ago as a child’s interpretation of that vaunted recipe found on the back of Nestlé chocolate chip. The founder of Tate’s Bakeshop, the formal name of the enterprise, is a woman named Kathleen King, who began selling cookies at her family’s farm-stand in Southampton, NY. Her odyssey to creating the best cookie is long and chronicled here. But one aspect of particular relevance is the cookie company itself was once called Kathleen’s Bake Shop but, after a business dispute in 2000, she lost the rights to the name. The case went all the way to the State Supreme Court — Weber v. King — and into the tabloids. King lost the case but her cookies were reborn — Tate is the nickname of her father — and in 2013, sold her share of Tate’s Bake Shop to a private equity fund called Riverside for $100 million.

Basically these origin stories are both iterations of evolution. One by virtue of success (Pepperidge Farms was expanding so rapidly they needed to innovate to keep up with demand in new climes) and the other by failure (Kathleen overcame human iniquity, starting from scratch again and bringing fame to her father’s name). Both are good stories but Tate’s edges a win.

Origin Story: Tate’s

Method of Chocolate Delivery: The chocolate of a chocolate Milano is a discreet layer and the eating of a chocolate Milano is the same pleasure as having folded laundry. Everything is in its right place. What with the crumb of the shortbread and the yielding substrata of chocolate, the chocolate Milano offers a vision of well-ordered diversity.

Tates are chocolate chip cookies and therefore rely on the chips being held equally distributed in suspension of the dough.The unexpected burst of chocolate chips in one’s mouth. The experience is left more to chance than the assuring uniformity of a Milano. One never knows from what angle and how a chunk of chocolate will hit you.

This is a matter of personal predilection, whether one prefers one’s chocolate to come as a surprise or as a confirmation. In his book Le Plaisir du Texte, Roland Barthes frames this as the difference between jouissance and plaisir, that is unexpected bliss or comforting pleasure. Though I am a bliss man in other aspects of my life, when it comes to cookies — which are perhaps by definition comfort food — I prefer to know exactly what each bite will hold.

Method of Chocolate Delivery: Milano

Cookie Taste and Texture: Thin and buttery, Tate’s are distinguished by their pleasing crunchiness. They do not yield and are not chewy. They are a sudden pleasure, a cracking delight. Tate’s are three- to four-bite cookies better halved by hand then quartered by mouth. Each bite is a miniature symphonic movement from the staccato attack of the opening bars to the lush legato of the last saliva-moistured crumbs.

Milano’s, by contrast, are made of a close-textured shortbread. The crunch of a Milano is less uniform than that of a Tate for it contains not just two layers of shortbread but the softness of the layer of chocolate. Tate’s crack; Milano’s crumble. And isn’t crumble exactly what a cookie is meant to do? On the other hand, a Milano is best devoured in only two bites, even by tiny mouths. And that becomes important when one is evaluating two cookies of such breathtaking wonder. The real question is this: Is the somewhat incremental superiority of the Milano taste and texture enough to hold a lead over an extra bite of Tate’s? Greatness is, after all, measured not by greatness per bite but greatness in toto. With that in mind it is with a heavy yet hungry heart, that I deliver unto Tate’s this category and, therefore, victory as well .

Cookie Taste and Texture: Tate’s

And the winner is: Tate’s

Though technically Tate’s Chocolate Chip cookies got the nod, the contest is a bit like Hagler v. Hearns. That is, both are champions, both are winners.