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The idea of an ice cream sandwich is preposterous.
Not only cookies, not only ice cream, and not only ice cream accompanied by cookies, but a fused ice cream-and-cookie mass that you can eat three times as fast as if you were to tackle the components on their own.
And when you coat the whole thing in melted chocolate, then refreeze it to create a hard shell... well, it becomes a dessert so unbelievable that it could only come out of California.
It becomes an It's-It.
I spent most of my life thinking of It's-Its as the unicorn of the frozen dessert world.
They belonged to that far-off land where the type of produce that we on the East Coast think of as summer-exclusive is available year-round (tomatoes in December, you hear that!?) and eaten on porches and patios. Where people go surfing after work. Where celebrities walk the streets like you and me! Not real life. A year-round summer camp.
According to the official record, It's-Its were conceived in San Francisco in 1928, when George Whitney pressed vanilla ice cream between two freshly-baked oatmeal cookies, dipped the fat saucer in dark chocolate, and pronounced "It's it!" And so was born an iconic Bay Area dessert, served exclusively at the Playland-by-the-Sea amusement park for four decades.
I was lucky enough to catch my first It's-It at Creative Director Kristen Miglore's wedding, where she served them alongside cobbler. (And in case you don't click through the Instagram comments to read guests' enthusiasm, know that someone wrote, "This is gonna be the best wedding ever. That's real strong dessert game right there. ITS IT!!" And they were right.)
Keeping in mind that it might be a long time—years, even—before I was back on the West Coast with an It's-It in hand, I forced myself to choose my flavor carefully, to eat it slowly. (Also motivated by preserving my fancy attire.)
But it turns out that It's-Its have now stretched far beyond the Bay Area. I could have them shipped from the website, but they're also available at multiple grocery stores between the Food52 offices and my apartment, and on FreshDirect, too. I could have one—heck, I could have two!—tonight.
The unicorns roam close to home. (And in Maine, too, where the Harbor Bar—in which chocolate chip cookies flank by ice cream and are coated in chocolate—is a close cousin.)
But, for the sake of my wallet and my belief in
unicorns awe-inspiring desserts, I have taken a vow to do some work for my It's-Its, be it buying a cross-country plane ticket or making them myself.
Because the biggest shame would be for a frozen dessert so spectacular to become mundane. It's-Its just taste better when they're coated in mysticism (chocolate, too).
Here's what you'll need:
- A batch of Merrill's Crispy Crunchy Oatmeal Cookies: If you want full-sized (that is, gargantuan) It's-Its, make big cookies—I made about 18 cookies, each with about 2 tablespoons of dough; stick the baked cookies in the freezer until they're super-cold before proceeding.
- Great-quality vanilla ice cream, be it homemade or store-bought (I'd recommend store-bought: It's more likely to be a nice texture right off the bat and it will keep for longer in the freezer); you'll also have an easier time smooshing together the cookies if you let it soften a little at room temperature.
- 24 ounces of dark chocolate + 3 tablespoons of canola oil (or, make magic shell using coconut oil)
Once all components are ready—and at the right temperature—assembly is easy:
- Ready parchment-lined baking sheets.
- Flip half your cookies over and plop on a generous amount of slightly-softened vanilla ice cream. (My eyeballed amount was 3 parts ice cream to 1 part cookie, per Cristina Sciarra's suggestion).
- Smush the bare cookies on top. Use your hands and/or a spoon to smooth the sides. As I said before, easier with slightly soft ice cream.
- Rush the cookie sandwiches to the freezer and leave them be until thoroughly chilled, with re-hardened ice cream—at least 3 or 4 hours, to be safe!
- When the cookies are ice-cold, melt the chocolate and canola oil (or coconut oil) in a saucepan over the lowest heat, stirring constantly. Transfer the mixture to a bowl deep enough to swallow most of a sandwich and allow it to reach room temperature. (You can also let it cool off in the pan, but it will lose heat faster in a non-heated vessel.)
- Working with one sandwich at a time, dunk the entire thing in the melted chocolate, using a slotted spoon to flip it over so that all sides are coated. Pick the sandwich up with the spoon, allow some excess chocolate to drip off, and then return to the parchment-lined baking sheet.
- Place the chocolate-coated sandwiches back into the freezer and let the chocolate harden. (I'd say, an hour; some would say as little as 15 minutes—the risk is yours.)
Do you have a dessert you know you could have anytime you want but that you save for special occasions? Name your "It's-It" in the comments below.