The It’s-It company began selling scoops of vanilla ice cream sandwiched between old-fashioned oatmeal cookies cloaked in chocolate at San Francisco’s Playland at the Beach in 1928. By the time I moved to the area in 1978, the It’s –It was a well-established local phenomenon. I’ve filled my version of the novelty with a not-overly-sweet vanilla frozen custard.
Don’t be put off by the recipe’s many steps: Each is reasonably quick and easy, and one bite will convince you it was all worthwhile. I half-dip the sandwiches for a pretty finish. If you wish to fully dip them, double the Chocolate Shell recipe.
Whisk the yolks with 1 tablespoon of the sugar in a medium bowl until smooth and slightly thickened. Set aside.
Whisk 1/2 cup (120 ml) of the milk with the syrup, tapioca, salt, and the remaining 1/3 cup (67 g) sugar in a medium saucepan until no lumps remain. Stir in the cream and the remaining 1 cup (340 ml) milk. Use a paring knife to scrape in the seeds from the vanilla bean; toss in the pod. Heat the mixture over medium-high heat, stirring with a heatproof spatula, until it begins to steam and slightly bubble at the edges.
Ladle 1 cup (240 ml) of the hot mixture into the yolks in a stream as you whisk the mixture to prevent the yolks from scrambling. Whisk the mixture back into the saucepan and cook at a slow simmer, stirring with a spatula, until the mixture thickens enough to thickly coat a spoon, 1 to 2 minutes longer.
Strain the mixture through a fine-mesh strainer into a metal bowl. (Rinse and save the pod for another use, or discard.) Stir in the vanilla extract.
Preheat the oven to 350°F (175°C) with racks in the upper and lower thirds of the oven. Line two baking sheets with parchment paper or silicone baking mats. Whisk together the flour, baking soda, baking powder, and salt in a small bowl.
Put the butter and brown sugar in a mixing bowl and use a wooden spoon or a handheld electric mixer to mix until they are creamy. Add the egg and vanilla and mix until smooth. Stir in the flour mixture just until everything is well combined, then stir in the oats and raisins, if using.
Spoon or scoop the batter in tablespoons onto the prepared baking sheets, spacing them evenly to make 24 cookies. Press the cookies with lightly dampened fingers to flatten them slightly – they will spread further as they bake. Bake until the cookies are light golden around the edges, 8 to 10 minutes, rotating the pans top to bottom and front to back halfway through baking.
Let the cookies cool on the pan for 5 minutes, then transfer them directly to a wire rack to cool completely, sliding a spatula under them if they do not release easily.
4. Freeze until firm, at least 2 hours, before dipping. Dip the sandwiches to coat them halfway in chocolate following the instructions below.
Makes enough to half-dip about 12 sandwiches or fully coat 6 to 8 sandwiches.
This chocolate coating could not be easier. A bit of oil keeps the chocolate smooth for dipping, then magically helps it to harden to a brittle coating in only a few minutes in the freezer. The elegant chocolate layer shatters beautifully when you bite into the sandwich, melting smoothly on the tongue.
I prefer an extra-bittersweet chocolate for this – 64 to 72 percent cacao – but choose whatever chocolate you like, from milk to dark. For a white chocolate shell, increase the oil to 1/4 cup (60 ml), and choose a good-quality white chocolate, such as El Rey, Ghirardelli, or Guittard (not chips).
The sandwiches should be firmly frozen before dipping. To decorate the sandwiches, press chopped and toasted nuts coconut, sprinkles, or other decorations onto the dipped sandwiches before the chocolate firms. Any remaining Chocolate Shell can be melted and served over ice cream, or can be stirred into ice cream as it spins for a stracciatella (chocolate chip) effect.
Melt the chocolate with the oil in a double boiler or bowl placed over, but not touching, about an inch (2-1/2 cm) of simmering water in a saucepan. Alternatively, melt the chocolate with the oil in the microwave until you can stir it smooth. You do not need to get the chocolate very hot – just warm enough to melt when you stir it. Set aside until the chocolate is just barely warm and still smooth and fluid.
Dunk a sandwich into the chocolate to coat half or all of the sandwich, using a small offset spatula as an aid to paint on the chocolate and scrape off any excess. Transfer the sandwich to the baking sheet in the freezer. Repeat to coat the remaining sandwiches. Freeze until the chocolate sets, about 15 minutes, before individually wrapping the sandwiches or layering them between sheets of parchment or waxed paper in an airtight container.
Substitute oatmeal cookies and vanilla ice cream.
Immediately after dipping each sandwich, dunk the soft chocolate into a bowl of chopped toasted nuts.