Why It Works
- The chocolate filling is made with a cooked flour-milk mixture, which results in a very fluffy filling that's sturdier than whipped cream and comes together without the use of eggs or powdered sugar.
- Adding vegetable oil to the batter makes for especially moist chocolate cakes.
I think I was in the second grade when I learned about whoopie pies. Every week we had a "craft day" where one of the moms volunteered to come in and work with the class to make a hands-on project. Thankfully my mom was too busy working her day job to worry about this sort of thing, so I was spared parental embarrassment and she was saved from stressing about what to demonstrate to the kids. I do remember learning some cool things though. I definitely brought home a paperclip necklace and have a vague memory of poking myself with wires to make some hippie burlap flower. I glued together a puffy red felt heart pillow which I soaked in perfume and gave to my grandmother.
Above all, I remember whoopie pie day. I remember the moist chocolate cakes filled with cream (they looked like a hamburger but were dessert—genius.) It made some lucky kid's mom a total hit with the class. These cakes mostly stuck in my mind because of their questionable name. Why was it called a whoopie pie? Was it meant to resemble that thing that you sat on to make a fart sound? It did look like a squishy cushion. But then again, there was also that song "feel like makin' whoopee", that I'd heard, and which I could only presume had something to do with sex—though I wasn't exactly sure how that related to cake. I was seven, I was confused, and it took many years before I could say "whoopie pie" without giggling.
Be it the goofy name or the fact that it's a handheld treat which, like cupcakes, lends itself to limitless variations, whoopie pies are still a hot product. But instead of trying to woo you by adding another far out flavor combination to the list, I chose to keep my recipe classic with a chocolate-on-chocolate version. The cake-y cookie is based on a recipe that I made every week at my bakery, simple and straightforward. For the cream, I've never filled my whoopie pies with either whipped cream or a sugary, quick butter frosting. I always make the one that reminds me of my very first: a cooked cream filling made from heating milk and flour until thick, then whipping it up with sugar and vegetable shortening until it reaches ridiculously light and fluffy heights.
Even though I'm a firm believer in the original version from my memories, I respect that vegetable shortening in a cream filling is not for everyone. So as well as making the filling chocolaty with cocoa and melted chocolate, I swapped out most (not all!) of the shortening for butter. The resulting cream is a little more vulnerable to melting sans shortening, but I won't complain one bit about the buttery flavor.
For the Cake:
2 cups (10 ounces) all-purpose flour
1 cup (7 ounces) granulated sugar
1/2 cup (1 1/2 ounces) cocoa powder
1 teaspoon baking powder
1/2 teaspoon baking soda
1/2 teaspoon salt
3/4 cup whole milk
1/3 cup canola oil
1 large egg
3 tablespoons unsalted butter, melted
1 teaspoon pure vanilla extract
For the Filling:
1/2 cup whole milk
2 tablespoons all-purpose flour
1 teaspoon cocoa powder
6 tablespoons (3 ounces) unsalted butter, room temperature
2 tablespoons vegetable shortening
1/2 cup (3 1/2 ounces) granulated sugar
1 teaspoon pure vanilla extract
2 ounces bittersweet chocolate, melted
To Make the Cakes: Adjust oven racks to upper-middle and lower-middle positions and preheat oven to 350°F (175°C). Line 2 baking sheets with parchment paper.
In a large bowl, whisk flour, sugar, cocoa, baking powder, baking soda, and salt; set aside. In a medium bowl, whisk together milk, oil, egg, butter, and vanilla. Pour wet ingredients into dry and whisk until smooth.
Using a 1 1/2 ounce ice cream or portion scoop, scoop out 18 to 20 mounds of batter on prepared sheets. Bake until firm to touch, 8 to 9 minutes, rotating pans from top to bottom and front to back halfway through baking. Transfer parchment sheets (with cakes still attached) to wire rack to cool completely.
To Make the Filling: In a small saucepan over medium heat, whisk milk with flour, cocoa powder, and salt until combined. Cook, gently whisking, until mixture thickens and just begins to boil (one to two large bubbles will pop to surface). Cover with plastic wrap and let mixture cool to room temperature (see notes).
In the bowl of a standing mixer fitted with whip attachment, whip butter, shortening, sugar, and vanilla on medium-high speed until fluffy, about 2 minutes. Add cooked flour mixture and continue to whip until very light and fluffy, about 5 minutes. Reduce speed to low and mix in melted chocolate (see notes).
Divide filling between half of the cakes. Sandwich together with remaining cakes. Serve.
Make sure to cover the cooked flour mixture with plastic wrap so that it doesn't develop a skin on the surface.
If, after whipping, the cream seems too soft to fill the cakes, chill it in the bowl for a few minutes to firm up a little, then whip again.
|Nutrition Facts (per serving)|
|Amount per serving|
|% Daily Value*|
|Total Fat 28g||36%|
|Saturated Fat 12g||59%|
|Total Carbohydrate 65g||24%|
|Dietary Fiber 3g||10%|
|Total Sugars 35g|
|Vitamin C 0mg||0%|
|*The % Daily Value (DV) tells you how much a nutrient in a food serving contributes to a daily diet. 2,000 calories a day is used for general nutrition advice.|