Cakespy: Reverse Whoopie Pies Recipe


Quirky, cute, sometimes controversial, always delicious recipes from Jessie Oleson.

Cakespy: Reverse Whoopie Pies Recipe

Jessie Oleson (aka Cakespy) drops by every Monday to share a delicious dessert recipe. —The Mgmt.

[Original artwork and photographs: Jessie Oleson]

What's a Reverse Whoopie Pie?

Basically, if you can imagine a Milano cookie going through a Hulk-like transformation into a supersized sweet treat, you've got the right idea.

That's right: these cakey whoopie pies pack all the flavor of the classic chocolate-filled buttery cookie sandwich, but without making any pretense of daintiness. This is treat of such proportion that it requires two hands to hold and all of your stomach to handle. Of course, if you want an even Hulkier variation, add peppermint extract instead of vanilla (and maybe a dash of green food coloring for good measure) for a chocolate-mint variation.


Reverse Whoopie Pies

  • Yield:about 12 to 24 whoopie pies, depending on size


  • For the cookies
  • 1 cup (2 sticks) unsalted butter
  • 1 1/2 teaspoons salt
  • 2 teaspoons vanilla extract
  • 1 tablespoon baking powder
  • 1 1/4 cups granulated sugar
  • 3 large eggs
  • 4 1/2 cups All-Purpose Flour
  • 1 cup milk
  • For the filling
  • 4 cups (24 ounces) semisweet chocolate chips
  • 2 tablespoons light corn syrup
  • 4 tablespoons (1/2 stick) unsalted butter
  • 1 1/2 cups heavy cream
  • 1/8 teaspoon vanilla extract


  1. 1.

    Preheat oven to 400°F. Lightly grease (or line with parchment) two baking sheets.

  2. 2.

    Make the cookies: In a large mixing bowl, cream together the butter, salt, vanilla, baking powder, and sugar. Add the eggs one at a time, beating well after each addition. Add the flour to the wet ingredients alternately with the milk, beginning and ending with the flour. Mix as gently as you can.

  3. 3.

    Using an ice cream scoop, drop the dough onto the prepared baking sheets. Leave 2 to 2 1/2 inches between each cookie, for expansion.

  4. 4.

    Bake the cookies for 9-11 minutes, or until they’re barely set on top; they won't have browned on top but will have a dull look and will spring back when touched lightly. Cool them on the pan for 5 minutes, then transfer to a rack to cool completely.

  5. 5.

    Cool them on the pan for 5 minutes, then transfer to a rack to cool completely.

  6. 6.

    Place the chocolate chips, corn syrup, butter, and heavy cream into a large microwave-safe bowl (or a medium saucepan over low-medium heat). Heat in the microwave for 2 to 3 minutes, until the mixture is very hot. Stir until the chocolate melts and the mixture is smooth. Chill in the refrigerator, stirring occasionally, till the filling is cool room temperature. Remove from the fridge, and beat at high speed with an electric mixer until it lightens in color and thickens slightly.

  7. 7.

    Spread a generous amount of filling on one of the flat sides of the cookies; sandwich another half on top to form your pie. Repeat with the remaining pies.