Homemade Oreo Cookies

I promised you an oreo cake last week.

Remember that?

Did I tell you that homemade oreos would also be involved?

It's true.  I wouldn't lie about such things.

Last Friday, one of my dearest friends finally turned 21.  Which is quite the occasion if you ask me.  And pretty big occasions provide the best excuses for making...monstrous cakes.

So that's just what I did.

My original intent was to make some sort of booze filled cake to go along with the whole 21st birthday thing.  Seems logical, right?  I thought so.  But the birthday boy quickly shut that idea down with a request for an oreo cake.  Not wanting to disappoint, I immediately started gathering ideas and brainstorming for an oreo cake that I would deem worthy of a 21st birthday.  And being the logical person that I am, I quickly decided that the first step would be to make homemade oreos.  Obviously.

And so here we are.

I planned on posting both the cake (midnight chocolate cake with a whipped vanilla frosting) recipe and the oreo recipe all in one post.  But then I started it and realized I was overwhelmed.  Meaning that you would probably be more than overwhelmed.  Whatever that is.  So, I decided it would have to be a two part ordeal.  Luckily, you don't need a cake to make these delicious things worthwhile.

Dare I say they are waaaaaaaaaaay better than store bought oreos?

I dare.

homemade oreo cookies

Adapted from Flour Cookbook

Makes: 16-18 Sandwich Cookies   Prep Time: 15 minutes  Refrigeration Time: 3 hours 
Bake Time: 20-25 minutes  Total Time: 3 hours 40 minutes

{Printable Recipe}

Ingredients:
1 cup (2 sticks) unsalted butter, melted and cooled slightly
3/4 cup granulated sugar
1 teaspoon vanilla extract
1 cup semisweet chocolate chips, melted and cooled slightly
1 egg
1 1/2 cups all-purpose flour
3/4 cup Dutch-processed cocoa powder
1 teaspoon kosher salt
1/2 teaspoon baking soda

vanilla cream filling-
1/2 cup (1 stick) unsalted butter, softened
1 2/3 cup confectioners' sugar
1 teaspoon vanilla extract
1 tablespoon milk
pinch of salt

Directions:

1. In a medium bowl, whisk together the butter and sugar until well combined.  Whisk in vanilla and chocolate chips.  Add the egg and whisk until thoroughly incorporated.
2. In another medium bowl, stir together the flour, cocoa powder, salt, and baking soda until well mixed.  Using a wooden spoon, stir the flour mixture into the chocolate mixture.  The dough will have the consistency of Play-Doh.  Let the dough sit at room temperature for about 1 hour to firm up.
3. Transfer the dough in a 15-inch square sheet of parchment or waxed paper.  Using your hands, shape the dough into a rough log about 10 inches long and 2 1/2 inches in diameter.  Place the log at the edge of the sheet of parchment paper, and roll the parchment around the log.  With the log fully encased in parchment, roll it into a smoother log, keeping it at 2 1/2 inches in diameter.  Refrigerate for at least 2 hours, or until firm.  The log may settle and sink a bit in the fridge, so reroll it every 30 minutes or so.  (At this point the dough can be well wrapped in plastic wrap and stored in the refrigerator for up to 1 week or in the freezer for up to 1 month.)
4. Preheat the oven to 325° and butter or line a baking sheet with parchment paper.  
5. Cut the dough log into 1/4 inch thick slices.  Place the slices 1 inch apart on the prepared baking sheet.
6. Bake for 20-25 minutes, or until the cookies are firm to the touch.  Check them frequently after 16-17 minutes by poking them in the middle.  Let cool on the baking sheet until barely warm or right at room temperature. 
7. While the cookies are cooling, make the filling by beating the butter on low speed for 30 seconds in the bowl of a stand mixer (or with a hand mixer) fitted with the paddle attachment.  Add the vanilla and confectioners' sugar and beat until smooth.  Add milk and salt and again beat until smooth.
8. Scoop about 1 tablespoon of the filling onto the bottom of one cookie.  Top with a second cookie, bottom-side down, then press the cookies together to spread the filling toward the edges.  Repeat until all of the cookies are filled.