There are so many versions of the so-called “homemade” Oreo cookie. Everything from semi-homemade, which begin their cookie base from a boxed devils food cake mix to one of the original adaptions by Wayne Brachman. His book, Retro Desserts seems to be the catalyst to many of the various versions and attempts to recreate that amazing, dark, chocolatey cookie with the creamy middle.

Anyway, after perusing 100 recipes, I decided my pinwheel cookie recipe was pretty dang close to nearly everything I was reading. With a few of my own modifications and a little experimentation on the filling, I am here to share with you, version 101. I don’t know if it’s the best, or the easiest, or the most healthy. All I know is that I made these yesterday and assembled today and so far, I’m just glad I had enough left to actually take a picture. (PS. You all know I hate shortening, right? But this is one time that it’s a must. Trust me on that one.)

Oreo Cookies:

1 1/2 cups all-purpose flour – .40
1/2 cup bakers Dutch cocoa powder (3/4 cup regular cocoa powder works as well, but dutch is darker and deeper in flavor) – 1.00
1 1/2 sticks butter, softened – 1.00
1 cup sugar  – .50
1 large egg – .15
1 tsp vanilla – pantry
1/2 tsp baking soda – pantry
1/2 tsp baking powder – pantry
1/2 tsp salt – pantry

COST: $2.55

Whisk or sift together flour, cocoa powder, baking powder, soda and salt in a large mixing bowl. Set aside.

In a separate bowl, beat softened butter and sugar with a mixer at medium-high speed. Make sure sugar is well incorporated and mixture is nice and fluffy. If using a handheld mixer, this may take 5 minutes or more.

Once butter mixture is fluffy, beat in egg and vanilla, reducing speed to low. Add dry ingredients and mix until just combined. I prefer to do this by hand if using a handheld mixer. A spatula works just fine.

Once dough is combined, roll out with hands in a snake like fashion to the size (circumference) you want your cookies. Wrap in plastic wrap, chill until firm, at least 1-2 hours. (Note: if you’re in a hurry, you can toss in freezer for 15 mins and then in fridge for 15 to 30 more minutes. I know this works because I’m always in a hurry!)

When dough is ready and firm, preheat oven to 375°F. Cut 1/4 inch thick slices from chilled cookie log with a heavy knife and place on ungreased cookie sheet. Using your fingers, flatten each slice to desired thickness, about 1/8 inch. Bake cookies 8 to 10 minutes, depending on thickness. Cool for 1 hour before assembling.

Creamy Filling:

1/2 cup vegetable shortening – .50
2 cups powdered sugar (sifted) – .75
1/2 tsp vanilla extract – pantry
*Milk (you can add a tiny bit of milk if filling feels to stiff or tight)

COST: $1.25

Mix shortening, vanilla and sugar on low, just until combined. Turn blender or mixer to high speed and beat till light and fluffy. 2-3 minutes or so.

To assemble, you can use a piping bag or just spoon a tablespoon of filling onto one cookie and press the other to form an oreo sandwich. Nothing to it!

Now all you need is a big glass of milk, a cookie or 4 and start dunking! Delicious!

GRAND TOTAL: $3.80