Homemade Oatmeal Cream Pies

I had to save the best for last this week. Oatmeal Cream Pies were my all time favorite. There’s just something about that soft chewy oatmeal cookies with the cream filling smooshed between.

I have a confession to make about the store bought version of this cookie. When I was in High School, I was the yearbook editor senior year with a good friend of mine K. He and I had a class period each day to do yearbook work as an independent study class. We had the yearbook room to ourselves for one hour a day. It was a lot of fun. We kept Oatmeal Cream Pies in the yearbook drawer and would house these things on a regular basis. We’d go through a disgusting amount of these cookies in one hour. Thank goodness for my high-school metabolism (which has since vanished), as well as my stomach of steel. Oh man, parts of high school were a good time.

Back to reality. In the past 10+ years since then, my stomach has become more sensative to dairy and other foods, and I have to work to not gain weight. I’ve learned a lot about how to eat healthy and gained quite the love of cooking and baking. I’ve also learned that most store bought foods can be made a hundred times better at home.

These cookies are no exception. The brown sugar in the cookies keeps them perfectly soft and the filling is so much better than what’s in the store bought version. It’s like a homemade marshmallow fluff, and it’s amazing. I packaged them in celophane bags so they were easy to throw into lunches for me and Hubby this week.

One Year Ago: Best Dang Thing Ever Bars

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Homemade Oatmeal Cream Pies

Yield: 24


For the Cookies
3/4 cup unsalted butter, softened
2 cups packed brown sugar
2 eggs
1/2 tsp salt
2 cups flour
1 tsp baking powder
1 tsp ground cinnamon
2 cups quick-cooking rolled oats
2 tsp baking soda
3 Tbsp boiling water

For the Filling
1 Tbsp plus 1 tsp unflavored gelatin (about 1 1/2 packets)
1/3 cup plus 1/4 cup water (divided)
3/4 cup sugar
1/2 cup light corn syrup
2 tsp vanilla
1 cup powdered sugar
8 ounces vegetable shortening


Make the cookies
Preheat the oven to 425 degrees F. Lightly grease a baking sheet and set aside (or use parchment).

Cream the butter, sugar, and eggs in a large bowl.

In a separate bowl, sift together the salt, flour, and baking powder. Add to the creamed mixture. Add the cinnamon and oats. Mix well.

In a small dish, add the baking soda to the boiling water, and then stir the mixture into the rest of the batter. Mix well.

Drop by the tablespoon onto the baking sheets about 2 inches apart and bake until the cookies are firm and just starting to turn golden around the edges, 10 to 15 minutes. Cool the cookies on a wire rack or a plate.

Make the filling
In a small measuring cup, sprinkle the gelatin over 1/3 cup cold water. Let stand, stirring once or twice until the gelatin softens, about 5 minutes.

In a heavy 2-quart saucepan over medium-high heat, stir together the granulated sugar, corn syrup, and 1/4 cup hot water until well blended. Continuing to stir, raise the heat to high and bring to a full boil. Continue boiling for 30 seconds. Immediately remove from the heat. Stir in the gelatin mixture until it dissolves completely.

Transfer the mixture to a large bowl. Add the vanilla.

With a mixer on medium speed, beat for 20 seconds. Gradually raise the speed to high and beat until the mixture is stiffened, white, very fluffy, and cooled to barely warm, about 5 minutes.

Reduce the mixer speed to low and gradually add the powdered sugar.

Add the shortening and beat until completely smooth.

The filling will set up as it sits, so wait until it is thick enough to spread or pipe before filling the cookies.

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23 Responses to “Banana Split Cupcake”

  1. #
    stephchows — September 15, 2009 at 12:47 pm

    Great cupcake hero entry!!! yum!

  2. #
    oneordinaryday — September 15, 2009 at 2:04 pm

    You’re right – it’s a freaking cute cupcake! I especially love that frosting and how you got it to look like a scoop of ice cream. Nicely done!
    This is my first CH and I can’t wait till the voting begins! : )

  3. #
    Amanda — September 15, 2009 at 2:49 pm

    Wow, what a yummy looking cupcake! Great idea!

  4. #
    oneparticularkitchen — September 15, 2009 at 4:14 pm

    This is ADORABLE!! I love it!

  5. #
    Xiaolu — September 15, 2009 at 5:08 pm

    Gorgeous cupcake, Jen! I love how the cherry stands out. How do you get that black background if you don’t mind me asking? I’m pretty new to this food photography thing 8)

  6. #
    Amy Kingman — September 15, 2009 at 5:41 pm


  7. #
    Jen — September 15, 2009 at 5:51 pm

    Xiaolu – It’s actually just my black table. I’ve also had luck using a plain black piece of construction paper (most of my backgrounds are the 12×12 scrap-booking papers) or a black towel to get the background all black.

    Here is an example using paper, and one using a towel.

  8. #
    Xiaolu — September 15, 2009 at 5:59 pm

    Thanks! That’s really helpful.

  9. #
    Joanna — September 15, 2009 at 8:28 pm

    Yum! Great idea 🙂

  10. #
    Stephanie Wagner — September 15, 2009 at 10:44 pm

    Awesome idea!

  11. #
    bcallegra — September 16, 2009 at 2:04 am

    Very creative and it looks great!

  12. #
    The Novice Chef — September 16, 2009 at 3:15 am

    What a cute idea! I love it!! And I know my nieces would be in love!

  13. #
    nutmegnanny — September 16, 2009 at 3:33 am

    Great idea…they look delicious!

  14. #
    jesstyler — September 16, 2009 at 4:08 am

    holy deliciousness! I NEED one of those! 🙂

  15. #
    Kerstin — September 16, 2009 at 4:48 am

    How creative, I love them! So cute and tasty with that cherry on top!

  16. #
    Ingrid — September 16, 2009 at 3:14 pm

    Very cute looking! I like your idea.

  17. #
    lifeoftheparty — September 16, 2009 at 7:25 pm

    These cupcakes are pure genius… you’ve definitely got my vote!

  18. #
    Jigginjessica — September 17, 2009 at 12:34 am

    Cute idea! What a great entry!

  19. #
    thegreatpantryraid — September 17, 2009 at 7:37 pm

    Wow – super cute! A lot of work, I’m sure, but such a big payoff! Great job!

  20. #
    Kami — September 17, 2009 at 8:32 pm

    So stinkin’ cute!

  21. #
    Caroline — September 19, 2009 at 6:23 am

    Very cute, indeed and loving the pineapple in the frosting. I can just imagine how delicious this would taste. What a great idea.

  22. #
    Keiara Wells — September 19, 2009 at 5:57 pm

    MMM, it looks fantastic! I’ll have to try this one 🙂 xox

  23. #
    Sweet and Savory — October 15, 2009 at 5:55 am

    These cupcakes are precious besides, I am sure, being delicious. What a great idea.

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