Sometimes life is confusing.

Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes I

You know.


Do blueberries taste good in mojitos?


Wait, really… did I buy these skinny jeans?


Do people really drink that wine after squishing the grapes between their stubby toes? Really… ?

Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes I

What’s gonna happen to Vincent Chase come September?


Do I want a cookie or a cupcake?


What was I smoking when I bought those jeans?


Can I get away with both a cookie and a cupcake?


How much longer must I ellipticize tomorrow if I have a cookie and a cupcake?

Or… two cookies.

And a cupcake.




Why didn’t the sales associate warn me that these skinny jeans came with the Fat Booth app built in?

Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes I

Ahhh. Life is darling.

And since I’m not quite prepared to discuss jeans that make you shimmy and shake and turn water into wine just to get a leg in or the impending finish of Vincent Chase we’re going to chat about these cupcakes.

I like these cupcakes. They have split personalities.

I made them look cute with bright sprinkles in a non-orderly fashion. And even cuter with a chewy cookie chunk shoved atop their fat frosting. Because they deffffinitely needed more calories. They have a chocolate chip cookie butt too. I like I like I like.

They were made for thatguyIlivewith* who promptly ate three after his well-balanced lunch of a double burger + a side of protein bar. And thatguyIlivewith* ate seven burgers this weekend. I’m requesting a new life insurance policy for thatguyIlivewith.*

Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes I

Chewy Chocolate Chip Cookie Bottomed Cupcakes

makes 18-20 cupcakes

cookie layer:

1/2 cup butter, softened

3/4 cup brown sugar, loosely packed

1 egg

1 teaspoon vanilla extract

1 1/3 cups all-purpose flour

1 teaspoon baking soda

1/4 teaspoon salt

3/4 cup chocolate chips

Preheat oven to 350 degrees F. Sift flour, baking soda, and salt together and set aside in a bowl.

Beat butter and sugar together in the bowl of an electric mixer until it’s light and fluffy. Add egg and vanilla and beat until combined. Add in dry ingredients and mix until just combined. Fold in chocolate chips. Line a muffin tin with liners and give each a quick spritz of non-stick spray. Using a spoon also sprayed with non-stick spray, press about 1 1/2 tablespoons of cookie dough into the bottom of each liner.

cake layer:

1/2 cup butter

1 cup white sugar

2 whole eggs

1 tablespoon vanilla extract

1 1/2 cups flour

1 teaspoon baking powder

1/3 cup milk

Preheat oven to 350 degrees F.

Cream butter and sugar in the bowl of an electric mixer until fluffy, about 3 minutes. Add eggs and vanilla and beat until combined.

Combine dry ingredients in a bowl. Add half of the dry ingredients, mixing until just combined. Add the milk. Once mixed, add remaining dry ingredients. Using an ice cream scoop, drop batter on top of cookie dough mixture. Bake cupcakes at 350 degrees for 15-18 minutes.

Top with you favorite frosting, sprinkles, and chocolate chip cookies.

Note: Vanilla frosting recipe HERE. I double the chocolate chip cookie recipe above and used the second half to bake cookies. That is what I threw on top of the frosting.

Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes I

*names have been changed to protect the innocent guilty.

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174 Responses to “Chewy Chocolate Chip Cookie Bottomed Vanilla Cupcakes.”

  1. #
    kyleen — July 13, 2011 @ 6:48 pm

    Those cupcakes are genius! Cookiecakes, now I don’t have to choose (:


  2. #
    Jenn — July 13, 2011 @ 7:29 pm

    Those are so sinful that I feel I must go to confession just for looking at them.


  3. #
    eli — July 13, 2011 @ 8:40 pm

    blueberry mojitos are delish! Just had one this weekend!


  4. #
    Rachel! — July 14, 2011 @ 12:13 am

    Made these for my best friend’s dad who is in the hospital, topped with a whipped cream cheese frosting and rolled in mini m&m’s. He LOVED them, and so did the nurses he bribed them with! Thanks so much (:


  5. #
    Brittany — July 26, 2011 @ 11:30 pm

    I am definitely making these as a treat-surprise for when my long distance boyfriend comes to visit this weekend! Can’t wait!


  6. #
    Candice — July 27, 2011 @ 10:08 pm

    I made these for the notoriously picky students at the school I work at (they rarely eat the stuff I bake and bring in) but these FLEW! Figures, the one time I don’t make a double batch. I will definitely be making these again!


  7. #
    Maria — October 28, 2011 @ 10:28 am

    I love your site and the way you word everything its not only fun to read but the recipies are great n look amazing i think this is my fav website thanks!!!keep up the good work


  8. #
    Christine — November 23, 2011 @ 4:53 pm

    One word: yum. I made these for my friend’s surprise 25th birthday and everyone loved them! My only complaint is that while baking them I of course had to lick the bowl, then try a cookie, then a cookie with the frosting, and then an actual cupcake. So good but I was definitely in a sugar coma for a few hours…guess I have to work up to Jessica’s sugar tolerance…I’m a novice baker for sure!


  9. #
    natalie — January 29, 2012 @ 12:08 pm

    made these last night and the tops completely caved in on themselves – what did i do wrong?? they tasted DELICIOUS though, as the most obvious solution was to fill the little holes with frosting :)


  10. #
    culinaryneophyte — February 6, 2012 @ 8:10 pm

    You are genius! I made these for my Super Bowl party, and they were gobbled up. Thanks for sharing! I will definitely make these again!


  11. #
    rose — February 12, 2012 @ 5:25 pm

    These look amazing and I want to make them for valentines.. just wondering if a boxed cake mix would work as the ‘cupcake layer’? I have one laying around…


  12. #
    Carolyn — April 19, 2012 @ 7:47 pm

    I combined these cupcakes with your cookie dough frosting.. DELICIOUS


  13. #
    Lucy — June 4, 2012 @ 10:47 pm

    Omg those look delish!!!


  14. #
    Danielle — July 20, 2012 @ 9:31 pm

    These are the most inventive cupcakes! I made mini cupcakes with this recipie, and ended up with a bunch of little half cookie, half cake treats. Definitley delicious (:


  15. #
    sally @ sallys baking addiction — August 26, 2012 @ 9:03 am

    Jessica – somehow I missed these cupcakes from last year! So glad you pinned them recently and so glad I … stalk you.. on interest! Ahh! Adding these to my cupcake repertoire. You are my go-to site for cute cupcakes, Love the way you plop the frosting on them too! :)


  16. #
    Ashley — August 27, 2012 @ 9:21 pm

    I love all of your recipes! I’m sure it’s simple, but can you share how you frost your cupcakes as pictured in this post/what tip you use? Thanks!


  17. #
    Drusilla — December 15, 2012 @ 9:25 am

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  18. #
    darling doll — August 30, 2014 @ 5:09 pm

    Ureka!!! That’s sooooooooo cool i cannot get over it i need to do this lifewise



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