Chocolate Chip Brownie Pillows

Therese sent this one over a couple of days ago after finding it in an ad for the upcoming Southern Living Christmas edition. The cookies are interesting, fun, and big and sturdy enough to be wrapped individually for gift giving.  And by the same token, I think they’d be perfect for bake sales. For the sake of convenience, I used brownie mix brownies, but you could just as easily use leftover brownies from another recipe.


Chocolate Chip Brownie Pillows

1 (20-oz.) package double chocolate brownie mix
4 oz (1 stick) unsalted butter
1/2 cup shortening
1 1/2 cups firmly packed brown sugar
2 large eggs
1 egg yolk
1 Tablespoon vanilla extract
2 1/2 cups unbleached all-purpose flour (315 grams)
2 teaspoons baking powder
1/2 teaspoon baking soda
3/4 teaspoon salt
3 cups semisweet chocolate chips

Prepare and bake brownie mix according to package directions in an 8′ square pan. Cool completely, then cut brownies into about 3 dozen squares. You’ll only be making 11 giant cookies so you don’t have to cut all the brownies.

Beat butter and shortening at medium speed with an electric mixer until creamy. Add brown sugar, beating until smooth. Add eggs, egg yolk, and vanilla, beating until blended.

Combine flour and next 3 ingredients; gradually add to butter mixture, beating just until blended after each addition. Stir in chocolate morsels. Cover and chill dough 1 hour.

Preheat oven to 350 degrees F. For each cookie, scoop a level 1/2 cup dough onto parchment paper-lined baking sheets; place cookies 3 ” apart. Using your fingers, make an indentation in mound of dough; place 1
brownie square in center. Press chocolate chip dough around brownie; reshaping dough to form a ball.
Repeat procedure until remaining dough and 10 brownie squares, placing no more than 6 cookies on a baking sheet. Chill for 15 minutes.

Bake at 350 for 18 to 20 minutes or until lightly browned and cookies
look set. Cool 2 minutes on baking sheets; remove to wire racks, and cool completely.

Yield: 11 jumbo cookies.

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  1. Erin Kate says

    I’m curious, do the brownie pieces get crunchy getting baked that extra time?

  2. says

    Cookies like this are fun. After making last week’s TWD Chipster Topped Brownies (ccc on top of brownies), I decided I’d rather have a brownie in one hand and a ccc in the other. I’ve made little balls of brownie before, froze them, then baked them in a ccc. This looks like a fun way to bake in the middle!

  3. says

    Wow. Wow. I am gobsmacked! This may be the ultimate bakesale/gift cookie.

    I’m starting to think more evil thoughts–a chocolate chocolate cookie with a blondie in the center? Or a peanut butter cookie with a blondie in the center…this is true cookie madness at its finest!

  4. Therese B. says


    Wow, I feel so honored!! Thanks for posting the recipe. They really are great!
    And if you use the Girandelli…OMG…OVER THE TOP flavor!

    This will be one of keepers for sure!


    Yippee, Ms. Ginsberg made a recipe o mine!!
    tee hee!

  5. says

    Ok, we have been on tha same wavelength before, but this is getting TOO WEIRD! My officemate’s dear little 84-year-old mom, who is a terrific baker, sent me the BEST cookie yesterday via her daughter who left it on my desk at work. After one bite of the ginormous thing, I knew I wanted to make more right away. However, I have no time for anything other than pies at the moment (teaching another workshop at school tomorrow). But I thought, this is right up Anna’s alley–I should send her the recipe. So I signed onto to your site to post the suggestion, and what should your cookie o’ the day be but the same Chocolate Chip Brownie Pillows that I was going to send you! WEIRD!

  6. says

    Gina, that is too funny!

    Thanks for the comments, everyone. I can’t answer them all right now so I’m just going to answer the questions.

    Erin, the brownies stayed soft. I used brownie mix and baked it in an 8 inch pan so the brownies started off very tall and soft. They stayed that way.

    Therese, thanks again for the recipe. I have to admit, I used store brand brownie mix and the cookies were still great. Now that I know they’re good, I’ll use better brownie mix.

    Emily, thanks for the “beautiful” remark. They look even better in real life. Also, I didn’t chill my dough very long so I think when I bake up the next round using very cold dough, the cookies will look better.

    But overall I’d say they’re solid bake sale fare and are cute.

  7. says

    Wow, brownies and chocolate chip cookies rolled into one. You are so right about these being a bake sale best seller!

  8. says

    These cookies are driving me crazy — in a good way! They are a “must try” for next time I need to bake a batch for a group gathering. I think I’ll use the Ghirardelli triple chocolate brownie mix in mine. Can’t wait!!!!

  9. hulagirl247 says

    hi anna!

    leftover brownies????? is there such a thing???? i have several different bornies that i make and there are NEVER any leftover brownies. i’d have to bake a batch specifically for using to try this recipe. it sounds very yummy and looks delicious. just have to make certain that the brownies don’t disappear before getting to phase two! (maybe a good reason to do a triple batch of brownies!)

    will let you know if i ever succeed ~


  10. says

    I lost this recipe a few weeks ago and am so glad I found it here! I’m keeping my fingers crossed that I can actually make these because these really are the most divine cookies ever.

  11. Jen says


    what kind of shortening do you use in these cookies? I tried butter flavored crisco in cookies before but they tasted disgusting.

  12. says

    Hi Jen,
    I haven’t made these in a while and don’t remember if I used butter flavor or regular. However, I can see why you’d think that. Sometimes the butter flavoring in the BF Crisco can taste a little overwhelming. I have a few cookies where I’ve used it and regretted it. However, in some cookies the artificial butter flavor blends in or adds flavors people perceive as buttery.

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