Cookie Face Lollipops

For a person that is traumatized by the act of rolling out dough, I sure picked a heck of a project for my son’s recent birthday. Several years ago, my mother made these adorable sugar cookies perched atop popsicle sticks for my son’s play group. Each cookie had its own little personality and people went crazy over them. I thought it would be fun to try to make cookies that actually looked like my son’s classmates and bring them in for his birthday. Though the project had enough missteps to dissuade me from trying to make them completely personalized, they came out really cute and some kids actually got cookies that looked like them without my even trying! One girl even had blue ribbons in her hair, just like the cookie. This is a rather big commitment of a project. I did it over the course of two days.

  • 1 cup (2 sticks) unsalted butter, at room temperature
  • 1 cup granulated sugar
  • 1 large egg, beaten
  • 2 teaspoons pure vanilla extract
  • 3 cups all-purpose flour, plus more for rolling out dough
  • 1/8 teaspoon kosher salt
  • 1/4 teaspoon baking powder
  • Cocoa powder, optional (see tips) for making varied “skin” tones
  • Mini M&Ms, for the eyes
  • 2 recipes Easy Frosting
  • Supplies: wooden popsicle sticks, pastry bag with various tips for hair, lips, etc., food color, cellophane bags (optional)
  • Preheat the oven to 350 degrees F. Lined a baking sheet with parchment paper.
  • In a stand mixer fitted with the whisk attachment, beat the butter and sugar together until light and fluffy. Add the egg, vanilla, flour, salt and baking powder. Continue beating until a slightly sticky dough comes together.
  • Turn the dough out onto a liberally floured surface. Apply a little flour to a rolling pin and to your hands, then roll the dough out until it’s about 1/8 inch thick. Cut out circles (I used a round cookie cutter that was about 3″ in diameter). Gently lift the cut outs onto the baking sheet lined with parchment. For each cookie, you will need to use two cutouts. Place the first on the baking sheet, then set a popsicle stick so the top 1/4 is firmly on the cookie. Place the second cut out on top, then press lightly to adhere. Continue in this manner until your cookie sheet is full. My baking sheet accommodated about 8 assembled cookies.
  • To make the eyes, select the appropriate eye colors from the mini M&Ms. I used typical eye colors – blue, green and brown – but if you don’t want to be so precise you can use all the colors. Press the eyes into place gently. I made sure the “m” was facing down.
  • Bake for 13 minutes, then allow to cool on the pan for a few minutes. Carefully transfer cookies to a baking rack to cool completely. If you will not be frosting them until the next day, keep them lightly covered with plastic wrap until you are ready to frost them.
  • To frost the cookies, first prepare various colors of the easy frosting recipe. I used a beige color, yellow and a dark chocolate frosting for hair. Having these ready before you begin is helpful. Lay the cookies out on a work surface lined with wax paper or parchment (to catch spills). You can get very creative with the hair and facial expressions! I had fun giving these cookies personalities. It might have been the only fun I had over the course of this project.
  • Allow the frosting to dry completely before moving the cookies. I used cellophane bags to keep them fresh (they weren’t closed, but this helped) and make transporting them a little easier. My good friend Eleanor ingeniously cut slits into a block of styrofoam and stuck her finished cookies into the slits for easy transport. Brilliant!
  • Quick Tips
  • 1. I really wanted to make a range of “skin tones.” I first tried to divide the butter and sugar mixture into thirds and separate the flour into cups. This was a bad idea since I just eyeballed the butter/sugar but measured the flour. I added about 1 tablespoon of Valrhona cocoa powder to one-third of the flour for “dark,” about 1 teaspoon of cocoa powder for “medium” and nothing for “fair.” The doughs were unevenly moist and in general, a big mess. The lesson learned here is that you need to make separate batches of dough to make varying shades of skin tones. Experiment with the cocoa powder to get the shades you want, but I found that about 2 teaspoons per full batch was about right for a “medium” skin tone.
  • 2. The yield is sort of difficult to describe here. I ruined my first batch of dough by trying to split it evenly into thirds, so I only got about 1/2 the amount of cookies I needed from that batch. I made a second batch and got enough to make about 16 completed cookies (32 cut outs in total). I highly suggest either splitting the batch in half and making two colors that way, or just making two batches depending on how many cookies you need to have. Or maybe all the people you know are the same color in which case you will not need to fuss over any of this nonsense. I ended up with 25 completed cookies with about 1-1/2 batches.

Preparation time: 3 hours if you’re fast and don’t have to keep going to the store for more powdered sugar

Cooking time: 1 hour

Number of servings (yield): 28-32 cut outs


3 responses to “Cookie Face Lollipops”

  1. Queen Bee says:

    I couldn’t believe you were undertaking this project because I know how labor intensive it is. I recall asking you to help me make the mushroom cookies at Christmastime and you couldn’t finish the batch as a helper!

    • Alicia says:

      Mom, will you remind me of this next time I get a hare-brained idea to do something insane such as this? I am clearly not hard-wired for tedious projects. However, just this morning a certain someone asked me when we’ll be starting our annual gingerbread house AND if this year we could make a gingerbread airport?

  2. Jen Mirilovich says:

    Thanks so much for the sugar cookie recipe! Used it last night to make pumpkin cut-out cookies for my 3rd graders class, the recipe I’d been using was impossible to roll out and thought I’d try something new. This worked great and they were delicious!

Leave a Reply

Your email address will not be published. Required fields are marked *

Want to receive updates in your inbox?