Preheat the oven to 350°F/180°C/Gas 4. Line cupcake pans with 16 black cupcake liners and set them aside.
Using an electric standing or hand mixer, beat the cake mix, eggs, milk, and butter until combined and smooth. Fold in the crushed Oreos.
Use an ice cream scoop to divide the batter between the cupcake liners. Fill about ¾ full.
Bake in the preheated oven for 20 minutes or until an inserted toothpick comes out clean.
Remove the cupcakes from the oven and leave to cool in the pan for 5 minutes before transferring to a wire rack to cool completely before decorating.
To Make the Penguin Faces
Line a large cookie sheet or tray with parchment paper or a non-stick baking mat and set it aside. When using fondant, use cornstarch as you would flour when making dough. Dust your work surface, hands, and tools. Knead your fondant before using it to make it pliable.
Roll out white fondant to ¼"/0.5cm thick. Use a 2"/5cm heart-shaped cookie cutter to cut out 16 hearts. These will form the penguin's face. Place on prepared cookie sheet.
To Make the Penguin Hats
Roll out red fondant to ¼"/0.5cm thick. Use a 3"/7.5cm round cookie cutter to make 16 circles. Then use the cutter again on the circles to create crescent moon shapes for the penguin's hat. Place on prepared cookie sheet.
Roll out more red fondant and use a small circle plunger to cut out 16 circles. Brush the back of each small circle with some edible fondant glue or a little water to stick it to the top center of each red fondant hat.
Pinch off 1 tablespoon of red fondant and roll it into a thin sausage approximately 3"/7.5cm long. Repeat to make 32 in total. These will form the hat's trim.
Take one end of two sausages and pinch them together. Twist to create a braid-like trim. Dab edible fondant glue or water along the bottom of the hat and position the trim in place. Lightly press to secure and trim off any excess on either end. Repeat to complete all of the fondant hats. Set aside to dry while the cupcakes are cooking and cooling, and while you make the frosting.
To Make the Frosting
Use an electric stand or handheld mixer and add the butter, powdered sugar, cream, and vanilla to the bowl.
Beat on medium speed until creamy, smooth, and stiff peaks form.
Scoop ½ cup of frosting into a bowl, add 4 drops of orange food coloring gel, and stir to combine. Add more coloring if needed to reach the desired shade.
Transfer the orange frosting to a piping bag fitted with a small round tip and set it aside.
Add black food coloring gel to the remaining frosting. You may have to add upwards of 5-7 drops to achieve a nice, black shade. Add more as required.
Transfer ½ cup of black frosting into another piping bag fitted with a small round tip and set it aside.
To Decorate Cupcakes
Use a medium ice cream scoop to place a mound of black frosting on each cooked and cooled cupcake. Use a small angled spatula to flatten and create a smooth surface.
Place the white fondant hearts onto the lower part of the cupcakes.
Use the piping bag of black frosting to pipe eyes in the top part of the heart.
Use the orange frosting to pipe a small cone to create a beak.
Place the red fondant hats on top, pressing gently to secure. Use edible glue or water if needed.
You can finish here or decorate with single sprinkles. Dab edible glue onto the back of a holly or snowflake sprinkle, and add to the hat. Place them along the trim or at the top of the hat.
Serve, and Happy Holidays!
Notes
Prep Time: Have all ingredients at room temperature to ensure a smooth batter.
Decorating: Work quickly with fondant to avoid drying.
Colors: Use different colored fondant for the penguin hats. Green and blue work well for this time of year!
Storage: Place cupcakes in an airtight container to keep them fresh.