Jack Skellington Whoopie Pies

Skill Up Skillets month of Nightmare Before Christmas continues with a mouthwatering reverse whoopie pie recipe- a white cake cookie on the outside with rich, decadent chocolate on the inside. What’s even better, the center is filled with two different kinds of chocolate: homemade creamy chocolate ganache and a chocolate-chocolate chip whipped cream. The itty bitty Jack Skellington faces turned out to be rather adorable, and they’re so easy to make! Why are you not in the kitchen already?!

Don’t forget to head over to CuppaGeek to see what she has to offer for some spooky good Halloween teas. They’re simply to die for! Yes, I’m very punny, thank you very much. I think her Pumpkin King tea review would be spot-on for this recipe!

After a hysterical conversation with one of my international friends I learned that whoopie pies are an American thing. Seriously, I’d post the whole conversation here if I didn’t think she would hop on a plane to Ohio and beat me senseless with a rolling pin or something. A whoopie pie is a US baked good that is made of two round mound-shaped pieces of chocolate cake, or sometimes pumpkin or gingerbread cake, with a sweet, creamy filling or frosting sandwiched between them. You can learn more about whoopie pies here, if you’d like.

Boys and girls of every age… wouldn’t you like to bake something strange (and wonderful)?

Gamers, grab your mats:

WHOOPIE PIES:

• 1/2 cup (1 stick) softened butter
• 1 cup sugar
• 1/2 teaspoon baking soda
• 1/4 teaspoon salt
• 1 egg
• 1 teaspoon vanilla extract
• 2 cups flour
• 1/2 cup buttermilk
• black decorating icing

Recipe adapted from Better Homes and Gardens.

CHOCOLATE GANACHE:

• 6 oz. baking chocolate, I used semi-sweet. Also, holy shit, Ghirardelli’s was on sale! Eff to the yes!
• 1/2 cup heavy whipping cream

CHOCOLATE-CHOCOLATE CHIP WHIPPED CREAM

• 1 cup heavy whipping cream
• 1/2 cup sugar
• 1 tablespoon cocoa powder, I used Hershey’s Special Dark
• 2 oz. baking chocolate or mini chocolate chips

I just discovered the secret of small buttermilk containers. Shut up.

Preheat your oven to 375 degrees F and line a baking sheet with parchment paper.

In a large bowl, beat softened butter with your electric hand mixer for about half a minute. Because I’m perpetually that idiot who forgets to take the butter out of the fridge to soften it, I found a shortcut: microwave your wrapped butter stick on 50% power for 7-10 seconds. Works every time.

Hey look I did the thing.

Add your sugar, baking soda, and salt to the bowl and beat until combined, scraping down the sides of the bowl as needed.

‘As needed’: See also, ‘once’.

Add vanilla and egg and beat again to combine.

Well shit, the part where it starts to really taste good.

Now for the alternating part: We’ll be adding flour in three batches and buttermilk in two batches. Start by dumping in 1/3 of your flour and beat until just incorporated:

-fwump-

Next, half of your buttermilk. That’s 1/4 cup, if you care to measure. Beat until just incorporated.

Buttermilk: the nasty liquid that only tastes good in baking.

Flour again, half of what’s left. Beat, beat, beat.

It took me two minutes to sort out the pictures like, which addition is this?!

Last bit of buttermilk. Beat.

Seriously, have you tried to sip straight buttermilk? Ew.

Finally, the last of the flour. Beat until just combined. This is what the finished dough should look like:

Like tasty.

Drop small spoonfuls of dough onto your parchment lined pan(s) 1-1 1/2″ apart. However many you make, remember that whoopie pies have a top cookie and a bottom cookie. I ended up with 16 whoopie pies, or 32 total cookies. I would have had 17, but god forbid people leave a tray of cooling cookies alone.

#bakingproblems

Bake for 7-10 minutes, depending on your cookie size. Keep an eye on them. Cookies are ready when the bottoms are lightly browned and the tops are just set.

Baking tray #1

Allow cookies to cool in pan for 5 minutes, then transfer to a wire rack to cool completely. Dig that clumsy thumbprint in the bottom middle cookie.

While those are cooling, make up your ganache and whipped cream. for the ganache, plunk 6 oz. baking chocolate in a small pot with 1/2 cup heavy whipping cream. Turn your burner to low and stir with a spoon or spatula to prevent chocolate from burning.

Pretty sure this was taken at 4% battery life.

Remove from burner when chocolate is almost melted and stir or whisk until ganache is smooth. Set aside to cool for at least 15 minutes.

Don’t laugh at my spatula, dammit.

For the whipped cream, add whipping cream, sugar, and cocoa powder to a large bowl. Beat the living crap out of this with an electric mixer (please tell me you washed the beaters first) until mixture is thick and holds its shape.

Sometimes a smaller bowl is not better. I had to use my hand as a splash guard.

Finely chop 2 oz. baking chocolate. The chocolate should look more shaved than chopped.

Fancy baking chocolate woo!

Fold chocolate in to whipped cream with a spatula. Alternatively, you can use the ultra tiny chocolate chips, but considering that baking chocolate bars come in 8 oz…. 6 + 2 or buy something extra. You do the math.

I will enjoy my fancy-shmancy baking chocolate, thank you.

Transfer whipped cream to a piping bag with a #32 star tip. Refrigerate. Transfer chocolate ganache to another decorating bag. I would not put the ganache in the fridge.

Pipe expressive Jack Skellington faces on half of your cookies. For this, I recommend using two tubes of black decorating icing: one fitted with a #3 tip, one fitted with a #5 tip. Outline Jack’s eyes and pipe the mouth, stitches, and nose with the #3 tip, then switch to your #5 to fill in the eyes and mouth opening. Use a toothpick to clean up your lines as needed.

Q: Where did you find so many expressions?

A: Google. Always Google.

Outlining.

More outlining. So much fun with outlining.

And filling in. The icing sets up in practically no time.

Flip over your plain cookies and pipe whipped cream in a swirl motion on the flat inner surface. Your filling should not go all the way out to the edge or you’ll regret it. For the ganache, pick up your Jack-faced cookies and pipe a small amount in a swirl on the flat inside:

Seriously, this is all you need. You could even go a little lighter on the whipped cream.

Gently press your Jack-faced cookie onto your whipped cream cookie to make a sandwich. Be careful to not let the filling spill over the edge. Honestly, this is the hardest part of the recipe if that tells you anything at all. You’re done! Pop your finished whoopie pies in the fridge for at least 30 minutes before serving so the filling sets up properly. A cold whoopie pie is a happy whoopie pie.

The many faces of Jack Skellington

A delightful duo.

There you have it: spongy vanilla cake cookie, dual chocolate fillings, and fanciness. See, you can have it all! While you’re here, don’t forget to exercise your voting rights by choosing November’s Featured Recipe! Voting continues throughout the month of October.

Coming Up Next: Sally’s Blueberry Scones

Cheers,

Leisel

Remember, cooking IRL doesn’t have to be a Feat of Strength!

Entry for #WeeklyChallenge for #FoodBloggers