Heather and the Three Pineapple Upside Down Birthday Cupcakes

I've decided that all my friends should have birthdays in the near future because I'm thoroughly enjoying opening up Terry's Crafty Confectionery Crafts (working title) for doling out birthday treats (see Alexis and the Baked Alaska). Up today is Heather, the physical therapist/ former collegiate goalie and expert potato stuffer who often enjoys plundering my baked goods, falling asleep on my couch and laughing at my cursing and pacing during Saints games.

Three varieties for triple the birthday fun!

Heather gave me several starting points for her birthday. She likes pineapple upside down cake, cupcakes and cream cheese frosting. After the hamster on a wheel that controls my brain got spinning, I came up with the ultimate solution: 3 distinctly delightful pineapple upside down cupcakes. The first would be a mini version of a pineapple upside down cake, while the next two would be more of your garden variety cupcakes with pineapple filling and a cherry cream cheese or whipped cream frosting.

Pineapple Upside Down Cupcakes 
Adapted from TasteofHome.com
Servings: 24 cupcakes
Time: 45 minutes (plus all the ridiculous extra steps I put in)

6 tbsp butter, cubed
1 cup packed light brown sugar
2 tbsp light corn syrup
Pineapple slices
Maraschino cherries
3 eggs
2 cups sugar
1 cup canola oil
1 cup sour cream
1 tbsp vanilla extract
2 1/2 cups all-purpose flour
1/2 tsp baking powder
1/2 tsp baking soda
1/2 tsp salt
Frostings (see below)

1. Preheat the oven to 350.
2. Line the bottoms of a cupcake tin with wax paper and grease the sides well.
3. Melt the butter in a saucepan over low heat. Stir in the brown sugar and corn syrup and stir over medium heat until the sugar dissolves.
4. In a separate bowl, beat the eggs and sugar together until thickened and lemon colored.
5. Beat in the oil, sour cream and vanilla until smooth.
6. Sift the flour, baking powder, baking soda and salt together in a separate bowl.
7. Add the dry ingredients gradually to the wet ingredients and mix well.
8. Spoon the butter/brown sugar mixture onto the waxed paper in the cupcake tin.
9. Place a pineapple slice on top of the butter and fill the hole with a cherry.
10. Pour in the batter to fill the cup about 2/3 of the way.
11. Bake for 16-22 minutes or until the toothpick test comes back clean. Make sure you rotate once halfway through.
12. Let cool on a wire rack then top lightly with frosting (recipe follows).

A dollop of whipped cream covers up where I had to cut the pineapple.

These just might be the most adorable cupcakes I've made yet. They really are just a mini pineapple upside down cake, so you get all those same wonderful flavors in a convenient handheld package. The top (or bottom in this turvy topsy world) is phenomenal. The brown sugar and butter bakes into this perfect sugary layer that meshes spectacularly with the pineapple and cherry (In my ravenous haste, I ate the pineapple first and was left with a sad fruitless/sugarless cake.). My only gripe is that they aren't really a traditional cupcake. Where's the wrapper?!? So I remedied these feelings of not having truly made cupcakes to satiate my inner crazy by also changing things up for a more typical approach (if you count filling and two kinds of frostings as typical).

Pineapple Upside Down Cupcakes (Traditional)

So here's where it gets tricky, readers. If you want more of a traditional cupcake (one in a cupcake wrapper) then disregard steps 2, 3, 8 and 9 from above. Instead just make your batter and pour it into the lined tins. Then after baking, add in some pineapple filling (recipe follows) and garnish with frosting, chopped pineapple and a cherry.

Lining the bottoms with the brown sugar mixture results in a weird divided cupcake with the brown sugar stuck to the wrapper (which is why we skip these steps). Luckily I made a dozen without doing this.

My first attempt incorporated the butter/brown sugar glaze that usually sits on top of a pineapple upside down cake. Unfortunately, this hardened on the wrapper and caused a strange divide with the batter, so you essentially had two non-touching layers (and one very structurally unsound cupcake that would be condemned). I figured this might happen, so I also prepared some without the butteryness. They were absolutely incredible and a completely different experience from the original recipe allowing you to have two awesome and distinct desserts with minimal extra effort (plus the filling could be eaten by the gallon on its own so you should make it anyway). The cake itself had a somewhat crispy exterior (which I've noticed happens with the foil cupcake liners I've been using) that lent some nice texture to the inner moist cake and pineapple filling, while the frostings brought the sweetness to near dangerous levels of delectability (Danger Zone!).

Pineapple Filling
From Food.com
Servings: About 2 cups
Time: 20 minutes (plus chilling)

1/2 tsp salt
3 tbsp cornstarch
1/2 cup + 1 tbsp sugar
20 oz can crushed pineapple, in its own juice
3 tbsp butter

1. Combine the salt, cornstarch, salt and pineapple with juices in a heavy saucepan.
2. Bring the mixture to a boil over medium heat stirring constantly.
3. Let boil for 5 minutes while stirring until it thickens and no longer looks milky.
4. Remove from heat and stir in the butter until melted.
5. Let cool then refrigerate for at least an hour.

This seriously reminds me of some cake from McKenzie's growing up, but I have no idea what its name was (and it's driving me insane). Update: my mom came through in the clutch and remembered it's the Pineapple Delight.

My favorite part of all this cupcakery was definitely the pineapple filling. It instantly reminded me of this cake I used to eat at my grandmother's as a small child (which I sadly can't remember the name of, because I'd definitely spend a week living off of that cake if I knew what it was). Part of me wanted to hollow out the insides completely just to maximize the amount of pineapple.


Cherry Cream Cheese Frosting
From AmandasCookin.com
Servings: Enough for all the cupcakes
Time: 5 minutes (plus chilling)

16 oz cream cheese, softened
1 stick unsalted butter, softened
1/3 cup cherry pie filling
1 tsp almond extract
1 tsp vanilla extract
2-2 1/2 cups powdered sugar

1. Beat the butter and cream cheese together.
2. Add in the cherry pie filling, almond extract and vanilla extract and beat until the cherries are broken into small pieces (about 1-2 minutes).
3. Add the powdered sugar about 1/2 a cup at a time until you reach the desired consistency and sweetness.
4. Refrigerate for at least an hour to help the flavors develop.

I ended up making two frostings for these cupcakes- a cherry cream cheese and a whipped cream frosting. The whipped cream was a nice touch that most closely mimicked a true pineapple upside down cake, but wasn't exciting enough for my tastes (if you'd like to make it you can find a wonderful vanillay recipe for it here). The cherry cream cheese was definitely the way to go with either version of the cupcake. Cherry bits and the almond extract make this stand out from your usual cream cheese frosting (which is saying something because cream cheese frosting is already the greatest thing in the history of things). 

Good to know, cupcakes can have pictures taken of them with candles but NOT with fireworks.

I was extremely proud of these cupcakes and relieved since they helped ensure Heather would remain my friend and Archer watching companion at least until her next birthday. If I had to pick a favorite, it would be the traditional cupcake with cherry cream cheese frosting by a hair over the mini pineapple upside down cake (complete with cherry cream cheese frosting, of course). Heather made sure to sample each one to refrain from insulting the chef (and I appreciate her valiant efforts).

As always, purchase of 2 dozen cupcakes comes with a free sexy pineapple hat.

Since this took quite some time to put together, I made these over the weekend ahead of her actual birthday which is Tuesday (and led to her comically chiming in with "in two days!" during the happy birthday song).  Hopefully, she's resisted the severe temptation calling to her from her fridge and managed to save some for her actual birthday (I'm pretty sure I'd have to tie myself down to accomplish that level of self restraint). 

Happy Birthday, Heather!