CoPineSpiRum – A Mashup Of Coconut Cheesecake, Pineapple Upside Down Cake And Spiced Rum

Here we go again, another crazy day to celebrate this April.


April 20 is Pineapple Upside Down Cake Day! Why? We do not know. But let’s enjoy a look back to this vintage cake invented in 1903, but popularized in 1925 when the Hawaiian Pineapple Company (now the Dole Company) held a baking contest seeking pineapple recipes.


After seeing that so many people turned in recipes for pineapple upside down cake, company president Jim Dole decided to run with it and used the recipe to help sell his fruit. The cake peeked in popularity in the 1950s and ‘60s, but fell out of favor by the ‘70s and ‘80s when hippies and yuppies deemed it as too old fashioned.


This year, The Great Indoors will resurrect this classic dessert by amping it up a bit. I’ve chosen to add some flavors that complement pineapple including coconut and spiced rum. Meanwhile, I’m opting to ditch the maraschino cherries which traditionally sit atop the cake. (Does anyone really like maraschino cherries? In my opinion, nothing updates the look of this cake more than ditching those babies.)


This is a big cake – two layers of pineapple upside down cake sandwiching a coconut cheesecake. It’s reminiscent of mashup cakes we’ve made previously like the PumPecApple and the PieLogNog, so a little goes a long way. In the spirit of the mashups, we could call this Coconut Cheesecake Stuffed Pineapple Upside Down Cake with Spiced Rum Caramel. Or… “CoPineSpiRum.” Hmmm…maybe we’ll just eat it.


Coconut Cheesecake Stuffed Pineapple Upside Down Cake with Spiced Rum Caramel (a.k.a.: CoPineSpiRum)

Serves: 35


Plan ahead if you’re making this cake. It works best to make the coconut cheesecake the day before you plan to serve the dessert. That leaves ample time for it to chill. Another tip: always wrap your springform in foil to prevent leaking.

Coconut cheesecake layer
1 ½ cups graham cracker crumbs
3 ½ cups sweetened shredded coconut
1 tablespoon fresh squeezed lemon juice
4 (8-ounce) blocks cream cheese
4 large eggs
1 cup sugar
1/3 cup unsalted butter melted
1 (15-ounce) can cream of coconut
1 cup whipping cream
1 teaspoon vanilla extract

1 teaspoon coconut extract
Juice of 1 lemon

Pineapple Cake layers
1 (20-ounce) can pineapple slices in juice, drained
1 ½ cups spiced rum
2/3 cup butter
2 cups packed dark brown sugar
2 boxes yellow cake mix
1 cup piña colada mix
1 cup vegetable oil
6 eggs

For Coconut Cheesecake: Preheat oven to 325 degrees Fahrenheit. Wrap outside of springform pan with foil. Mix graham cracker crumbs, 1 1/2 cups coconut, 1 tablespoon lemon juice and butter in small bowl.

Press mixture onto bottom and up sides of pan. Beat cream cheese and sugar in large bowl until well blended. Add eggs – 1 at a time – beating well after each addition. Add cream of coconut, whipping cream, 1 cup coconut, vanilla extract, coconut extract and lemon juice; beat until well blended. Pour filling into crust.

Bake until set in center, approximately 1 hour 25 minutes. Transfer to rack and cool completely. Cover and refrigerate overnight. Cut around pan sides to loosen cake. Remove pan sides.

For Pineapple Cakes: Pour pineapple juice out of can of pineapple rings; set aside. Keep rings in the can and pour 1 cup of spiced rum into can. Let sit for at least one hour. Once soaked, take rings out of the can, but don’t throw away the rum.

Heat oven to 350 degrees Fahrenheit. Prepare first pineapple layer by combining one box of cake mix, ½ cup piña colada mix, ½ cup oil, 3 eggs and 1/2 cup reserved rum from pineapple. Beat with electric mixer on medium speed until smooth.

Pour mixture into greased springform pan wrapped in foil. Bake for approximately 40 minutes or until the center of the cake is no longer jiggly. Let cool.

Prepare the second layer of pineapple cake just like you did the first by mixing one box of cake mix, ½ cup piña colada mix, ½ cup oil, 3 eggs and 1/2 cup reserved rum from pineapple. Beat with electric mixer on medium speed until smooth. Put butter and remaining ½ cup of spiced rum in saucepan. Once butter is melted, add brown sugar and heat for about 1 minute or until it is foamy and bubbly, stirring constantly.

Put pineapple rings onto bottom of greased springform pan wrapped in foil. Pour a little more than half of the caramel sauce into the pan over rings. Pour batter on top of the caramel.

Bake 30 to 40 minutes or until cake springs back when touched lightly in center. Run knife around edges of cakes.

In the meantime, place plain pineapple cake layer on a plate followed by the coconut cheesecake layer. Finally, carefully invert the pineapple caramel cake on top so caramel drips down the sides. Take remaining coconut and make it into balls to put inside the rings. Drizzle remaining caramel over sides of cake. Serve warm with vanilla ice cream.