My poor Mother. Years ago, after she and my Dad got divorced and she was dating, she had our future Step-Dad over for dinner and dessert. She cooked and baked all day, and make one of her favorite cakes – – Pineapple Upside-Down Cake.
When her date arrived, after a bit of small talk, she asked the fatal question that will never be forgotten….she said and I quote the conversation….”So, what is your least favorite cake in the whole world?”
Her date had no idea of what he was getting into. He should’ve made something up. Anything. ‘Possum Cake would’ve sufficed.
But nope. He had no clue of what was about to happen.
There was an overly long, uncomfortable pause….and finally….he said….
“Pineapple Upside Down Cake”.
And there it was.
The one wrong answer of a 1,000 different cakes to choose from.
The one cake that my Mom made that fateful day.
“Pineapple Upside-Down Cake.”
Yep. I was maybe 10 years old, my sister two years younger. We of course thought it was the funniest thing that ever happened in our lives and laughed ourselves silly. We were kids. We were good at it.
And it was probably just the medicine for the situation that probably kept my Mom from otherwise bursting into tears.
None of us all ever forgot that incident. (It really was pretty funny.) But I do still feel bad for her. Could you imagine? And he was in just as bad of shape.
Murphy strikes again!
But I’ve always loved this classic cake, as does my own husband, but the only thing I don’t like is that, the cake is always so thin if you are making it in a round pan versus one large one in a 13×9 pan. I’m more of a layer-cake kind of girl myself!
So instead of using half of the batter to make cupcakes, I decided to go ahead and try making a double layer one with a creamy filling in the middle instead.
I LOVE whipped cream with cake, and it helps to not only keep the cake itself a bit more moist longer, but a little fluffy whipped cream with each bite is such a treat, too!
You could also do two complete cakes with pineapple and cherries added to both layers, but I was afraid that, that could end up being a bit much. As well as being just way too sweet. So only one layer got the royal treatment.
I also dolled it up with coconut and finely chopped pecans, and more coconut and pecans into the cake batter itself for extra flavor. Added vanilla, butter rum flavoring, and the sweet juice from the can instead of all water added extra goodness to the cakes as well as an extra egg yolk.
And of course, butter. Melted butter in place of the oil definitely went in!
This turned out to be THE BEST Pineapple Upside-Down Cake that I’ve ever had! Especially from starting from a simple box. Though nothing compares to “from scratch” cakes, this is a VERY close second that I’m more than proud to share and would feel comfortable bringing to someone’s house.
So if you too are a Pineapple Upside-Down Cake lover, and even if not and maybe want to give it a second chance, this recipe is one you’ll really enjoy! It’s loaded with goodies and the whipped cream just adds extra fun and the creaminess it deserves! I simply used a tub of Cool Whip that has been mysteriously sitting in the freezer for quite some time, and that worked really well actually, because it doesn’t melt, weep and turn into a liquid mess. It held up beautifully until the cake was finished after several days being stored in the fridge.
So keep this beauty in mind for a pretty, fun and nostalgic cake for any upcoming occasion! It’s a step above the usual classic, and really makes for a beautiful presentation loaded with whipped cream and done in two layers! But you might want to check with your date first to make sure it’s not the one cake he doesn’t like. Jus’ sayin’.
Take care all and have a spooktacular weekend! Happy Halloween! ~Kelly
- 4 Tbl. (1/2 stick) real butter, melted
- ½ cup dark brown sugar
- 7 pineapple rings, (from a 20 oz. can in heavy syrup, *reserve syrup)
- 7-10 maraschino cherries, halved
- 2 Tbl., packed, sweetened flaked coconut
- 1 (16.5 oz.) box white or yellow cake mix
- 3 eggs plus one egg yolk, (even if the box says differently)
- heavy syrup from can plus enough water added to equal 1 cup
- 5 Tbl. melted butter
- ¼ cup packed coconut
- ¼ cup finely chopped pecans
- 1 tsp. vanilla extract
- ¼ tsp. butter rum flavored extract
- 1 (8 oz.) tub Cool Whip, thawed
- Spray 2 (9") non-stick cake pans with butter-flavored no-stick spray. (I use Crisco's.)
- Melt 4 Tbl. butter and spread into bottom of one 9" cake pan.
- Sprinkle dark brown sugar over the melted butter and evenly pat firmly.
- Decorate with pineapple rings and halved cherries (cut side-up), on top of the brown sugar. Sprinkle with coconut, especially into the gaps. Set aside.
- In large mixer bowl, add rest of ingredients except Cool Whip. Beat on low to mix, then medium for 2 minutes. Pour into cake pans.
- Bake cakes at 325 degrees for 33-35 minutes until done. Turn out cake with pineapple rings after resting on cooling rack for 5 minutes.
- Turn out second cake after resting 10 minutes. (You may need to tap the edge of the cake pan on the cooling rack to get cake to release.)
- Let cakes cool completely. Place plain layer onto serving plate or cake stand. Top with Cool Whip.
- *CAREFULLY place second layer on top centering before setting down gently. (Get all four fingers spread open under cake with both hands to keep it perfectly stable.)
- **To slice easily: Use a very sharp knife and cut by sawing straight up and down, not back and forth horizontally.
- Stays fresh and moist for 3 days. Best and easiest sliced after chilling.
- Store covered in refrigerator.
**I used my Calphalon cake pans that are no-stick. If you're afraid of the cake sticking to your pans, spray ONLY the one pan that calls for the butter, brown sugar and fruit. But for the plain cake layer, you might want to lightly flour it in addition to spraying it (or using shortening instead of spray.) I had no trouble getting my cakes to release from my pans, though.