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Boozy Pineapple Upside Down Cake

May 29, 2019

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Boozy Pineapple Upside Down Cake

Today would have been my Granny’s one hundredth birthday.  Sadly she’s been gone twelve years now, but I still think of her every day.  I hope she’s celebrating in style wherever she is, and I am here on earth, missing her smile and guidance, but still feeling it, and celebrating her.

One of the things I always remember her making was pineapple upside down cake.  Every gathering and party featured her cake that was quickly devoured.

By everyone but me.

Because I didn’t like it.

I’m so sorry Granny.

boozy pineapple upside down cake
boozy pineapple upside down cake

It was a texture thing with crispy pineapple edges, and I just couldn’t deal with it.  That’s why in all this time blogging, I also hadn’t posted it.  I thought I just didn’t like pineapple upside down cake.

But I wanted to make it in honor of Granny, and if I didn’t like it, I’d just give it away to friends.  Making this cake wasn’t about boredom (not that I am ever bored) or pleasing my own palate, it was about taking time to not just celebrate Granny, but channel her, remember her, feel her with me no matter how far she really is.

boozy pineapple upside down cake

After picking up a few ingredients, I got to work.  This is a labor intensive, multi-step recipe that I enjoyed making.  It’s an update to the classic cake.  I can’t say for sure how Granny made hers, but I assume like many pineapple upside down cakes, it contained cake mix, canned pineapple, and psychedelic maraschino cherries.

That is not this cake. 

It really starts with a super boozy syrup to add flavor to the pineapple and later soak into the cake.  Cakes with syrup soak will always be my jam.  Cakes with boozy syrup soak even more so.  The pineapple makes a mosaic in the bottom of the pan with fancy Fabbri cherries scattered about.

boozy pineapple upside down cake

Then there’s the cake batter that strangely doesn’t have any leavening.  This fact only occurred to me with a jolt of panic after I put it into the over, but at that point there wasn’t anything I could do so I rolled with it.

Instead of the pecans the original recipe called for, I sprinkled shredded coconut on top because pineapple and coconut are besties.

boozy pineapple upside down cake

The end result is a delightfully rich and decadent cake that has an acidic punch from the pineapple, a kick from the syrup, and a zing from the cherries, not to mention the crunch of the coconut that miraculously doesn’t need leavening.  Yeah, I kind of liked this cake.  Maybe my tastes have changed.  Dad really loved it.  Mom can’t eat pineapple (or apples even though they aren’t related), so we’ll trust Dad’s palate on this one.

I’m pretty sure Granny would have liked it too, but more than the cake, she would have liked it because I made it.  She would have liked sitting down to eat a piece with me over a cup of coffee and shared stories between us.

That was always what Granny liked the best: people, moments, life.  I like to think I got some of that from her too.

Granny!

It’s funny how time just keeps going.  How it feels like she died just yesterday and a lifetime ago all at the same time.  How I have some vivid memories of her but wish I remembered the sound of her voice, the way she smelled, how she moved.  How I wish we had time to talk and walk and cook and bake, learn from each other, just be with each other.

Love you and miss you, Granny, but I know you’re with me.  Keep an eye out for me if you can xoxo

Mom, Granny, and Me!

Boozy pineapple upside down cake

Pineapple and Glaze

½ cup packed light brown sugar

1 ½ cups bourbon

½ stick unsalted butter

½ pineapple cut into ¼ inch thick rings

Cake

1 ½ sticks unsalted butter, room temperature

¼ cup olive oil

1 cup granulated sugar

½ cup packed light brown sugar

4 large eggs

1 tablespoon vanilla bean paste

2 ounces pineapple flavored vodka

2 ½ cups all-purpose flour or gf or Paleo flour blend

½ teaspoon sea salt

¾ cup shredded unsweetened coconut

¼ cup Fabbri or Luxardo cherries

Make the pineapple and glaze.  In a medium saucepan, stir together sugar and bourbon.  Bring to a boil over medium heat and reduce to a simmer.  Simmer until reduced by about 1/3.  Remove from the heat and stir in the butter.  Stir in the pineapple and allow to soak 5 minutes.

Make the cake.  Preheat oven to 350 degrees F.  Oil a 9 inch round or square cake pan.  Arrange the pineapple in the bottom of the pan, filling in any gaps with the cherries.  Save the leftover glaze for later.

In a large bowl, cream the butter, oil, and sugars until light and fluffy.  Beat in the eggs one at a time followed by the vanilla and vodka.  Stir in the flour and salt.  Pour over the pineapple in the pan and sprinkle with the coconut, gently pressing it into the batter.  Place on aluminum foil in case some of the coconut comes off during baking.  bake about 1 hour 10 minutes, until golden brown and a toothpick inserted in the center comes out clean or with a few moist crumbs.  If the cake becomes too brown at any time, tent it with foil.  I did this after 30 minutes.

Allow the cake to cool about 10 minutes in the pan before inverting carefully onto a serving platter.  Allow to cool completely.  Serve with the leftover glaze.  Cake may be stored in an airtight container at room temperature for up to 3 days.

Recipe adapted from Kris Wessel via Epicurious

Filed Under: Cake Tagged With: Cake, Dessert, pineapple

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Comments

  1. Karen (Back Road Journal) says

    June 5, 2019 at 9:04 am

    What a sweet tribute to your grandmother. I’m sure she would approve of your delicious cake.

    Reply
    • Laura says

      June 7, 2019 at 3:56 pm

      Thanks, Karen!

      Reply
  2. John / Kitchen Riffs says

    June 5, 2019 at 9:49 am

    Such a nice post about your grandmother! We eat food to nourish ourselves, of course, and because it tastes good. But it’s also all about memories and love. Terrific post — thanks.

    Reply
    • Laura says

      June 7, 2019 at 3:55 pm

      Thank you, John! That’s so true – as with so many things, it’s about making memories that last even when our loved ones are gone.

      Reply

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