Pineapple Upside-Down Banana Bread

This stuff rocks. I cannot seem to get enough of it. It’s actually amazeballs. I mean, it’s amazing but better than amazing. In my parlance, this means it’s amazeballs. I think this is one of my all-time favorite creations. This is the second post inspired by my recent trip to Hawaii. (The first was a simple and traditional coconut pudding called haupia.)

On a Sunday evening in West Maui, we were fortunate enough to dine at a restaurant called Merriman’s, which is in Kapalua. It’s not a secret spot, the head chef Peter Merriman is one of the most famous chefs in Hawaii, and he reigns over an array of well-regarded Hawaiian eateries.

Bananas caramel caramel Wet ingredients

One of the desserts we had was a riff on the pineapple upside-down cake. Traditionally, the cake part of this is a simple yellow cake, often from a box of cake mix. And it’s not that great. It’s pretty blah, maybe kind of fun for a change, but not the sort of thing you’re going to crave on a regular basis.

Changing the boring cake mix into a superfly banana bread takes this dessert from ho-hum to holy amazeballs. Bananas and pineapple? And what about getting rid of the silly maraschino cherries and substituting in some macadamia nuts? And how about throwing a little rum into the pineapple syrup? Sign me up!

caramel banana batter pineapple pineapple upside-down banana bread

The banana bread that you use here makes a difference though. You want it to be a moist recipe, and you don’t want it to have too much chemical leavening, as you don’t really want it to dome up on top if you’re baking it in a cake pan. At Merriman’s they were individual sized cakes made in muffin tins where one wouldn’t have to worry about that, but here I wanted to make a full-sized cake.

The banana bread recipe that fit the bill is the Superfly Banana Bread from Carol Cotner Thompson. Carol is a cooking genius and Director of Culinary Education at the New School of Cooking in Culver City, California. I was fortunate enough to spend six months taking classes there and refining baking techniques. The banana bread recipe on her blog is really great, and it’s perfect for this use as well – just right for a 9×9 square cake pan.

pineapple upside-down banana bread

Pineapple Upside-Down Banana Bread
Prep time
Cook time
Total time
You will never think of either pineapple upside-down cake or banana bread in the same way. Get ready to have your world rocked.
Recipe type: Dessert
Serves: 9
For the topping:
  • 4 Tbsp. (2 oz. or ½ stick or 57 g) unsalted butter
  • ½ cup (119 g) dark brown sugar, lightly packed
  • 1 Tbsp. (15 ml) rum, light or dark
  • 2 Tbsp. (14 g) chopped macadamia nuts
  • 1 (20 oz or 567 g) can crushed pineapple in either syrup or juice, drained
For the banana bread:
  • 1.25 cups (160 g) flour
  • 1 cup (201 g) sugar
  • 1 tsp (5 ml) baking soda
  • ½ tsp (3 g) salt
  • 2 large or 3 small/medium ripe bananas
  • 2 eggs
  • ½ cup (118 ml) vegetable oil
  • ¼ cup buttermilk (this is optional)
  • 1 Tbsp (15 ml) pure vanilla extract
  • Butter and flour for greasing the pan.
  1. Preheat the oven to 350 degrees (177 C).
  2. Prepare a 9×9 (22×22 cm) cake pan by buttering it, dusting it with flour and tapping out the excess.
For the topping:
  1. Melt the butter in a nonstick skillet over medium heat. Add the brown sugar and the rum and cook until the sugar melts, stirring with a wooden spoon or a silicone spatula.
  2. Add the chopped nuts and stir just until coated with the caramel you just made.
  3. Kill the heat and pour the caramel/nut mixture into the prepared cake pan, spreading it out to the edges with your spoon or spatula. You’ll need to do this rather quickly, as the caramel will want to stop spreading as it rapidly cools.
  4. Evenly sprinkle the drained, crushed pineapple over the caramel/nut mixture in the pan.
For the banana bread:
  1. Combine the flour, sugar, salt and baking soda in a medium to large bowl. Whisk until well combined.
  2. In a separate bowl, mash the bananas well with a fork or a potato masher, then add the eggs, oil, buttermilk and vanilla extract. Mix well until you’ve got a homogenous mixture.
  3. Add the wet ingredients to the dry ingredients and stir until combined.
  4. Pour your banana bread batter on top of the pineapple/caramel in the pan and gently spread it to the edges.
  5. Bake for 30-35 minutes, until a toothpick inserted into the center comes out dry (a few crumbs are fine, you just don’t want it to be coated with wet batter).
  6. Immediately after removing the cake from the oven, invert the pan onto a cooling rack and remove the pan. Fix up the top of the cake with any bits that might have stuck to the pan, if needed.
  7. Let cool completely. Then transfer to a serving platter and enjoy!


IMG_1722pineapple upside-down banana bread

{ 4 comments… read them below or add one }

Mary Ann Sharp August 20, 2012 at 9:03 am

Hi Kyle, this sounds great I will print it out & see if mom wants to try it. I bet it goes good with a little ice cream or cream on top.


Kyle August 20, 2012 at 9:19 am

Pretty much anything goes well with a little ice cream on top! Or a lot of ice cream! :)


Margaret Steele September 27, 2012 at 10:33 am

Hi Kyle, Just wanted to wish you a very Happy Birthday! Your blog is wonderful. I haven’t tried the pineapple upside-down banana bread yet, but I intend to soon. It looks great…….sinful, but great. Muggs


Kyle September 27, 2012 at 3:45 pm

Thanks so much for the birthday wishes and the compliment on the site! It’s a lot of fun for me, and it’s nice that others enjoy it too. Definitely give the upside-down banana bread a try sometime — whenever I make it, it’s all I can think about the moment I get in the door is where is another piece of that cake! :)


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