Boulevard's upside down pineapple cake

A homecooked version of the original from Boulevard Kitchen and Bar

This isn't your grandmother's pineapple upside down cake. Jason Pitschke, pastry chef at Boulevard Kitchen and Bar in Vancouver, reinvents the classic with cornmeal cake and pineapples braised in star anise, rum (Boulevard uses a maple smoked rum), coconut milk, ripe bananas and juices.

Braised pineapple

2 pineapples
3 pieces star anise
1/2 cup brown sugar
1/2 cup sugar
200 mL coconut milk
100 mL dark rum
3 over-ripe bananas
1 lime, zest and juice
90 mL water
90 mL passionfruit juice or orange juice concentrate
1 tsp salt

Preheat oven to 350 F 

Clean the pineapple, removing all the skin, and ensure you have all the “eyes” out, as these will be tough to eat even after cooking. 

Quarter the pineapple lengthwise.

Place pineapple quarters in a large enough braising dish with a lid if you have it. Otherwise, you can cover the top with tinfoil. 

Scattered star anise around the pineapple, then puree all the other ingredients together in a blender and pour over top of the pineapple. 

Seal with the lid or tinfoil and braise in the oven for 2 hours. 

Every 30mins, take the dish out of the oven and gently flip the pineapple so it cooks evenly. Spoon over top or baste the pineapple with some of the juices.

Cornmeal cake

3/4 cup sugar
3/4 cup butter
1 tbsp table salt
2½ whole eggs
2/3 cups all-purpose flour
2/3 cup yellow cornmeal
1 tsp baking powder
1 1/4 cup sour cream
1/2 tsp baking soda

In a stand mixer, cream sugar, butter and salt together. 

Slowly emulsify eggs alternating with flour mixed with cornmeal and baking powder. 

Fold mixture with sour cream. 

Sift in baking soda and mix for 1 minute until combined. 

*Note: this batter is best made the day before.


Preheat oven to 325 F. 

Use a nice round cake tin or a loaf pan (depending on your own preference). 

Take pineapple out of liquid and remove the core.

Cut slices of pineapple against the grain about 1/8 inch thick. 

Fan slices over the bottom of greased cake tin or loaf pan, at a slight angle, so the batter can bake in between and lock it in. 

Depending on the size of cake tin, it will determine how much pineapple you would use, but pack in as much as you can. 

Pipe the cornbread batter on top of the pineapple evenly and thinly coating the fruit. Less is more as the batter really puffs and envelopes the pineapple. 

Bake until nice golden brown colour is achieved, about 20-30 mins. 

Allow to cool on cooling rack. 

Place a plate or serving dish on top then flip it over onto the dish. 

Cut and serve with ice cream. Enjoy!