Let’s just say it’s all the deliciousness of upside-down cake, and none of the fuss. 
Credit: Getty / Daniel Mazilu / 500px

Pineapples always feel like something of a mystery. That spiky forbidding exterior, myriad myths about how to determine ripeness, the complexity of prepping it for eating without injury to self or fruit. But there is just nothing like the heady, floral intensity of a great pineapple to keep us coming back. One of my favorite desserts that features pineapple is a classic upside-down cake. Those rings of fruit, caramelized and supple yet still juicy and fresh, they are a deep pleasure. Such a deep pleasure I wondered if I could mimic it without all the cake business. Turns out, you can. 

My new discovery: roasted pineapple!

Here's the thing: By forgetting the cake part, and merely by roasting pineapples whole with a bit of sugar, you get all the wonderful texture and flavor benefits, but you also end up with a dessert that is simpler and lighter. Further, this technique is a great way to salvage a pineapple that is slightly underripe, or to amplify the sweetness of a perfect one. And you can make several of them at once, so it is a fun dessert option for a crowd.

Once you have a roasted pineapple you can find all sorts of ways to serve it:

  • Keep it simple with a few slices and garnish with toasted slivered almonds or flakes of coconut
  • Serve alongside a scoop of mango sorbet or coconut ice cream
  • Create a fancy layered dessert with crumbled pound cake and vanilla custard

How to roast pineapple

For starters, choose your whole pineapple. At the supermarket, look for fruits that feel heavy for their size and are more yellow than green, and smell fragrantly sweet on the bottom. If they smell at all like booze, they are past their prime. 

To prep, cut of the top and bottom of the pineapple and set it upright on your cutting board. Cut the peel off in wide strips from top to bottom. If you have missed any "eyes," go back and remove them with the tip of a paring knife, as they are unpleasantly tough to eat. Pat dry on the outside with lint-free paper towels.

Here's all you do:

1. Heat your oven to 350° and get a large, oven-safe, nonstick skillet out.

2. For each pineapple you need 1 tablespoon of light brown sugar and ½ tablespoon of neutral oil (I often use either avocado oil or coconut oil for this).

3. Heat the oil in the pan and add the pineapple. You can usually get two whole pineapples in a pan, and I find it is always worth making them two at a time. Turn the pineapple every couple of minutes to get a good caramelization all over.

4. Once the pineapple is a bit browned, sprinkle the sugar over them, and give one more full turn to coat. Then transfer to your oven and roast until hot all the way through and tender, about 20-25 minutes. 

5. Remove from the oven, transfer to a shallow baking dish and pour the caramel over. Let rest 5-10 minutes before serving if you are serving warm. These will keep well in the fridge up to four days and can be reheated.

6. Slice and garnish as desired for serving.