Pineapple Upside Down Cake for 150

Note: Recipe has been updated on February 11, 2009 to clarify some instructions and correct a typo.

When we moved to the country, we decided to join the local Volunteer Fire and Rescue Company. It took us a while to actually do it, but both Keith & I became members early this year. My role is strictly support and fund raising. For instance, I build our web site, I help with putting together flyers, brochures, with setting up fund-raiser dinners, breakfast, bake sales etc. Those activities are more critical than ever this year, as we are buying a much needed new fire tanker. Joining a volunteer fire company is a sure way to become more engaged in a new community and it allows you to give your time and your skills to your local community in a way that makes a difference: we help neighbors in emergencies.

This past week-end, WVFR offered an-all you can eat ham & oyster dinner as part of its continued efforts to raise money for our new tanker fund. I was working that night, cooking a 5-course dinner for 11 on a lovely hilltop house, I would not be able to participate. So I said I would bake one of my specialties: a pineapple upside-down cake.

I have a soft spot for upside-down cakes (something easily verifiable by looking at the list of cake recipes I posted so far); I love pineapple, one of the fruit growing at my childhood home; and I love the uncomplicated unsophisticated sheer goodness of a good pineapple upside down cake. Don’t get me wrong, I have eaten my share of unpalatable ones – generally too dry. But this cake is moist and flavorful.

I have found that it’s a popular cake at gathering (I rarely have any left over to take home); people of a certain age (over 40) reminiscence fondly about it (how their mom used to make one for their birthdays for example), and yet – not many people make it today. You can be pretty sure to see multiple plates of brownies at a pot-luck, but I have never seen another pineapple upside-down cake (as a matter of fact, a young 18-year old at that dinner had never seen one). It does take a little time to make, but really, not that much. Is this the butter in it that people are afraid of? Is this that there were too many poor versions that were made? For me, it’s one of those ideal, comforting, utterly delicious and homey cake that can be made in advance and is good at any time of the day, like a real homemade pound cake, as a matter of fact. And it’s so good for breakfast with a cup of strong coffee made stove-top in the percolator.

So, on Friday late morning, after picking up some farm eggs, flour, maraschino cherries and good milk at one of the local country stores, I arrived at the fire hall to use the kitchen and make lots of it. The day before, our Treasurer, our Chief and I had gone bulk-shopping for 200 in Winchester, but Costco simply did not have some of the items I needed – or had them in quantities that were simply too large for my purpose. So I stopped at Roy’s in Sperryville to round up what I needed.

The original recipe was printed in Saveur Magazine in December 1998, almost 10 years ago. I have saved all my issues of Saveur and often go back to them, but I have a particular fondness for the article accompanying the recipe: it was titled “The Convent Cook – Maria Tisdall rescued herself from restaurant hell – and answered the prayer of 65 nuns.” And it was the story of how this match made in heaven between Maria and the Benedictine sisters at Saint Walburgha monastery in New Jersey came to be. Only one recipe was published: the Pineapple Upside-Down Cake. The ingredients were for an 8” x 8” cake, but the picture showed a cake easily twice as big, as it displayed 20 pineapple rings. When I first made the recipe 10 years ago, I was fooled (thinking I was making a large cake) – and somewhat ticked when it was a small cake! Frankly, an 8” x 8” cake is grossly insufficient: it’s gone too fast. I always at least doubled the recipe, sometime tripling it. So in the end, I rewrote the recipe, making made some substitutions, omitting the almond extract and adding some of the pineapple juice and maraschino liquid to the topping – along with a few “tricks” of mine. The cake is rich, so a little goes a long way, but it keeps for several days in the fridge), and it freezes beautifully (cut it into individual portions first.)

And so Friday afternoon, I made four 19” x 13” cakes, each with 24 whole pineapple slices, for a total of 96 large squares. Because we had a lot of food and other desserts, I halved most of the portions in much more manageable size for dessert after such a large dinner. They were all eaten: nothing was left.

As usual, I urge you to buy the best ingredients you can afford. Specifically the quality of the eggs and butter make a huge difference!

Pineapple Upside Down Cake

Note: Recipe has been updated on February 11 to clarify some instructions and correct a typo.

Make a 19” x 13” cake or 24 large squares

Ingredients:

• 2 tablespoons canola oil to grease the pan
• 24 tablespoons (i.e. 3 sticks) of unsalted butter (not margarine), soften to room temperature, and divided into 2 stick & 2 tablespoons (i.e. 18 T) for the caramel/topping and 6 T for the batter
  
• 3 cups brown sugar
• 24 pineapple rings – about 3 15-oz can pineapple rings in juice (not in syrup) (you may have a few rings left)
  
• 1 8z jar maraschino cherries, pitted and stemmed
• 1 cup + 2 Tablespoons of whole milk
• ¾ cup canola oil
• 2 teaspoons strong vanilla extract
• 3 cups + 6 tablespoon of all purpose flour (I have used whole white wheat in the past and it’s perfectly acceptable)
• 4 teaspoons baking powder
• 1 ½ teaspoon salt
• 2 ¼ cup sugar
• 6 eggs

Instructions:

1. Turn oven on to a temperature of 350 F
2. Oil the pan with a pastry brush (or your fingers) using up to 3 tablespoons of the canola oil. Make sure to get the corners and sides well. Do not be stingy as you want the cake to unmold easily. Roughly chop 18 tablespoons of butter (2 sticks + 2 tablespoons) and scatter at the bottom of pan. Put pan in oven while it’s preheating. Keep an eye on it, and take it out of the oven as soon as butter is melted. It should do so before the oven reaches 350 F. Put the remaining 6 tablespoons of butter in a very large bowl on the stove where it’s warm to help it soften.
3. Sprinkle the bottom of the pan with the brown sugar evenly, again making sure to reach all sides and corner. Lift the pineapple slices from the juice (reserve the juice) and arrange them in a grid pattern. Sprinkle 6 tablespoons of the pineapple juice over. Reserve the rest for another use (it’s perfectly good to drink, you know). Sprinkle two tablespoons of maraschino liquid from the jar over the pineapple. You could push one cherry in the center of each ring now, if you want, but they’ll look better if you do this after the cake has been baked.
4. In a bowl, combine milk, the 3/4 cup canola oil and vanilla. In another bowl, sift together flour, baking poweder and salt.
5. In the very large bowl where you set it to soften, beat together the remaining 6 tablespoons of butter (which should be very soft by now) and the sugar until light and pale lemon colored. It will look “mealy”. Beat in the eggs, one by one, then add the milk mixture, and the flour mixture (1 cup at a time) beating well after each addition. Pour batter over the pineapple rings, smoothing it out as necessary. It may looks like there is no enough batter: there is!
6. Bake in the preheated oven until cake is golden and a toothpick or skewer comes out clean, 1 hour to 1 hour and 10 minutes. Remove from oven, let cool until you feel comfortable handling the pan.
7. Now comes the tricky part: inverting the cake. Position the cake inside a rimmed cookie sheet (rim facing up). Put another rimmed cookie sheet on top of the cake (rim facing down). The cake is now sandwiched between two rimmed cookie sheet. Clamp the two cookie sheets together and invert the cake quickly and decisively but carefully. Remove the pan from the cake carefully. If necessary, use a spatula to remove any stuck ring and put it back on the cake. Scrape any caramel from the pan and put it on the cake.
8. Push one cherry in the center of each ring.
9. Let cool and cut into square s, one for each ring.

Voila! Not too bad for such a delicious comforting cake!

Locavore log: eggs, milk, butter – that’s it, I am afraid…

For the Recipe ONLY, in printable form, click: HERE

Individual Pineapple Upside Down Cake

Update Dec 2008: following several questions on individual cakes and substitutes for Maraschino cherries, here is a picture on an individual cake using dry cranberries. Cute, no?