Usually I would follow this recipe from Duncan Hines®, but I got the idea of adding pudding mix from this version of the recipe, which is baked in a cast-iron skillet. I mean, adding pudding mix to cake batter can only make it better, right? ;) I also noticed that several people who reviewed these recipes noted that they replaced the water with pineapple juice (which my boyfriend also does), even though the recipe specifically says not to (I wonder why?). I figured, why not give it a shot?
So, here's what you'll need:
1/2 cup (1 stick) butter
1 cup brown sugar
1 (20 oz.) can pineapple rings (with juice)
Maraschino cherries (at least 6)
1 (18.25 oz.) box Duncan Hines® Moist Deluxe® Pineapple Supreme Cake Mix
1 (3.4 oz.) box vanilla pudding mix
4 large eggs
1 cup pineapple juice*
1/2 cup oil
*There should be just about enough pineapple juice in the can of pineapple rings, but you can add a little water to make up the difference without a problem if you need to.
First off, preheat the oven to 350°F. Place the stick of butter in a 13x9" cake pan and put it in the oven until it's completely melted. Sprinkle the brown sugar over the melted butter in the bottom of the cake pan, using the back of a spoon to smooth and spread the butter and sugar mixture evenly if needed. Next, arrange the pineapple slices on top of the sugar mixture. Eight whole ones will fit nicely, and the other two can be cut in half. Cut the cherries in half and place one in the middle of each pineapple ring with the cut-side up.
Now that the topping is arranged, it's time to mix up the cake batter. Combine the cake mix, instant pudding mix, eggs, pineapple juice, and oil in a large mixing bowl, beating it on low for about 30 seconds; it will be lumpy. Scrape the sides of the bowl and the paddle with a rubber spatula, then beat for about 2 minutes at medium speed. The batter should be nicely combined and no longer lumpy.
Pour the cake batter evenly over the brown sugar and fruit topping.
Bake at 350°F. I put mine in for 50 minutes as the recipe said, but I think it was a little overdone. I would recommend checking it after 40-45 minutes.
Let the cake cool in the pan for about 15 minutes on a wire rack, then carefully turn the cake out onto a serving plate. I find that the easiest way to do that is to place the plate on top of the cake while it's still in the pan, and hold the plate and pan together securely while flipping them. After flipping so that the serving plate is on the table, carefully lift the cake pan slowly to let the cake slide out onto the plate. That's all there is to it!
Serve slices of the pineapple upside down cake with whipped cream, and enjoy! Happy birthday, Dad! I love you. =)
If there isn't enough fruit for your liking, I'm sure you could add pineapple chunks or more cherry halves in between the pineapple rings. I know that my boyfriend prefers his pineapple upside down cake made with the pineapple chunks instead of slices; it isn't as pretty, but it's easier to eat and also to cut the cake into smaller pieces.