This was the Valentine's Day dessert I made for Kurt. He gets random pineapple upside-down cake cravings and then pesters me about it for months until I make him one. This time he started wanting cake several weeks before Valentine's Day so I just put it off until then so I could combine request fulfillment and obligatory Valentine's Day sugar into one neat little package.
Preheat the oven to 350 degrees. Put some butter in a 9-inch pan (square and round are both fine) and put it in the oven to melt.
Meanwhile. Add really really soft butter or shortening to your bowl. Since you're going to basically be whipping the batter instead of stirring it, it's just much easier if it's entirely softened. (BTW, I used my kitchenaid mixer with the wire whip for this but a hand mixer would also work just fine. Just DON'T think it will turn out as well if you just stir the ingredients up. It needs to be fluffy.)
Add flour, sugar, baking powder, and salt. Also milk and egg which are not pictured but I trust you to figure it out. Mix it up on low speed for 30 seconds or so - enough to get it all stirred together so flour isn't flying everywhere.
Meanwhile, take the now-melted butter out of the oven, make sure it's spread evenly around the dish, and add a layer of brown sugar. The recipe said 2/3 cup, but I don't measure. As long as it's a nice thick layer. (Warning: butter and brown sugar are so delicious together you will want to eat this as is. Resist.)
Ok everything's pretty much stirred together now. Turn your mixer up to high.
Let it run for several minutes until the batter is really fluffy.
Now arrange your pineapple rings in an adorable flower. Or a boring square if you're using a square pan. A can of pineapple rings has exactly nine rings I believe so it's just enough to fill up a square pan. So convenient.
Maraschino cherries! Some people like to just put one in the middle of each pineapple ring which I will admit is probably cuter and more orderly but you don't get as many cherries that way so my way is better.
The batter should be looking nice and fluffy by now.
Spread it over the top of your pineapple and bake. It goes for almost an hour so it's good to get it in the oven and then make the rest of dinner.
When it comes out, let it sit in the pan for a couple minutes. If you don't, all the sugar and butter in the bottom (top?) will be completely liquid so it will get everywhere instead of staying on the cake where it belongs. I flipped one of these over too soon once and it was a truly sad day for me. But also don't let it sit for too long or it will stick to the pan and be gross.
Flip it over onto a plate, NOT a cooling rack. That way you don't lose any sugar and butter. Very important.
This is so good, you guys. And I don't even usually like cake.
I used this recipe from Betty Crocker. (I used butter instead of shortening because I don't keep shortening in the house but other than that I didn't make changes.