The first time my mom made this for the family...oh my goodness, we all thought we'd died and gone straight thru the pearly gates of heaven. It was the best thing we'd ever eaten. And, of course, my mom just beamed with pride. Don't know where she got the recipe, but it was divine, just the same. So buttery and caramely in addition to the deliciousness of the pineapple which we didn't get to have very often, back in the day. Mom always baked this in a 12" cast iron skillet - I have no idea how that little tiny woman was able to flip it over onto a plate.
Heat oven to 350°F. In 9-inch square or round pan, melt ¼ cup butter in oven. Sprinkle brown sugar evenly over melted butter. Arrange pineapple slices over brown sugar. Place cherry in center of each pineapple slice.
In medium bowl, beat remaining ingredients with electric mixer on low speed 30 seconds, scraping bowl constantly. Beat on high speed 3 minutes, scraping bowl occasionally. Pour batter over pineapple and cherries.
Bake 50 to 55 mins. or until toothpick inserted in center comes out clean. Immediately place heatproof serving plate upside down over pan; turn plate and pan over, together. Leave pan over cake a few minutes so brown sugar mixture can drizzle over cake and cake can release from baking pan; remove pan.