My Mom's Pineapple Upside-Down Cake

Author Notes

My mother was a good cook, and made many memorable dishes. But when I try to think of just one that typifies what she taught me about cooking, it's hands-down this cake. It's a cake that invites another bite, another slice. My Mom taught me to bake it when I was in junior high school, and it tastes just as delicious today as it did all those years ago. You must bake this in a black cast iron skillet, and I still have the skillet my Mom baked this cake in for as long as I can remember. She's been gone for a very long time now, about 25 years (forgive me for not having a photo of her to upload), but her cake lives on and always bring tears of joy to my eyes. —Abra Bennett

Test Kitchen Notes

When reading up on the origins of the pineapple upside-down cake, I came across the connotation, instead, of an upside-down pineapple. It's probably inappropriate to get into the details of that here, so consider this an internet scavenger hunt gift.

Anyway...back to the cake at hand. Pineapple upside-down cakes—or really, any cake designed top-to-bottom, with the intention of being flipped right-side-up—have always held a special place in my jigsaw-puzzle-loving heart: There's something very sweet, very 1937-technicolor Snow White, about lovingly draping slices of neon fruit into a pan. This recipe from (two-time contest winner!) Abra Bennett is no exception. Sugar and butter bubble together to form a simple caramel that floods the bottom of the cake pan. Pineapple rings and clawlike pecans nestle into that buttery sugar, and get topped with billowy, eggy cake batter. As the cake bakes, the molten sugar shellacs the fruit and nuts, creating a stained-glass effect. As the batter lifts and puffs valiantly, it soaks in all those caramelized pineapple juices. (Cue the whistling woodland creatures here.)

After 45 minutes in the oven, the cake will be cooked through and the fruit tender and burnished. Don’t skip the 30-minute rest in the pan, which will help firm everything up for the big event: the flip. Cover the rested cake with a large enough plate and flip confidently and quickly (feigned confidence will sub in just fine here). Admire your work—if a pineapple ring or pecan has fallen out, just nudge it back into place. Cut into wedges, tame with dollops of unsweetened soft-whipped cream, and eat as you think about Abra Bennett cheekily eating the entire cake by herself. —Coral Lee