Old-fashioned, made from scratch in a cast iron skillet, this is the real deal. Delicious! This is the only recipe I have ever used for pineapple upside-down cake because it's just that good and it's not complicated.
Gather all ingredients. Place oven rack in middle position and preheat oven to 350 degrees F.
Drain pineapple, reserving 2 tablespoons.
Melt butter over medium heat in 10 inch cast iron or nonstick skillet.
Add light brown sugar and stir until sugar is melted and begins to lightly bubble; remove from heat.
Place a pineapple slice on top of melted sugar in middle of pan, then place slices around it, overlapping slightly.
Place a pecan half in center of each ring, pressing lightly into melted sugar. Set aside.
Into mixing bowl, sift together flour, granulated sugar, baking soda and salt.
Add shortening and milk; beat 2 minutes at high speed with electric mixer (until smooth.)
Add egg and reserved 2 tablespoons pineapple juice; beat at high speed for additional 2 minutes.
Gently pour batter over pineapple slices in skillet and spread evenly.
Bake at 350 degrees F for 40-45 minutes, or until golden and cake springs back when gently touched in the center with finger.
Remove from oven and allow to cool on wire cooling rack for 5 minutes; run a knife or offset spatula around edge of cake to loosen from skillet.
Place serving platter over cake; hold skillet handle in one hand (with pot holder) and the platter in place with the other hand and turn upside down; shake the skillet gently, if necessary, to release cake onto platter. Lift skillet off and rearrange any pieces that may have been dislodged.
Lightly cover and refrigerate leftovers. Serve with whipped cream or vanilla ice cream if desired.