Melt butter and pour into a pan. Spread evenly. Sprinkle brown sugar over top. Place the pineapple in rows in the pan with a cherry in the middle of each. Set aside.
Whisk together flour, baking soda, and salt, set aside. In a stand mixer, beat the butter on medium high speed until fluffy. Add sugar. Beat until incorporated.
Add eggs one at a time. Add vanilla and sour cream. Working in two batches, add half flour mixture and half the milk. Mix and repeat with remaining ingredients.
Pour over pan, spread evenly. Bake at 350°F for 45 minutes. The 'top' of the cake will brown slightly. Let cool 20 to 30 minutes before serving.