A much as I love the taste of fresh pineapple, there are times when only canned will do. The best example of this is pineapple upside-down cake, which was specifically designed to showcase the wonders of fruit in a can. America had been industrially processing the exotic fruit since the end of the Civil War, but its popularity exploded in the post-WWI era thanks to improved machinery, increased supply, and affordable pricing. The original recipe for upside-down cake called for canned pineapple, jarred maraschino cherries, butter, and brown sugar to be baked underneath a scratch-made vanilla cake batter; by the 1950s, the homemade batter had been replaced by a boxed cake mix. A true pineapple upside-down cake is a monument to modern times, singing the praises of processed foods. So why not create a cocktail that does the same?
This playful pineapple upside-down beverage, while not a cake, stays true to its roots by embracing the convenience of canned pineapple. It isn’t “settling” for inferior fruit—it’s celebrating it. And, just like its baked counterpart, it requires no special skills or know-how. It’s sweet, easy, and amazing, which is everything canned pineapple ought to be.
- 1 (8-oz.) can sliced pineapple
- 2 Tbsp. butter
- 1/4 cup light brown sugar, plus an extra 1/4 cup or so
- 1/8 tsp. vanilla extract
- Pinch of kosher salt
- Maraschino cherries
- Dry sparkling wine, or a non-alcoholic alternative
Drain the pineapple rings, reserving the juice and the can. In a small saucepan or microwave-safe bowl, melt the butter with a tablespoon of the pineapple juice, then stir in the 1/4 cup brown sugar and continue heating just until the sugar melts (about 30 seconds). Stir in the vanilla and salt; if the sauce isn’t smooth, drizzle in a bit more of the pineapple juice while stirring until it comes together. Cut the pineapple rings in half, put them back in the can, pour in just enough sauce to cover, and let it sit for about 5 minutes.
Place the pineapple slices on a plate lined with wax paper or parchment paper. Pour the sauce from the can into a bowl with the remaining sauce from the saucepan, and the remainder of the pineapple juice. Sprinkle a bit of brown sugar on top of each pineapple slice, gently pressing down to coat, then freeze for at least 15 minutes.
Rim two highball glasses with pineapple sauce and brown sugar. Divide the frozen pineapple slices between the two glasses, then add a maraschino cherry or two (or however many you like). Fill the glass with sparkling wine, let it sit for about 20 seconds, then give it a taste. Add a little bit more of the sauce as desired. Otherwise, enjoy your cocktail, and drink the sauce separately later.