In this high-end take on the bake-sale favorite, pastry chef Eric Wolitzky of The Bakery at Cakes & Ale in Decatur, GA, ditches the dated maraschino cherries, swaps canned pineapple for fresh, and adds cardamom and top-shelf bourbon to bring out the flavor of the caramel. Pro tip: Let the cake cool for 30 minutes before inverting so the bourbon caramel can (deliciously) absorb.
Recipe information
Yield
8 to 12 Servings
Ingredients
Caramel
1
1
1
Cake
1
1
2
1
1
1
1
2
2
1
Special Equipment
Preparation
Caramel
Step 1
Preheat oven to 350°. Coat cake pan with nonstick spray; set aside. Cook brown sugar and butter in a small deep heavy saucepan over medium heat, whisking occasionally, until mixture is bubbling and sugar is completely dissolved. Boil, whisking occasionally, until caramel darkens, thickens, emulsifies, and pulls away from sides of pan, about 3 minutes.
Step 2
Remove from heat and whisk in bourbon (mixture will bubble vigorously). Return caramel to a boil; cook for 1 minute. Pour caramel into prepared cake pan and swirl pan until bottom is completely covered. Let cool completely before proceeding (caramel will harden).
Cake
Step 3
Cut skin from pineapple, making sure to remove all brown eyes. Cut 1/4-inch–1/3-inch-thick rounds from pineapple. Using cookie cutter, remove core to form rings. (If pineapple is very juicy, drain rings briefly on paper towels.) Arrange pineapple rings decoratively on top of caramel in cake pan without overlapping. (Cut rings into smaller pieces to fill any large gaps, if desired.)
Step 4
Whisk flour, baking powder, salt, and cardamom in a medium bowl. Using an electric mixer, beat sugar and butter in another medium bowl until light and fluffy, 5–6 minutes. Beat in vanilla. Add eggs one at a time, beating to blend between additions. Scrape down sides of bowl. Beat egg mixture until doubled in volume and very light and fluffy, about 2 minutes. Scrape bottom of bowl well, making sure to incorporate all butter into eggs. Beat for 1 minute longer.
Step 5
Beat in flour mixture in 3 additions, alternating with sour cream in 2 additions, beginning and ending with dry ingredients. Scrape batter into pan; smooth top.
Step 6
Bake cake until a tester inserted into the center comes out clean, 50–60 minutes. Transfer to a wire rack. Let cake cool in pan for 30 minutes. Run a sharp knife around sides of pan to loosen cake; tap bottom of pan and invert cake onto a large plate. DO AHEAD: Cake can be made 8 hours ahead. Cover with a cake dome and let stand at room temperature.
Nutrition Per Serving
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Reviews (203)
Back to TopIs it 1 1/3 cup of flour or just 1/3 cup ? The way the instructions are written Is confusing
Anonymous
5/27/2022
Love this cake! The saturation of the caramel into the cake is A++. And the fresh pineapple really adds a great texture here.
Anna
Birmingham. Al
4/11/2022
Excellent flavor, the brown sugar added a deeper flavor to the topping. I used golden rum in mine with good results and bourbon soaked cherries, although not the bright red or the other es they made the cake a more adult friendly. It received rave reviews from everyone, this is a keeper
Cincy Girl
Cincinnati Ohio
1/25/2022
Making this cake for Thanksgiving, since it’s a more manageable recipe than the one in this month’s issue (uses just about half the flour for example). Subbing cognac for the bourbon and also using gf flour. The house smells incredible!!
Amelia
Arlington, MA
11/24/2021
Oh, this cake was simply divine but quite a lot of work! I cheated a little bit and used Dole canned pineapple rings. I substituted 2% greek yogurt for the sour cream because I prefer the texture and flavor. I also "made" my own cake flour by using 14 TB of AP flour + 2 TB of corn starch for every 16 TB of cake flour in the recipe.
Caitlin Cuesta
Chicago
1/28/2021
Im obsessed with this recipe. Ive made it several times now. The only thing I do different is I add more cardamom, because Im a cardamom junkie. My only negative review is that my fruit "slides" down the sides as it bakes, so it doesn't stay center. Im sure there is a way to fix this but I haven't discovered it yet.
Anonymous
Indiana
1/4/2021
Finally--a really great pineapple upside down cake. I'm not usually a fan. Love cake. Love pineapple. Don't love them together. This, however, was fantastic! The crumb on this came was amazing. It's delicate and soft, but most and not crumbly. I can't wait to try this basic cake recipe for more types of cakes. I think the only thing I might do different with the pineapple cake is maybe a little less caramel. It's very sweet. I think it would be great with vanilla ice cream or some lightly sweetened whipped cream, though. So good!!!
toniakaye
Sevierville, TN
12/7/2020