We've come up with a delicious mashup of two nostalgic favorites that will be sure to garner plenty of oohs and ahhs once it's tipped out of the pan. In addition to lining the bottom of the pan with pineapple, we mix piece of the fruit into the buttery batter for double the flavor. Baking ahead works beautifully for this dessert, which gets even better after resting a bit so the caramelized sugar and pineapple juice absorb into the cake.
Butter all sides of a 9-by-5-inch nonstick loaf pan, then pour the melted butter into the bottom of the pan. Scatter the dark brown sugar evenly over the melted butter. Arrange 7 slices of pineapple and the maraschino cherries in your preferred design along the bottom and up the sides of the pan, halving the slices as necessary. Place the pan in the refrigerator to chill while the batter is prepared. (This will allow the fruit to set in the butter and minimize shifting when the batter is poured into the pan.)
Cream the granulated sugar, lemon zest and 2 sticks room-temperature butter in the bowl of a stand mixer fitted with a paddle attachment on medium-high speed, scraping the bowl down halfway through, until pale and fluffy, about 6 minutes.
Meanwhile, whisk together the flour, baking powder and salt in a medium bowl and set aside.
With the mixer on medium high, add the eggs and egg yolk in 1 at a time, making sure they are fully incorporated between each addition. Reduce the speed to medium-low and add the vanilla and 1/4 cup sour cream; mix until incorporated. Add half of the dry ingredients and mix until just incorporated, then repeat the steps with the remaining sour cream and dry ingredients, making sure to scrape the bowl down between each addition. Add the chopped pineapple and mix until just incorporated, about 15 seconds.
Remove the prepared loaf pan from the refrigerator and carefully pour in the batter, being careful not to shift the assembled fruit. Using a small offset spatula, carefully spread the batter into the corners and smooth out the top. Give the pan 5 to 10 taps on the counter to release any large air pockets.
Place a sheet pan on the bottom oven rack and bake the cake on the middle rack until the top is deep golden brown and a cake tester or knife inserted in the center comes out clean, 1 hour 20 minutes to 1 hour 25 minutes. Allow the cake to rest for 30 minutes before inverting onto a serving plate.
When measuring flour, we spoon it into a dry measuring cup and level off excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.)
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