Pineapple Upside Down Cake

Simply the best version of this classic recipe: Pineapple Upside Down Cake

Pineapple Upside Down Cake

A friend of mine was coming over to our house for a visit with her boyfriend (who happened to be having a birthday).  She asked if I might be willing to whip up a pineapple upside down cake for the occasion as her boyfriend was crazy about this variety.  Since I didn’t already have this cake on the website, I was happy to take on the challenge.  I baked it once and it wasn’t quite perfect enough.  I made some minor changes, baked it again, and it was absolutely perfect.  In fact, it was so perfect that I’ve made this recipe three times since.  It’s GOOD!

Pineapple Upside Down Cake Recipe

The best part is when you flip it over onto a serving plate while it’s still warm.  The pineapple transfers and sits on top of the cake with lots of sugary juices.  It’s really tough not to dig in right then and there while it’s still warm- which is perfectly okay, by the way!

Pineapple Upside Down Cake Recipe -

It’s a bright and sunshiny kind of cake, which is kind of nice this time of year!  And the boyfriend mentioned above… he was very pleasantly surprised, and he loved his birthday cake.

Pineapple Upside Down Cake

Yield: 8 servings

Prep Time:25 minutes

Cook Time:40 minutes

  • 3/4 cup + 2 tablespoons light brown sugar, divided
  • 1/4 cup (1/2 stick) unsalted butter, melted
  • 6 canned pineapple slices + 6 maraschino cherries
  • 1/2 cup sour cream, divided
  • 2 large eggs
  • 1 tablespoon pineapple juice (from the can)
  • 1 teaspoon vanilla extract
  • 1 1/4 cups all-purpose flour
  • 3/4 cup granulated white sugar
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup (1 stick) unsalted butter, softened
  1.   Preheat the oven to 350 degrees F.  Spray an 8-inch round pan with nonstick spray (or rub with a little bit of butter).  Sprinkle the bottom of the pan with 2 tablespoons of brown sugar.
  2. In a small bowl, whisk together 3/4 cup brown sugar with the melted butter.  Arrange pineapple slices into the bottom of your prepared pan (5 around the edges and 1 in the middle... snuggle them in there).  Place a cherry in the middle of each pineapple slice.  Spoon the butter/sugar mixture over the pineapple slices.  In a small bowl, whisk together 1/4 cup sour cream, eggs, pineapple juice and vanilla.  Set aside.
  3. In a large bowl, whisk together the flour, sugar, baking powder, baking soda and salt.  Add the remaining 1/4 cup sour cream and the softened butter to the bowl, and use an electric mixer to incorporate it into the dry ingredients until smooth.  Bump up the speed to medium and beat until fluffy.  Add the egg mixture and beat again until the batter is smooth- about 2 minutes.
  4. Spread the batter evenly over the pineapple slices.  Bake 40 minutes (or until golden).  Cool for 5 minutes, then place a serving plate on top of the pan and carefully turn over and coax the cake out of the pan and onto the serving plate.  If any of the pineapple sticks to the pan, just pull it out of the pan and put it in its place on the cake.  Drizzle any remaining pan juices over the cake.  Let cool, then slice and serve.

More upside down cake recipes you might enjoy:

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  • Chanel Johnson wrote:

    Good things take effort and time…. I’m sorry and everyone is entitled to their recipe…. But I have made this recipe several…. SEVERAL times (using fresh Pineapple though) and it maybe easier but a Duncan Hines or any box… tastes wise falls extremely short of this here. Very. VERY good.

    And yes in a pinch I am not prejudice diced against Duncan Hines. I keep ole DH stocked in my pantry for sure and those ‘pinchy’ times. And if I must use a box it is the only one I pull.

    However, a box cake— especially Vanilla ‘based’ and flavors due to the high… artificial flavor they have to use to even resemble…the true taste of ‘Vanilla, Lemons, Pineapple, Cherry and even White Cakes… etc. does not taste ‘ just as good’. Chocolates maybe…MAYBE–the only closest in taste. MAYBE. In the others…. I can definitely tell in not only texture but ABSOLUTELY… in taste…the artificial taste is detectable… Not necessarily bad…but detectable.

    Anyway, back to this cake here. Delicious. Delicate moist in the actual cake itself and with fresh Pineapple….one of out of 3 recipes I (currently) only use.

    Faster to put together yes…. Taste definitely… NO!

  • Laura @ Laura’s Culinary Adventures wrote:

    I haven’t had a pineapple upside down cake in forever! So fun!

  • Kari wrote:

    This is a childhood favorite of mine! I always wanted more cherries though!

  • Nicole wrote:

    Gotta love the classics! This is one of my childhood favorites!

  • Rodney wrote:

    I only had pineapple tidbits when making one time. Used them with chopped up cherries. Spread all over bottom of pan. Made for very nice flavoring in each bite. Much simpler than trying to get a bit of rings and cherries in each bite. I have used tidbits ever since.

  • Lorna wrote:

    Ah, this reminds me of tea at my grandparents with squirty cream and 1960s crockery.
    Absolutely not a bad thing.

  • Annamaria @ Bakewell Junction wrote:

    My cousin loves this cake.  I’ll have to make it for her soon.

  • Diana Hawes wrote:

    Hi, I love this recipe but I have a MUCH easier one and I think just as good. A box of Duncan Hines Pineapple Cake Mix. For the liquid I use the juice from the can of pineapple rings. And of course the rest of the ingredients that is called for.

  • Kristen wrote:

    One of my favorites – especially warm!!