Pineapple Upside Down Cheesecake, two layers of buttery pineapple upside-down cake stuffed with pineapple cheesecake, just like The Cheesecake Factory… but homemade!
Who knew your two favorite desserts could get any better, pineapple upside down cheesecake for the win.
Pineapple Upside Down Cheesecake
Oooooh boy… you know we love our cheesecakes. I have posted many a cheesecake recipe. But, normally it’s all about what Jeremy likes *eye roll*
…. but yesterday it was my birthday so it has been all about what I likes. So, I wanted a massive dessert for my birthday… is that a crime?!
My favorite cheesecake from The Cheesecake Factory of all time is their Pineapple Upside-Down Cheesecake. It’s a lightly flavored pineapple cheesecake layered between two buttery pineapple upside-down cakes.
It’s Heaven, basically.
So, for my epic birthday cake this year, I made this bad baby! It’s everything I hoped for! And then some. Cheesecake Factory cheesecakes are big… but this… this thing is ginormous!
This recipe, like my last cheesecake cake Strawberry Shortcake Cheesecake, takes a little planning ahead.
I suggest making the cheesecake the day ahead and letting it get nice and cold in the fridge overnight. BUT, the pineapple upside-down cakes should be made the day of for a nice presentation.
You can still eat it for days and days after but that first day it will look the best.
The recipe for the cheesecake is adapted from Allrecipes.com and for the pineapple upside-down cakes from Sally’s Baking Addiction (I’m obsessed with her, I know.)
This recipe contains affiliate links
Tools Needed to make Pineapple Upside Down Cake Cheesecake:
I have to be honest, I always get nervous after typing up a recipe like this. It looks like it’s totally complicated and will take forever but in reality, it’s not that bad.
Sure, this recipe probably isn’t for a complete beginner but just break it down into steps. Just look at the cheesecake recipe, then the topping, then the batter. See, not that bad.
I’m also being sensible with the portion sizes, believe me, a small slice of this goes a long way!!
Yummm, excuse me while I wipe the drool off my keyboard. This is one heck of a cake!!
I truly hope you liked today’s recipe! What is your favorite Cheesecake Factory cheesecake flavor??
How to make Pineapple Upside Down Cheesecake
Pineapple Upside Down Cheesecake
Ingredients
Pineapple Cheesecake
- 4 8 oz packages cream cheese room temp
- 1 1/2 Cups granulated sugar
- 3/4 Cup milk
- 4 eggs
- 1 Cup sour cream
- 1 Tablespoon vanilla bean paste or extract
- 1/4 Cup all purpose flour
- 1/3 Cup pineapple juice
Pineapple Upside-Down Cake Topping
- 1/2 Cup unsalted butter melted
- 1 Cup packed light brown sugar
- 12 slices canned or fresh pineapple rings
- 12 maraschino cherries
Pineapple Upside-Down Cake Batter
- 3 1/3 Cup all purpose flour sifted
- 1 teaspoon baking powder
- 1/2 teaspoon baking soda
- 1 teaspoon salt
- 1 Cup unsalted butter melted
- 1 1/2 Cup light brown sugar packed
- 1/2 Cup granulated sugar
- 2 eggs
- 1/2 Cup sour cream
- 1 Cup milk
- 1/2 Cup pineapple juice
- 2 Tablespoon vanilla bean paste or extract
Instructions
Pineapple Cheesecake
- Preheat oven to 350 degrees. Grease a 9-inch springform pan. Cream the cream cheese with the sugar until smooth in a large bowl. Mix in the milk fully then add in one egg at a time and mix. Add in the remaining ingredients and mix until smooth with no lumps.
- Pour into the pan and bake for 1 hour, the center will be slightly jiggly. Shut off oven and let cool down in the oven for 5 hours. Top with plastic wrap and place in fridge overnight to get cold.
Pineapple Upside-Down Cake
- Start with the topping by dividing the melted butter equally between two 9 inch cake pans. Sprinkle 1/2 Cup of the brown sugar into each pan. Arrange the pineapple slices and cherries as pictured, set aside.
- Preparing and cooking the cake: Preheat oven to 350 degrees. In a large bowl, add in the sifted flour, baking powder, baking soda, and salt, whisk to combine.
- In a medium-sized bowl, add in the 1 Cup melted butter, brown sugar, and granulated sugar. Whisk to combine, getting all the brown sugar lumps broken up. Whisk in the eggs, sour cream, milk, pineapple juice and vanilla until combined.
- Add the wet mixture to the dry mixtures and mix until combined, with no dry spots or lumps.
- Evenly divide the batter between the two pans, about 2/3 of the way full, do not overfill!
- Line oven with foil or two cookie sheets, cakes may bubble over some. Bake for 48-53 minutes, covering loosely with foil at the 20-minute mark to avoid burning. Cakes are down when a toothpick inserted in the middle comes out clean.
- Place cakes on a wired rack to cool for 10 minutes.
Pineapple Upside-Down Cheesecake Assembly
- Invert cakes, one onto a flat surface like a cutting board and the other on the plate you will be presenting on.
- Take out the pineapple cheesecake. Trim top of the cheesecake if it is not even. Take it out of the pan and lift it off the bottom carefully, you may need to use a tool like a frosting spatula to help. Place on top of the first cake layer. Trim the sides of the cheesecake with a knife if necessary. Place the second layer of cake on top. Serve as is or with whipped cream, enjoy!!
Nutrition
Dana DeVolk
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Katherines Corner says
May 21, 2015 at 2:02 pmThank you for sharing at the Thursday Favorite Things blog hop. I featured you on facebook and google plus and pinned to my Just desserts board. xo
Jenna says
May 22, 2015 at 2:46 pmOh my goodness! This looks sinfully delicious
Laurie says
May 26, 2015 at 2:38 pmOhhhhh! Do I ever want a slice of this! Thank you so much for sharing with us at the Brag About It Link party!
[email protected] Charm says
May 31, 2015 at 10:16 pmThanks so much for sharing this yummy recipe at my Show and Share party…it will be featured at this weeks party.
Blessings,
Linda
edy says
February 3, 2016 at 1:09 pmjust perfection made cake! congratulations!!
Trina says
February 5, 2016 at 11:00 amHi! Is there a way to bypass letting it cool down in the oven for 5 hours?
Dana DeVolk says
February 5, 2016 at 5:46 pmI honestly don’t know, I have only made it this way. If you try another way and it works, I would love to know, thanks!
Natalie says
March 26, 2016 at 5:27 pmHi!!
I’m attempting to make this right now actually. Do you know if you can bake both the cheesecake as well as the cake the night before and assemble the next day?
Dana DeVolk says
March 26, 2016 at 6:00 pmWhen I made this I made the cheesecake the day before, then let the pineapple cakes cool completely. It should be fine to make them both ahead of time! I hope you love it, it was soooo good!
Rubyt says
March 31, 2016 at 5:15 pmDo you also add the pineapple to the bottom cake layer just like you do on the top layer?
Dana DeVolk says
March 31, 2016 at 6:14 pmYes!
JULIE says
April 1, 2016 at 3:29 pmSo just made the Pineapple upside down cake, looks good, smells good. Can’t wait for his party tonight. He loves Pineapple upside down cake and Cheesecake. So this should be a win, win situation. The only thing I did different is I made some homemade caramel rum topping to drizzle on the pieces after sliced if they want it. I know gilding the lily here but sounded good?
Lisa says
January 20, 2017 at 10:12 pmMy son saw this on facebook and tagged me in it. He loves pineapple upside down cake so this is over the top.
making it tonight for his 30th birthday. praying my cheesecake turns out. fingers crossed. Thanks for the recipe.
April says
March 1, 2017 at 4:01 pmDo I need to do a water bath or wrap foil around the spring form pan?
Dana DeVolk says
March 1, 2017 at 4:25 pmNope!
April says
March 1, 2017 at 5:47 pmThanks. I’m making this for my husbands birthday tomorrow. I just don’t want to mess it up.
Monica Padilla says
April 4, 2017 at 12:02 amWas the cake supposed to be dense? It was kinda like fruit cake. Still very good and everybody loved it but I’ve never had pineapple upside down cake that wasn’t fluffy. Maybe I’m just used to box cake mix for them
Nadine says
June 24, 2017 at 3:10 pmthis turned out amazing! one question, does it make a difference to assemble and then refrigerate until dinner time??
Dana DeVolk says
June 24, 2017 at 3:16 pmYay! I’m so glad it turned out good. I think refrigerating for a while before cutting in will definitely help. If the cheesecake layer gets warm it might get kind of soft and mushy.
Jannarama says
July 26, 2017 at 2:05 amThis is my favorite flavor at The Cheesecake Factory…actually, I should’ve said, WAS. I found out a month ago it’s no longer on the menu. I was heartbroken. Thank you for your recipe.
Mayra says
November 3, 2017 at 3:16 amIm making IT right now
Hope I can Do it!!!!????
Dana DeVolk says
November 3, 2017 at 8:10 amYes, you can!
Pd says
November 21, 2017 at 12:13 pmCan I use a box cake mix?
Dana DeVolk says
November 21, 2017 at 12:45 pmYes, you can!
Kristen says
January 13, 2018 at 10:07 amDo you know if you can do half the amount for the cheesecake so it is a thinner later in the middle?
Dana DeVolk says
January 13, 2018 at 2:17 pmI have never tried, but I think it would work. I’m not sure how long it would need to bake for though. If you do this, please let us know how it comes out!
Valerie says
June 25, 2018 at 1:21 pmI just finished the cakes. I made the cheese portion 2 days ago and
Refrigerated it. The top was nice golden brown and it was set.
My question is the cheesecake part is soft and not solid like a NY cheese. Is that the way it should look? I followed all instructions to the letter.
Brittney Causey says
August 13, 2018 at 11:22 pmI made this cake last night! I had to come write a review because I love baking, but I haven’t had all the experience in the world because I’m only 20, haha. So with that being said I’ve never made a pineapple upside down cake OR a cheesecake. But it came out so well. Yes it tests your patience but if you follow the instructions you’ll be happy you did. I’ve always been one to rush putting icing on a cake and then it melts. So I was very impressed that the cheesecake turned out well for my first time. The cakes are dense, but I think it’s better that way because I used canned pineapple and it’s almost like a buttery, caramelized pinapple sweetness absorbed through the cakes and they were definitely not dry. They also were NOT soggy and falling apart in any way or even crumby. When I assembled the layers I just looked at it in awe because I was almost certain I would’ve messed it up. So Thank you for this recipe! I posted it on my Facebook and everyone seemed jealous 🙂
Dana DeVolk says
August 14, 2018 at 8:25 amThank you so much for your thorough review Brittney! I agree, the cakes are a bit dense but they need to be in this instance. I’m so glad you liked the recipe!!
Sarina says
October 30, 2018 at 1:38 pmI cannot find the recipe itself…i can see the comments and the pictures but no recipe. Please help! I would love to make this cake for my dads birthday…this was his favorite flavor at Cheesecake factory! Thank you!
Dana DeVolk says
October 30, 2018 at 5:39 pmThe recipe is at the bottom of the post right before the comments. It is blocked off in a printable recipe card. Thanks!