OLD SCHOOL PINEAPPLE UPSIDE DOWN CAKE
Ingredients
For the Topping:

¼ cup unsalted butter melted
½ cup light brown sugar
1 20-ounce can pineapple slices drained
Maraschino cherries stems removed

For the Cake:
1 ½ cups all-purpose flour
1 ½ tsp baking powder
½ tsp kosher salt
½ cup unsalted butter (1 stick) room temperature
¾ cup granulated sugar
2 large eggs room temperature
2 tsp vanilla extract
⅓ cup sour cream room temperature
⅓ cup whole milk room temperature

Instructions

Preheat the oven to 350F.

For the Topping:
Pour melted butter into a 9-inch round 2-inch-deep pie dish. Swirl to coat the bottom and up the sides of the dish. Sprinkle brown sugar evenly over the bottom of the dish.
Pat pineapple slices with a towel to remove excess liquid. Place one slice in the center of the dish. Arrange 6 more around it. If you’d like, cut 3 more slices in half and arrange them around the sides of the dish. Place a cherry in each slice’s center and fill in any other gaps between slices.

For the Cake:
In a medium bowl, whisk together flour, baking powder, and salt.
In a large liquid measure cup, whisk together sour cream and milk.
In a large mixing bowl or the bowl of a stand mixer with the paddle attachment, beat butter until creamy. Add the sugar and beat on medium speed until light and fluffy, about 3 minutes.
Add the eggs one at a time, beating until well combined before adding the next. Beat in the vanilla.
Beating on low speed, add a third of the flour, mixing just until combined. Add half of the sour cream mixture, beating just until combined. Continue alternating with the remaining flour and sour cream mixture.
Pour the batter into the pie dish and carefully spread to the edges of the pan.
Bake for 40 to 45 minutes, or until a toothpick inserted into the center comes out with a few moist crumbs. You may want to cover with foil after 30 minutes if the cake is already golden brown.
Cool the cake on a wire rack for 15 minutes. Place a cake plate or stand over the top of the cake and carefully invert. Cool for another 20 minutes or completely before serving.

GO FOLLOW MY FACEBOOK PAGE

Join this channel to get access to perks:
https://www.youtube.com/channel/UCW7cBq7rpDRaM1-y2CT6L0A/join

GO FOLLOW MY FACEBOOK PAGE
https://www.facebook.com/OLDSCHOOLSOULFOOD

GO FOLLOW MY INSTAGRAM PAGE
https://www.instagram.com/mr_old_school_soul_food

FOLLOW ME ON TWITTER

FOLLOW ME ON PINTEREST

FOLLOW ME ON TIKTOK

@oldschoolsoulfood

FOLLOW ME ON YOU TUBE
https://www.youtube.com/c/OLDSCHOOLSOULFOOD

Visit my website
https://www.oldschoolsoulfood.com

MY MAILING ADDRESS IS:
OLD SCHOOL SOUL FOOD
23501 CINCO RANCH BLVD
SUITE H120
PMB # 142
KATY,TEXAS 77494

EMAIL ME : CHEFJEFF@OLDSCHOOLSOULFOOD.COM

OLD SCHOOL SOUL FOOD
Phone number 281-345-8991

FOR CASH DONATIONS:
paypal.me/oldschoolsoulfood
cash.app/$wacjeff

MY OLD SCHOOL SOUL FOOD MERCHANDISE FOR PURCHASE LINKS:

https://www.amazon.com/s?rh=n%3A7141123011%2Cp_4%3AOLD+SCHOOL+SOUL+FOOD+FAMILY&ref=bl_sl_s_ap_web_7141123011

https://old-school-soul-food.creator-spring.com/

#oldschoolsoulfood
#justshowsomekindness
#oldschoolpineappleupsidedowncake

Hello my old school soul food family Chef Jeffrey back with another video all right y’all I told y i going to kind of change up the monotony of my channel a little bit here it’s still a uh right after the New Year y’all and I’m going to do something I

Never did before and bck box K wake up in the back back there you and Gina you and Gina back there acting up back there I’m going to take a box tape and I’m going to make now you see this cake on here I done did a lot of

Research y’all know I don’t do box cakes I’m not going to make that cake on that box I want to make a pineapple upside down cake with this I’m going kind of modify it a little I got a little recipe on the side so I’m going to take that

And uh kind of cook it in a cast IR Skillet here got a cast IR sket I’m now we going to hope I never did this before and it don’t stand on thing I did a cake in a cash SK it before and it come out

So I don’t know if this going to work or not it’s going to all be experimental what I’m doing here so I don’t know so hold on y’all just a second first thing I am going to do I’m going to spray this here really good let’s get it

Now like I say y’all I don’t know this going to work you going to pray that it works okay what I got here like I said I got the cake mix I got the cake mix requ as for I’m going to do it just like you say on the box

Three eggs a cup of water and a half a cup of oil for the cake mix and then the brown sugar butter go in the skillet here and I’m going add the pineapples and the Cherry just like a normal uh uh cake mix so let me uh uh uh German

Chocolate cake uh pineapple upside down cake so what I’m going to do let me get started here y’all and say put the butter in here first we’re going to pour that butter in there I pretty much know how to make a I almost say German T cake again I

Pretty much know how to make a find upside down cake you put this in the bottom of the pan well what I don’t want to do y’all I don’t want to break that up a little I don’t want to uh mess up my spray there yall know spray the bottom of the

Pan I know you you just sprad the brown sugar around like this I know that part move that butter around there so I have a nice pretty popping come out but like I said what I’m not trying to do y’all is trying to disturb the spray cuz I sprayed that

Really really good okay now we going to go in one I pineapples I know this part too the pineapples in there so we going to hope this works y’all hope we’re not eating it right out the skillet but if it do I’m going to show y’all I ain’t going to hide nothing from

Y’all y’all know me if it ain’t going to work I’m going to let you know it a work come out there get that right on there see we might go on the side with this bad boy too we’ll go on the sides with it as well

Y’all TR use all this pineapple out of here like I said this is one can which is 20 oz of pineapples 20 oz can of pineapple so we going to see what happens just breaking in a part y’all where it kind of fit in there put that bad boy right there and

That’s the whole can of pineapple now we going to go in of course yall know got to have the cherries so throw the cherries in there like I say y’all never did never did this before so y’all going to be laughing at me or applauding me or crying with me

However it come out we’re going to see y’all we going to see throw them cherries in there just like that there we go put one right there put one right there okay now we got that done now now we going to make the make the cake mix which is

Simple move y’all back over here got that done move y’all back over here if this works I be might not be making no more homemade cake mixes huh n yall know I love my homemade cake mixes okay and y’all this is the pineapple perfectly moist Dunkin hind I don’t know

How this taste never used this before but we going to see here y’all like I said make it easy on you for New Year y’all been baking all last couple of months for Christmas in New Year we going to make we going to do some easy stuff here

Y’all going to make it easy on ourselves okay let me get my mixer here here like you see on the box just pour all this stuff in here together and mix it together I got my eggs got some water here some oil I know it’s going to be

Moist it’s got oil in it right I know that already okay to brend this [Applause] together Move that around now place that [Applause] [Applause] [Applause] around all right [Applause] all right y’all that should do it right I hope okay let’s get rid of this throw that right there now kind of mix that up there all mix together and get our get our Skillet here and we just going to pour this right on top of the pineapple y’all like

I said y’all we just going to see what happen here either I got a mess I done created something good here what y’all think what y’all think leave comments what you think here since leaving the comments you going to know you going to cheat okay y’all it say 350° oven for

About 30 35 minutes so we going to come back y’all and we going to see what concoction Chef done come out with old school pineapple upside down cake made with a box cake y’all anyway we’ll be right back all right y’all we are back this actually took 40 minutes to cook

Y’all 40 minutes it’s definitely done so y’all know it’s a thin line between taking it out too early and not taking it out on time so I’m going to let it sit about 3 minutes y’all in the skillet here I got my pan my plate here to flip

It on and we’re going to prepare for the worst and hope for the best right so anyway we’ll be back once I flip this out and we’re going to see what happens we’ll be right back all right y’all we are back here all right y’all here we go what they say here goes

Nothing here goes nothing huh oh that’s still hot up Jeffrey still hot shoot accident prone H okay here goes y’all what we going to do I’m going hold this with this hand flip it with my other hand here so here we go y’all pray for the best PR for the

Worst oh my goodness okay some of it want to stick hey it ain’t no big deal I’m just going to put it right back in there like that ain’t we ain’t we ain’t no big deal y’all put it there just like that look at that there put that right

On there even though it don’t go there and one on the side right there hey my bad huh not bad look at that y’all look at this all in the cast IR Skillet and with uh and with the store bought box cake boxcake Kenna you hope you proud box Kenna probably smiling right

Now look at that y’all look at that old school upside down pound cake with the inside help so anyway I’m going to step off cut a piece we’re going to Pat back and see how it really tastes is it nice and moist so we’ll be right back all right y’all we

Are back here look at that nice cake there look at this here look at that pineapple upside down cake hey made by box cake dck box cake Kenner style box like I said y I ain’t never made no box cake upside down cake and I never did

One in this black Skillet what I call Black and skillet cast down Skillet sometime you don’t know if they seasoned well I know my SE I know my Skillets are seasoned well where they don’t stick but with a cake it’s like a different procedure so enough talking y’all let’s

Go in here go in here and see how moist this thing is now look at that there look at this here going in here not bad y’all actually it’s pretty good it ain’t not bad and I’m not a fan of cherries y’all I’m going to take them off I love

Pineapples I got the little caramelized pineapple right there all that brown sugar butter that’s try little in piece there crust look at that that’s a good part there we got that like a brown sugar soaked in there with that with that butter pineapple juice going in God yeah the part right here

That’s the point right there y’all how all the good stuff here right at the corner so anyway like I say y’all ain’t no really recipe for this I’m going to put down what I put in it right off the box but there one more piece here not bad and the

Pinch do I approve absolutely absolutely y’all so hey like I say this year I’m going to be taking it easy I’m going to be doing a lot of homemade video don’t worry I’m going to do a lot of shortcuts and like I said I found uh figure out a lot of

People ain’t got time and they got busy with life to do a lot of stuff from scratch and I know a lot of shortcuts you can do a lot of healthy items I can show y’all and that’s what I’m going to do this year hash come out next year next year next

Week y’all we still doing the 2023 hashtag even though it’s 2024 so anyway if you like the video please share please comment Please Subscribe please follow my other social media account Facebook YouTube Instagram Twitter Twitch TV Pinterest old school.com remember the hash 2023 just show some kindness old school soap until

Next time have a blessed old school soap day and I will definitely see y’all in the next video y’all have a happy blessed weekend love y’all bye

35 Comments

  1. Chef Jeff that's how my grandmother always made her pineapple upside down cake. I have followed her and make mine the same way!! It has always turned out and so good now you got me craven that cake😊 GOD BLESS YOU CHEF JEFF 🙏 🙏🙏🙏

  2. I think you've created something good. Hello chef jeffery. Good old layer back cold and rainy day here in the Carolinas. Be right over.

  3. I’ve never made pineapple USD cake in anything other than cast iron. Always turns out perfect!

    I started with a recipe for it and ended up halving the cake recipe and doubling the topping recipe. That’s how I like it. Less cake and more of the gooey, delicious topping!

  4. Not bad at all!! 🍍🍒❤ I'm definitely going to make this. So Good!!! Thanks for sharing. Wake up, Kenneth and check this out!! 🙌
    🙏

  5. Chef, it worked beautifully. I accidently bought tidbit pineapple 😮. But I just flipped it and it looks fabulous. Thanks 😊😊.

  6. This pineapple upside down cake looks beautiful and delicious I hope you and your family and your friends had a wonderful Christmas and New Years God-bless you all! ❤🎉

  7. What a throw back, Chef. My dad made this cake on each of my childhood birthdays.
    I haven’t experienced it in the cast iron skillet, but I think I will attempt it but a homemade version.
    Thanks for bringing back wonderful memories!!!😊🎉❤

  8. Chef Jeffrey, I have not made an upside down pineapple cake in a long time. This cake looks so delicious and cake wait to make it in the pan. Thanks for the quick recipe. Stay safe.

  9. Mom always used a cast iron skillet but usually from scratch. BCK is asleep in the back pew. Gina, well she's sipping in the bathroom 🤣

  10. Chef Jeffrey I love the steps and process of how this cake was prepared. You make food look so delicious. Thank you for sharing! Be Blessed and stay safe everyone!

  11. I would have did the same thing but by me beening extra, i would have added pinapple flavoring to enhances the flavor.

  12. Hey Chef Jeffery!! I have made pineapple upside down cake in a iron skillet and it came out good. So I knew yours would too. 😋Cheers!! ❤😊

  13. Good morning Chef and everyone, happy Sunday!
    Well, no tears shredded Chef, you know how to work the magic!!🎉🎉
    Thank you for the option, I would have never thought to do that in the cast iron skillet.
    Take care everyone and enjoy the day!❤❤😊

  14. Oh wow my mom use to make this cake from scratch never put 🍒 on it the way she use to flip that cake out of that cast iron skillet was amazing 😊

  15. Looks great, but I was looking more to see how your finger healed up, lol… I see no bandage, so must be all grown back just like you said.

  16. Looks great–love pineapple! Going to make this plant-based as I have a family history of Cancer so need to avoid the estrogen and possible BLV in dairy and choline and lead in eggs. Thanks so much for sharing

  17. Happy New Year Chef Jeffery, as usual you knocked this out the park. Looking forward to whatever you choose to share this year!!

  18. Hey Chef Jeffery! That Pineapple Upside Down Cake looks really good.😋 It came out nice in that skillet. Thanks for sharing. Blessings 🙏💘

Write A Comment