This pie was a challenge. I knew it would be. Pineapple Upside Down cake, in a pie? Do I turn it into a pineapple fruit pie? With maraschino cherries? Or do I stay true to the classic cake and somehow turn it onto a crust, so it's truly upside down? I opted for the latter. And boy I am glad I did! 
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There were a few issues with my crust edges baking off, so I've altered the recipe to make those corrections!

You'll need 1 truly flaky crust, butter, brown sugar, canned pineapple slices, maraschino cherries, milk, sugar, shortening, vanilla extract, and baking powder. Am I missing any ingredients? Maybe. So best to see recipe below. ;)

Melt butter directly in your pie pan.

Sprinkle brown sugar over melted butter.

Lay pineapple slices atop brown sugar and butter. 

Fill the openings with maraschino cherries. I used whole cherries, and it made my cake a tad pink, I'd recommend cutting them in half or slicing them into thinner pieces before placing them in your pie tin so your caramel color is a little more brown.

Mix your cake batter...

...until smooth like this!

Gently spread cake batter over fruit...

...and keep going...

...and going... until all your batter is in the pie pan.  Smooth batter over any pieces of fruit poking out.

Lay your truly flaky crust over the batter...

...crimp up (remember you're going to flip this baby over, so the imperfections in the crimping need to be facing up so that when you turn it over the crimp facing up looks purdy! Here's my suggestion: Don't crimp to the edges to the edge of the pie pan. Crimp to the edge of the cake batter, but don't let your crimping hang off the edge of the pie pan like you would on a normal pie, or it MAYYYY (most definitely will) melt off mid bake, forcing you to piece together your crust edge for your final product...

See what I mean? It's okay, we'll salvage those bits of crust later. Let pie sit for 10mins before turning over. But don't let it cool completely or your slices of pineapple might stick to the pan!

Garnish with fresh maraschino cherry. With the stem!

It turned out better than I had hoped! Delicious vanilla cake, topped with caramelized pineapples and cherries all over a TRULY flaky crust! Mmmmm...

Oops. So in the Musical this pie is called Mermaid Marshmallow, but the in the movie it's Marshmallow Mermaid. Oh well, still a delicious marshmallow pie either way right? I've been waiting to bake this one. Because I knew it had to taste and look so good. This is THE pie that people remember from the movie, and is probably the most recreated recipe from Waitress. There is a popular recipe for this pie online. It involves a graham cracker crust, coconut mixed into the crust, and chocolate bits in the whipped cream. I'm sure that version is delicious, but I wanted to create a pie that looked a little cleaner, and used marshmallow pudding as the main ingredient. This pie is sweet, cute, and delicious! 

Here it is! The BIBLICALLY good pie that made Dr. Pomatter fall for Jenna at first taste: "Marshmallow Mermaid Pie: Truly flaky crust, filled with a pillow of gorgeous marshmallow puddin', and a layer of freshly whipped coconut cream. Topped with pink and green mini marshmallows and sweetened shredded coconut."

Gather your gelatin, water, egg whites, FunMallows. (I didn't end up using the marshmallow creme.)

Prepare your truly flaky crust, crimp the edges.

Blind bake your crust.

Whip up your marshmallow puddin'!

Spread marshmallow puddin' in your baked crust.

Layer coconut whipped cream atop the puddin'.

Be generous! Pie must be HIGH!

Decorate edges with FunMallows in circles along the crust.

Decorate with shredded coconut in the middle!

Serve, slice, and enjoy! And don't give this to your gynecologist. As he might fall in love with you upon first bite. After all, it only takes a taste.

This is a great pie idea in theory right? What can go wrong? Blueberries? Yum. Bacon? Extra yum. Hmmm.. turns out there is quite a lot that can go wrong. Not going to lie to the blogosphere, this was attempt #2 at Deep (Shit) Dish Blueberry Bacon Pie. First attempt, was truly a DEEP and SHITTY disaster! I'll describe attempt #1 for your amusement: "Blueberries baked in a truly flaky crust with bits of crisped bacon, topped with a bacon lattice".

Well. I should have known using a whole pack of bacon would be complete overkill. But I had to use that much for the taste of bacon to come through right? Wrong. DEEPly wrong. As the raw bacon lattice cooked atop the pie, all the grease from the bacon dripped right into the blueberry filling, causing there to be far too much bacon grease in a pie. There was so much bacon grease in the pie, as we took the pie out of the fridge the next day, we had to wonder... what are these white solid bits of things my pie??? Solidified bacon grease. That's what. While the lattice idea was cute, and looked very even before being placed in the oven, the bacon strips shrunk while baked. Leaving me with bacon lattice that didn't even touch the crust edge.

Okay. Lesson learned. Too much bacon overpowers the blueberries, raw bacon cooked in the pie leaves a cup and a half of bacon grease in the pie, and cooked blueberries might not be the best pairing with bacon. So back to the drawing board. After the suggestion of my official pie taste tester Jonathan, to use fresh blueberries instead of cooked, I decided to turn this Deep SHIT Blueberry Bacon into Deep DISH Blueberry Bacon. A cream pie so delicious it is worthy of being on Jenna's Pie o' the Day Board. One worthy of: "It sold so fast today I couldn't quite believe it!" -Jenna

So here is Attempt #2. And it is perfect. Truly. "Deep (Shit) Dish Blueberry Bacon Pie: Freshly whipped maple cream, with fresh blueberries in a truly flaky crust. Topped with maple icing, and sprinkled with bits of crispy fried bacon."

Crisp your bacon an a skillet.

Add maple syrup to freshly whipped cream to create a maple cream.

Fill truly flaky crust with maple cream.

Make maple icing with powdered sugar and maple syrup.

Pour icing into a plastic zip-loc bag.

Pour fresh blueberries over maple whipped cream.

Cut hole in bag with icing, and drizzle over blueberries.

Sprinkle bacon bits over the blueberries and icing.

Slice, serve, and enjoy! Let the combination of sweet maple cream, fresh tart blueberries, and salty crisp bacon take your taste buds out of this world! And be careful, because this one will go quick!