Pineapple Upside Down Cake With A Side of Cookies

The other day, I got a very nice compliment on my recipe for Gingerbread Peach Upside Down Cake (really my mom's), and it dawned on me that I've never even had the original upside-down cake: pineapple!  I suppose it's no accident.  Pineapple upside-down cake traditionally involves the horrific combination of canned pineapple and maraschino cherries.  I find the combination no more appealing congealing atop a slice of syrup-shellacked cake.

When I saw a recipe for pineapple upside-down cake in Thomas Keller's Ad Hoc cookbook, I had to reassess.  Surely Thomas Keller wouldn't put his stamp of approval on an unworthy dessert!  Mr. Keller's admitted taste for canned pineapple aroused my suspicions, but the recipe called for fresh and I've never met a Keller recipe I didn't like, so I forged on.

The sugar topping of the recipe also intrigued me... instead of sticking to the usual brown-sugar and butter combo, Keller invented a "schmear": a fluffy concoction of whipped butter, brown sugar, rum, vanilla and salt. 

Oddly, the recipe only calls for a fraction of the schmear, and Keller unhelpfully advises that you can save the remaining schmear in your refrigerator for up to two weeks (or frozen for 1 month!).  What am I supposed to do with a big bowl of schmear in my refrigerator? Make five more pineapple upside-down cakes in the next two weeks?  At this point in the recipe I wasn't even entirely sure I liked pineapple upside-down cake so the remaining schmear's fate seem precarious at best.

Of course, the schmear proved to be evilly delicious.  As I stood over the sink, licking the sugary, rum-spiked butter from my fingers, the spoon, and the bowl, I simply couldn't bear to wash it down (the sink, not my throat--let's just say its a good thing I didn't have a glass of milk handy...). Since I'm the only one crazy enough to eat it by the spoonful, I had to find some way to use it in order to save myself from a diabetic coma.  Enter Keller-Schmear Cookies!  The schmear closely resembled cookie dough pre-eggs and flour so I just tossed in a few more ingredients, and viola!  Side of cookies!

Now, I know what you are thinking: I made a batch of cookies so that I wouldn't be dessert-less and disappointed when my first bite of cake confirmed that pineapples taste better on pizza and peaches taste better on upside-down cake.  Not so!  I trust Thomas Keller... even though he likes canned pineapple.

The pineapple upside-down cake proved to be quite good, although I personally prefer gingerbread-peach.  And the Keller Schmear cookies?  Maybe it was a little weird to serve cookies with cake, but I think my cookies were better!  I should change this post Keller-Schmear Cookies with a Side of Cake.  And Thomas Keller should include them in his next cookbook! 

Ingredients

Keller Cookies + Schmear
1 stick unsalted butter, room temp
1 1/2 T. honey
1/2 t. dark rum
1 c. packed light brown sugar
1/4 t. vanilla extract
1 egg
1 c. flour
1 scant 1/2 t. baking powder
1/2 t. kosher salt

Upside Down Cake
1 pineapple
1 stick unsalted butter, room temp
1 1/3 c. flour
2t. baking soda
1/2 c. plus 2 T sugar
1/2 t. vanilla extract
2 eggs
1 T + 1t milk

Preheat the oven to 350.  To make the schmear and cookies, combine the brown sugar, butter, honey, rum, and vanilla in a medium bowl and beat with a hand mixer until smooth.  Spread 1/3 cup of the schmear onto the bottom of a 9 in. cake pan, sprinkle with kosher salt, and set aside.

Mix 1 egg into the remaining schmear until well-blended.  Add the flour, salt, and baking powder and mix until combined.  Refrigerate the cookie dough while preparing the pineapple.

Hack off ends of the pineapple, cut away the fibrous peel, and slice into rounds or half-rounds.  Remove core from the rounds (or half-rounds) and arrange in the pan on top of the schmear (you won't need all the pineapple... for a scrumptious way to use up the leftover pineapple--besides just eating it--try my recipe for Pineapple A La Cabo).  Go back to making cookies.

Form the chilled cookie-dough into balls (think ping-pong), roll in granulated sugar, and place on a cookie sheet 2 in. apart.  Bake at 350 for 10 min.  Cool while you make the cake.

Sift the flour and baking soda together and set aside.  In a large bowl, combine the butter and sugar.  Beat on medium speed for three minutes until light and fluffy.  Add the vanilla, and beat to combine.  Add the eggs, one at a time, beating well and scraping down the sides after each addition.  Beat in the milk.  Add the flour in 3 batches, stirring with a spatula until just combined (do not overmix! overmixing = tough cake).

Spread the batter over the pineapple, pop in the oven, and bake 15 min.  Turn the pan 1/2 turn to ensure even baking, and bake another 20 minutes or until a knife inserted into the cake comes out clean. Cool cake for 30 min before inverting onto a plate.

Serve with freshly whipped cream (beat 1/2 c. heavy whipping cream 'till soft peaks form, add 2T granulated sugar and 1/4 t. vanilla, beat gently to combine), and to really dress it up, a glass of Sauternes (a shout-out to the person who inspired me to write my first post in over 4 months!).