WITH GLISTENING RINGS of
sweet-tart pineapple and ruby pops of
maraschino cherries adorning a but-
tery, tender yellow cake, the pineapple
upside-down cake is one of America’s
most iconic desserts. At its most basic,
the dessert is a stir-together yellow
cake baked atop butter, brown sugar,
canned pineapple rings, and jarred
cherries and then inverted once baked
so the fruit is on top.
My colleagues and I sampled five
recipes for this cake, and we were
surprised to find that while the cakes
looked great, they simply weren’t as
delicious or as special as they should
have been. To start, the cakes them-
selves didn’t have pineapple flavor,
and the toppings had metallic notes
from the canned fruit. The versions
we tried with chunks of fresh pineap-
ple were better, but we all missed the
retro beauty of the rings. Plus, all the
cakes we tried looked a little dull and
lacked a glossy caramel sheen.
We decided it was time for an
update. I wanted my version to have
loads of fresh pineapple flavor; a
moist, buttery, simple-to-make yellow
cake with pineapple flavor of its own;
and a stunning, glossy look that am-
plified the iconic appeal of the rings.
I began by cutting a fresh pineapple
into ½-inch-thick slices. Then I used
round cutters to punch out clean
circles and remove the tough core. I
set the rings in a greased 9-inch round
cake pan with generous amounts of
melted butter and brown sugar (which
would cook into a caramel). I thenPineapple
Upside-Down
Cake
This beautiful retro
cake deserved an
update—and kicking
the can(ned pineapple)
was just the start.
by Matthew Fairman