How to make the perfect pineapple upside-down cake – recipe

Felicity CloakeWed 14 Apr 2021 12.00 BST

This slab of sponge with its cheery ring of pineapple is one of my few positive memories of school dinners (all of which, I now realise, centre on foods consumed with custard). Unlike the Gypsy tart, however, which seems to have been created for the express purpose of filling up Kent’s schoolchildren with minimum expense, the upside-down cake has its roots in medieval griddle cakes, and sophisticated French relatives in the form of the gateau renversé, which evolved into the tarte tatin.

Pineapples, however, were far too rare and costly to waste in such fripperies – far better just to hire one to show off to your friends – until James Dole’s Hawaiian Pineapple Company decided to put them in tins and market them to the public through the medium of upside-down cake. This old idea became the hottest bake of 1926 and, where America leads, Britain eventually follows; as Nigel Slater recalls, pineapple upside-down cake was “as exciting as cake got in 1960s Wolverhampton”, while Jamie Oliver waxes lyrical about the version served at his Essex primary school two decades later.

Frankly, I still get quite excited about cake of any sort, but this is a particular pleasure to make, because of the theatre involved – and the way even the most slap-dash of bakers can turn out something surprisingly impressive-looking. Lumpy custard, up to you.

The fruit

Though the fresh sort is available year round at my local garage, most recipes remain loyal to tinned pineapple in either juice or syrup: Nigella Lawson, who admits in Nigella Express that she has only “vague nursery memories” of pineapple upside-down cake, goes as far as to say she feels it “slightly bad sport to start peeling and slicing your own pineapple”. Only the recipe in Jamie Oliver’s Comfort Food calls for fresh fruit.Advertisementhttps://a20ca6bd6cc1f844f4f09633f13a318f.safeframe.googlesyndication.com/safeframe/1-0-38/html/container.html

Which you choose depends on what you’re looking for. The perfectly even slices of tinned pineapple look more impressive, cut out a lot of faff and will give you something closer to the cake you may remember from school, but the acidity of the fresh fruit makes it a more complex dish, so I’ll leave it up to you. Whichever you use, make sure you pat the fruit dry, as Rahul Mandal recommends, because this will help it caramelise rather than steam underneath the batter.

If you go for tinned pineapple, I’d choose the stuff in juice; not only is fruit in syrup now practically an endangered species, but you can use the juice to add flavour to the sponge itself. Lawson reckons this also helps make it “light and fluffy”, though it’s wise to add a little bicarbonate of soda, as she does, to balance the acidity and pour it in only at the last minute to minimise the disruption to the rise. (Note: if you’re using fresh fruit, you’ll need either to juice some of it or to buy a carton of juice.)

Glace or maraschino cherries are a more recent addition; earlier recipes seem to have preferred nuts such as the pecans in Michael Kors’ version (yes, that Michael Kors; it was published in Vogue, which is not my normal point of reference for this column, but I like to think I leave no stone unturned in my quest for perfection). It’s hard to match the flash of colour that cherries offer, but feel free to leave out the cherries, and/or use nuts, prunes, apricots or other dried fruits instead, if you prefer. Pecans may not look as pretty, but they do add a satisfying crunch.

The base

Lawson lightly butters and sugars the base of her tin, while Mandal and BBC Good Food’s Sara Buenfeld both make a butter and sugar paste, spiced with ginger in Mandal’s case, to sit underneath the fruit. Oliver deploys a method familiar to me from tarte tatin, melting butter and sugar until molten, then adding the fruit and leaving it to turn “a dark golden” in the pan before arranging it in the cake tin and drizzling the caramel over the top. Delicious, but it leaves the pineapple chewier than I’d like.Advertisement

The flavour, however, is great, so I’ve settled on Kors’ compromise, which melts the butter and sugar in the tin before adding the fruit off the heat, then leaving it to brown slightly without releasing too much juice in the process. Kors, who credits his recipe to his Grandmother Bea, “a high-school principal who loved fashion, style and baking”, recommends using a “cast-iron skillet”, which “helps it caramelise while baking”. I don’t have a suitably sized cast-iron pan, and it’s a risky idea to make this cake in a loose-based tin, whatever Oliver says, so I heat a flat cast-iron griddle in the oven instead and put the cake on top, which, though by no means key to success, helps to colour the base.

Kors, Buenfeld and Mandal all use brown sugar for this stage – dark brown, in Mandal’s case – which is a great way to add to the toffee flavour without caramelising the sugar to the extent that it will set rock hard. A little crunch around the edge is a happy textural treat, but the fruit should remain juicy.

The sponge

Not much in the way of variation here. Oliver, Buenfeld and Lawson use the classic pound-cake formula of equal parts flour, butter, caster sugar and eggs; Kors adds two extra egg yolks in place of some of the butter, which gives his cake a certain soft heft; and Mandal uses half dark-brown sugar and half caster. I don’t want to cede any of the butter, because the flavour works so well with the fruit, but I am going to include some light-brown sugar to echo the caramel flavour on top. Buenfeld and Mandal both add baking powder to their self-raising flour, which is a good way to ensure really fluffy results (I prefer plain flour, so I’ve added an extra teaspoon to that instead).

Curiously, many of the recipes, perhaps because they’re written for busy family cooks, suggest an all-in-one method, but, unless your butter is really squidgy, I think it’s always safer to cream it with the sugar first for a smooth result. Mandal is the only one to make his sponge in the classic school traybake style, as opposed to a round tin. Clearly this makes it larger, but as I see this as something to be eaten in chunks slathered in custard, rather than in delicate slices with a fork, it feels more apt. Fortunately, it keeps well, so you don’t need to eat it all at once.

The flavouring

Kors and Buenfeld both add vanilla extract to their batter which, for once, I think actually earns its place: that perfumed sweetness is more than balanced by the robust acidity of the fruit. If further tropical flavours appeal, Oliver’s coconut paste, made by heating desiccated coconut with coconut milk, may be something to consider: like piña colada in cake form, according to one of my testers (which makes me wonder if I should have soaked it in rum, too).

Mandal goes down a different, spicier route with cardamom, chilli and ginger powders, and chopped stem ginger, which gives his sponge a distinct and pleasant warmth that puts us in mind of a rather fancy Jamaica ginger cake. Clever but, like Oliver’s, not the pineapple upside-down cake you’re likely to be nostalgic for. If you’re after something a bit different, however, it comes highly recommended.

The topping

Though not strictly necessary (rather like the cake itself), a final drizzle of flavoured syrup will give you attractively glossy results. Oliver makes a tangy lime juice and ginger version, while Mandal sticks to a simple brush of golden syrup, which does the trick more quietly. If you happen to have some stem ginger in syrup, or indeed some of the syrup from the maraschino cherries you may have used on top, that would be even better.

Though sturdy enough to take on a picnic, I think this is best served warm, preferably with a lot of very thick custard. Each to their own, though.

Perfect pineapple upside-down cake

Prep 35 min
Cook 35 min
Makes 12 squares

For the topping
1 large ripe pineapple, or 12 tinned pineapple rings in juice
75g butter
100g soft, light-brown sugar
30 maraschino or glace cherries (optional)

For the cake
250g softened butter, at room temperature
125g caster sugar
125g soft, light-brown sugar
4 eggs
240g plain flour
3 tsp baking powder
½ tsp bicarbonate of soda
½ tsp fine salt
1 tsp vanilla extract
3 tbsp pineapple juice (from the tin, if using)
2 tbsp golden syrup, sugar syrup, runny honey, or the syrup from maraschino cherries or stem ginger, to finish (optional)

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Start by preparing the pineapple, if necessary: slice off the peel, remove any “eyes”, then cut in half, remove the core and slice into roughly 1cm half-moons. Put the slices between two pieces of kitchen paper to dry (and do the same if using tinned rings).

Put a roughly 30cm x 21cm baking tin on a low heat and melt the butter and sugar for the topping until bubbling. Take off the heat, arrange the pineapple rings in a pleasing pattern on top, then put a cherry, if using, in the centre of each.

Heat the oven to 180C (160C fan)/350F/gas 4 and, if you have one, put in a bakestone or cast-iron griddle in there to warm up. In a large bowl, cream the butter and sugar until light and fluffy, then beat in the eggs one by one, making sure each one is well incorporated before adding the next.

In a second bowl, whisk the flour, baking powder, bicarb and salt, then fold this into the batter mixture, followed by the vanilla extract. Add enough pineapple juice so that the batter drops easily from a spoon, but does not run off it.

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Spoon the batter on top of the pineapple in the tin, smooth out the top and bake for 40-45 minutes, or until well risen and just firm in the centre.

Remove, leave to cool in the tin for five minutes, then run a spatula round the edge to loosen and carefully turn out on to a board. Brush with syrup, cut into portions and serve warm with custard, ice-cream or cream.

 Pineapple upside-down cake: does it bring back happy memories of school, or is there another favourite pudding you’d prefer to see pop up in the column? And what other fruits lend themselves well to the same topsy-turvy treatment?