Though the Sherry Cobbler is far and away the most famous of the genre, the Madeira version is the first known mention of the drink on record. Even more popular than sherry in the eighteenth century, it’s no wonder Madeira made a splash in the new style of iced drinks that emerged in the decades before the Civil War. Stone fruit and ginger compliment the wine and so do the fortifying spirits of brandy and aged rum.

The Sherry Cobbler came on the scene in 1838 and in a matter of years it was known across the United States and was poised to take over the world. A simple mixture of sherry, sugar, and citrus shaken with ice, served over ice with a straw, and garnished with abandon. For this recipe, I stuck to the classic orange and lemon, pineapple syrup (inspired by an 1880s Harry Johnson spec) and a blend of oloroso and PX sherries.

It’s only natural that for a template that centers fortified wine would extend to the third member of the great Iberian triumvirate: port. The first published recipe I can find for a Port Cobbler is in Harry Johnson’s 1882 book. I love ruby or white ports in cobblers and for this recipe I combined tannic ruby port with blueberries and a 1:1 vanilla syrup. I really like currant and cherries spilling out of this drink in a goblet.

Though vermouth became part of the American drinks landscape after the Sherry Cobbler’s heyday, it nevertheless makes a fantastic base for Cobblers. The Torino Cobbler illustrates this point while also reflecting how the Cobbler template has found a home in twenty-first century bar culture, where it sees favorite modern products work their way into recipes.

Named for the main character in The Secret Garden, this iced beauty combines the aesthetics of the Fix and the Bramble in a charming presentation. The malty genever base provides a canvas for the classic English flavors of rhubarb, ginger, and blackberry.

Like many of the Black culinarians we’re learning about this month, Thomas Downing was not considered a bartender, but a restaurateur who ran an oyster cellar and catering business. But we know he served drinks at his establishment and, as Cobblers were the order of the day, I opted to create one with Madeira and brandy which were en vogue in New York City during Downing’s heyday.

I love the classic idea of having nuts, chocolate, and dried fruit with coffee and port after dinner. For this recipe, I leaned on the idea of Sangarees and Cobblers, layering flavors over a tannic base and drying the whole thing out with a half-ounce of rye. Pebble ice and a very Victorian garnish make this one quite festive indeed.

I love making all manner of Cobblers during the summer when every month brings a new bounty of fresh fruit. But I’ve always wanted to adapt a Cobbler for peak fall and Madeira is the perfect wine for it. I love looking at old pear and apple varietal names and took the name for this drink from a type of pear that’s still grown in western Massachusetts.

I wanted to demonstrate a fancy application for our Club Pimm’s, and I immediately thought of doing a Pimm’s Cup Royale, i.e. topped with Champagne. I also wanted to integrate some of the traditional fruit and mint that are used in Pimm’s Cups and decided a Cobbler format would be the perfect vehicle. Served over crushed or pebble ice, our Pimm’s Royale is, naturally, garnished with abandon.

My devotion to fortified wine and obsession with 19th-century cocktail aesthetics makes the Cobbler one of my favorite genres. This one combines my love of aperitivo and olde American drinks. Classic Torino-style vermouth, Campari, grapefruit, Sfumato, and strawberry made for a great combination, especially ideal for spring.

In this interpretation of a cobbler, smoky Mezcal and piney gin team up with off-dry blanc vermouth, lime, cucumber, and parsley for a verdant spring cocktail.