The Sherry Cobbler is reported to have been the most popular drink in America around 1888 (according to David Wondrich's Imbibe!). It was also a hit elsewhere in the world and spawned a number of similar wine cobblers made with a variety of wines of the time that are for the most part extinct today. The cobbler style of cocktails can be made with any base -- commonly brandy or whiskey are used in place of the sherry. The keys to any cobbler are crushed ice, sugar, and a heaping of fresh fruit for the garnish.
There are two types of sherry: Fino and Oloroso. Fino is drier and with that, would do well with the amount of simple syrup suggested below. For the slightly richer Oloroso, it is recommended to use half that amount.
Note: The original cobbler recipes use 1 tablespoon of raw sugar, typically dissolved in water prior to mixing to avoid granules in the drink. In order to avoid this, just use simple syrup in the recipe.