Are there drinks/cocktails involving vinegar? Being a huge fan of vinegar, I recently wondered if there are any actual known cocktail recipes/drinks that involve vinegar as an ingredient, preferably as a significant ingredient contributing perceivably to the drink's taste.

While there are drinks with a more spicy/hearty flavour, like Bloody Mary, I never heard of a cocktail involving vinegar and wonder if it would even work together with alcohol from a flavour-perspective. I could imagine the best targets to be spirits with a rather low-profile taste of their own, like vodka.
There is a whole class of drinks called Shrubs

Shrubs usually involve a base syrup made from vinegar and fruits and spices and then mixed with a spirit. 

Shrub syrups are available online in a variety of flavors and there are plenty of recipes out there too for creating your own Shrubs at home. 

My experience with and what I would define as a example Shrub would involve a shrub syrup, fresh fruit muddled in it with a spirit and then mixed, topped off with crushed ice and soda water.