This cocktail dates back to the 1870s, and was most likely invented in by a bartender in Chicago. It was known as the Continental Sour and the Southern Whiskey Sour before New York Sour stuck.
Here's how to make one: Mix 2 ounces of rye or bourbon whiskey, with 1 ounce of fresh lemon juice and 1 ounce simple syrup in a cocktail shaker. Fill with ice, close, and shake for 30 seconds. Strain into an ice-filled glass. Hold the back of a spoon over the top of the drink and pour 1/2 ounce fruity red wine. This will make the wine float on top, creating the distinctive look and flavor.