Like a Manhattan, the Old Fashioned is a quintessential bourbon cocktail. Legend holds that it was invented in Kentucky, which may place it at the top of the list of all bourbon cocktails.
The history of the drink that I choose to believe is that an Old Fashioned was created around the turn of the 20th century by Colonel James Pepper, a Kentucky bourbon distiller, and a bartender at the Pendennis Club in Louisville, KY. It has also been said that the Old Fashioned may have been the first mixed drink to be called a "cocktail." However, I think people said the same about a martini, so who knows for sure. Anyway, I think it's fair to say that the old-fashioned glass was, in fact, named after the drink.
An Old Fashioned is made by placing a sugar cube/teaspoon of sugar in an old-fashioned glass and soaking it with a few dashes of Angustora bitters. After the sugar and bitters have mixed, add enough club soda to cover the sugar and then muddle it all together. Next add the bourbon (however much you want, we're all adults here....) and a splash more of the club soda. You can garnish it with an orange slice and maraschino cherry should you want to. I usually do if I have fruit handy as it definitely completes the drink. If you are extra ambitious, you can also add a twist of lemon to finish it off.
The Old Fashioned is a sweet, refreshing cocktail. It was once called a "palate-paralyzer," but I'm glad that name, or more specifically misnomer, went to the wayside - "palate-pleaser" is much more accurate.
I enjoy Old Fashioneds very much, and I guess Cole Porter did as well, as he wrote "Make it Another Old-Fashioned, Please." A smart guy, that Cole Porter.