An old fashioned was one of the simpler and earlier versions of cocktails, before the development of advanced bartending techniques and recipes in the later part of the 19th century. It's rich, smooth and silky taste is equal to its 'reputation' as a drink for the macho-man who is too rich, smooth and silky.
The Pendennis Club, a gentlemen's club founded in 1881 in Louisville, Kentucky, claims the old fashioned cocktail was invented there. The recipe was said to have been invented by a bartender at that club in honor of Colonel James E. Pepper, a prominent bourbon distiller, who brought it to the Waldorf-Astoria Hotel bar in New York City. Cocktail critic David Wonderich finds this origin story unlikely however, as the first mention in print of "old fashioned cocktails" was in the Chicago Daily Tribune in February 1880, before the Pendennis Club was opened; this in addition to the fact that the old fashioned was simply a re-packaging of a drink that had long existed.