In the bottom of an old-fashioned glass, carefully muddle the sugar, Angostura, one orange slice, one cherry, and a splash of water or soda. Remove the orange rind and add the bourbon, ice, and water or soda. Garnish with the remaining orange slice and cherry.
The Old Fashioned was created at the Pendennis Club in Louisville, Kentucky. There are two warring camps of Old Fashioned drinkers: those who muddle the fruit and those who don't. I belong to the first camp, as the muddling adds so much flavor. Those other guys just want some sweetened whiskey, not an Old Fashioned. The 1862 Whiskey Cobbler — the granddaddy of this drink — was shaken with two pieces of orange in the bar glass, so we have history on the muddling side. Shaking the fruit with ice will have the same effect as muddling. Or you can do both.