It seems that the addition of muddled fruit originates during prohibition when the quality of the whiskey went down drastically and the average speakeasy patron needed something to help mask the god-awful taste of backwoods bourbon. The historical significance alone should give this variation its own place in every bartenders repertoire.
My formula for this is similar to the one I use without fruit. I decrease the amount of simple syrup by half to compensate for the addition of the fruit, and decrease the amount of bourbon slightly since I tend to serve these mid-day and nobody likes to find their guests face down on the croquet pitch with only mad dogs and Englishmen standing about. The steps to build it are much different though. Start with an orange slice, about ¼ inch thick. Peel the fruit from the inside of the slice and place it in the bottom of an old fashioned glass. Take the peel and slice it into two pieces, place these on top of the fruit; add two cherries, two dashes of angostura bitters and muddle. Pour in ½ ounce of simple syrup, an ounce of the bourbon of your choice (I suggest Gentleman Jack), stir well. Fill the glass with ice and add the remaining 1 ½ ounces of bourbon.
The garnish on this drink comes from my oldest and best cocktail companion who will remain nameless to protect his professional reputation. I fell it adds the perfect finishing touch to this drink. In order to comply with rule number two (look to the left of the screen) we need to include a cherry. It pains me greatly to write this as this is the only circumstance where I use them, but the neon red maraschino cherries work best here. You will also need a half an orange slice and a toothpick (I’ve been partial to the little plastic swords since I was a kid). Fold the orange in half around the cherry and stick the sword through to hold it all together, place it flippantly across the top of the drink and the side of the glass. Serve this cocktail with a nod to Utah for being the 36th state to ratify the 21st amendment, repealing the 18th amendment, and ending prohibition!
2½ oz bourbon
2 dashes angostura bitters
½ oz simple syrup
1 ½, quarter inch thick orange slices
Place the fruit from one orange slice into the bottom of an old fashioned glass, slice the peel into two pieces and add it to the glass. Add two cherries, the bitters, and muddle. Pour in the simple syrup, one ounce of bourbon, and stir. Fill the glass with ice and add the remaining bourbon. Garnish with half an orange and a cherry.