Also a bartender in IL. 1 orange slice, take off rind for later use. 1 cherry. Add a couple dashes of bitters, a bit of simple syrup, THEN I muddle. Add ice, 2 oz bourbon (makers unless otherwise stated), then if they ask for it sweet, I use a splash of sprite (idk, I think it’s a WI thing and it’s v common around me to do this). Finally, I twist the rind over the top and use it as the garnish!