Add a sugar cube to the bottom of a rocks glass. Dash bitters over the top to begin dissolving the sugar.
Add the cherry and orange slice and continue muddling until the fruit is broken down and juicy.
Fill the glass with ice.
Pour brandy over ice, stirring to combine.
Decide whether you want a sweet, sour, or press old-fashioned:
Sweet: Top the cocktail with 7UP® or Sprite.
Sour: Top the cocktail with Squirt or Jolly Good.
Press (or dry): Top the cocktail with club soda or half club soda and half 7UP
Garnish with more cherries, olives, or cocktail mushrooms, however you prefer.
Enjoy immediately.