1/2 cup ice cubes, or as desired
2 dashes bitters (such as Angostura®)
2 fluid ounces bourbon
1 fluid ounce orange-flavored liqueur (such as Cointreau®)
1 dash maraschino cherry juice (optional)
1 maraschino cherry
Fill 1/3 of a cocktail shaker with ice. Shake bitters over ice and pour in bourbon. Pour orange-flavored liqueur and maraschino cherry juice into shaker. Cover shaker and shake vigorously. Pour drink into a martini glass and garnish with maraschino cherry.