Cocktail & Other Recipes By Spirit Rye Whiskey Cocktails

Tootsie Roll

Tootsie Roll cocktail in a coupe, with a skewered cherry garnish balanced on the rim
Image: / Tim Nusog

The sweet, chewy, chocolate-flavored Tootsie Roll candy dates back to 1907. The Chicago-made treats are still a common sight in stores, and the individually wrapped versions find their way to the bottom of children’s outstretched bags each Halloween. But you don’t have to be a kid or wait for a special occasion to enjoy a Tootsie Roll, because drinks pro Aisha Sharpe turned the candy into an adults-only cocktail featuring rye whiskey, Pedro Ximénez sherry and lots of chocolate bitters.

The Tootsie Roll cocktail is a more serious affair than the name implies. Rather than relying on flavored vodka or chocolate syrup to achieve the desired taste, Sharpe enlists the intensely sweet, dark, dessert-like Pedro Ximénez sherry. The sherry is tempered by the spicy rye, and the bitters—made from organic toasted cacao nibs with just a hint of oak—impart chocolate notes into the drink without increasing the sweetness.

The cocktail is well-balanced, blending strong and structured whiskey with the rich PX sherry and the unmistakable taste of chocolate, while the Luxardo maraschino cherry garnish adds a final decadent touch. Make one for yourself the next time you want to drink down some childhood nostalgia.


  • 2 ounces rye whiskey

  • 1 ounce Lustau Pedro Ximénez sherry

  • 6 dashes Scrappy’s chocolate bitters

  • Garnish: Luxardo maraschino cherry


  1. Add the rye whiskey, sherry and chocolate bitters into a mixing glass with ice and stir until well-chilled.

  2. Strain into a chilled cocktail or coupe glass.

  3. Garnish with a Luxardo maraschino cherry.