Tootsie Roll Cocktail

Think of this Tootsie Roll Cocktail as a chocolate manhattan (I do!)… Oloroso sherry, bourbon (rye, or scotch), generous amounts of chocolate bitters, and an orange twist combine to make a cocktail that is definitely reminiscent of the classic tootsie roll. If your well-stocked bar contains a good dry sherry, a blending whiskey, and chocolate bitters, you’ll have this super sipper ready in less than 5 minutes!

Two tootsie roll cocktails on a slate tray with orange peel twist.

👩🏻‍🍳 Tamara Talks – About Tootsie Roll Cocktails

Several months ago, I came across a tootsie roll cocktail in the newsletter, and it piqued my curiosity. Their version is rather sophisticated – rye whiskey, Pedro Ximénez sherry (a sweet dessert sherry), chocolate bitters, and a Luxardo cherry. As I’m always quick to mention, I do not love sweet cocktails, but I do love sherry, whiskey, and chocolate!

Thus began the experimentation… I wanted to create an off-dry cocktail that whispered of a tootsie roll. Confession: I have not had a tootsie roll in years! However, they were a childhood favorite, and I have not forgotten their chewy flavor.

In doing an online search, I came across a few tootsie roll cocktails that are essentially “candy cocktails” using ingredients like root beer, orange juice, chocolate vodka, and Kahlua. While those ingredients work for some, that was not what I was looking for. Since we always have bourbon, a drinkable dry sherry, and Aztec chocolate bitters, that’s where I started. The process of “getting it right” was not immediate, and one can only drink so many cocktails. Lol.

In the end, I landed on our usual blending bourbon, Emilio Lustau ‘Rio Viejo’ Oloroso Seco Sherry, and a generous amount of Aztec chocolate bitters. I do love bitters, and I’m never stingy with them in my cocktails. In fact, they’re a major player in my aguardiente cocktail. I recently tried this cocktail out on my favorite uncle visiting from California, and it’s his new favorite! I think it’s nicely balanced, and barely off-dry.

What is “oloroso” sherry?

Why did I choose oloroso sherry? I love the full-bodied, nutty, smooth, complex flavor. It works really well with the other ingredients. If you have a favorite sherry, that might be a great place to start. I do specify a little bit of simple syrup to bring out the chocolate notes in the cocktail. If you’re interested in sherries, see Which Sherry is Right for You?

📋 Cocktail Ingredients

Ingredients for the chocolate manhattan variant - Simple syrup, Aztec chocolate bitters, Evan Williams blending bourbon, turbinado simple syrup, and an orange.
  • sherry – I specify a dry sherry. If you prefer sweet cocktails, you can use a sweeter sherry, or add more simple syrup. We really like oloroso sherry in this cocktail, but we have used a fino sherry as well. See Which Sherry is Right for You? for more information.
  • whiskey – bourbon, rye, scotch, blended
  • chocolate bitters – Aztec chocolate bitters
  • simple syrup – I always make my simple syrup. See How to Make Simple Syrup … it’s quick and easy! You can buy simple syrup online, but it only takes a few minutes to make. We freeze the leftover syrup in ice cube trays for future use.
  • orange twist – My husband loves chocolate and orange together, and the orange twist garnish is in his honor. You can use a Luxardo cherry, but please don’t use a regular maraschino cherry.😀

🔪 Instructions

Step 1 - Equipment and ingredients assembled for the bourbon and sherry cocktail including a peeled orange.
Step 1 – Assemble equipment (cocktail shaker, bar spoon, jigger, garnishing knife) and ingredients (bourbon, sherry, simple syrup, chocolate bitters, and orange)…
  • Gather ingredients and equipment. You’ll need a cocktail shaker, bar spoon, jigger, garnish knife (optional), whiskey, sherry, simple syrup, chocolate bitters, and any garnishes you plan to use.
The cocktail ingredients with orange peel twisted for garnish.
I use a garnish knife to make long strips of orange peel (without pith) for cocktails. I then wrap the strips around chopsticks. It works!
  • Prepare garnishes.
A cocktail shaker with ice, tootsie roll cocktail ingredients, and a bar spoon.
Stirred not shaken! Strain into cocktail glasses either over a cube or not…
  • Add all liquid ingredients to a shaker with ice. Stir vigorously. Place the strainer cap on the shaker, and strain into chosen glassware. I sometimes use a coupe with no ice, and sometimes I use my pretty stemless martini glasses with a big square ice cube.
A close up of 2 angular cocktail glasses with an ice crube, the sherry and bourbon cocktail, and an orange twist.
I think this cocktail qualifies as a “Manhattan variant.” Here we see 2 completed cocktails with orange twist garnish!


Is this a sweet cocktail?

NO! If you’re looking for a sweet cocktail, you need to keep looking. I do not love sweet wine, sweet cocktails, or even most sweets. As a dark/bittersweet chocolate lover, this hits the right flavor notes for me.

Do I need to use expensive spirits?

No. We use a “blending” or “mixing” bourbon. We occasionally enjoy sherry straight, so we use an oloroso or fino sherry because we like dry sherries. You can substitute styles and brands that you like.

Note: As an Amazon Associate I earn from qualifying purchases at no additional cost to you. This helps to offset the costs of maintaining my blog and creating awesome content! 😊

Cocktail creation is fun for me… It’s a little bit like creating food recipes. This tootsie roll cocktail was fun. If you like dark, bittersweet chocolate, I think you’ll like it.

Signature in red and green with chiles and limes. Healthyish Latin cuisine.

2 modern, angular martini glasses with the chocolate Manhattan variant garnished with orange twist.

Tootsie Roll Manhattan

This chocolate Manhattan variant is reminiscent of a childhood favorite – the tootsie roll – while being off-dry and sophisticated!
5 from 1 vote

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Prep Time 5 minutes
simple syrup 30 minutes
Total Time 35 minutes
Course Beverages
Cuisine American
Servings 1 cocktail
Calories 175 kcal


  • 1 teaspoon simple syrup - see Post for more
  • 2 ounces whiskey - bourbon, rye, or blended
  • 1 ounce dry sherry - oloroso or fine; see Post for more
  • 10 shakes chocolate bitters - yes, it's generous!


  • Combine syrup, whiskey, sherry, and bitters in a shaker with ice.
  • Stir vigorously.
  • Strain into a cocktail glass, and garnish as desired. Enjoy!


Serving: 1cocktail | Calories: 175kcal

NOTE: Macronutrients are an approximation only using unbranded ingredients and Please do your own research with the products you’re using if you have a serious health issue or are following a specific diet.

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