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!
👩🏻🍳 Tamara Talks – About Tootsie Roll Cocktails
Several months ago, I came across a tootsie roll cocktail in the Liquor.com 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
Here is a quick look at the ingredients in the recipe – it’s handy to use at the grocery store or as a summary of what you need. Skip to the recipe for quantities.
- 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.😀
- 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.
- Prepare garnishes.
- 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.
Is this a sweet cocktail?
Do I need to use expensive spirits?
🧂 Useful Stuff
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- modern martini glasses – These are the glasses you see in my photos.
- channel knife – This tool does a really good job of making long strips of orange peel.
- Mason cocktail shaker – I like this one for photos, but choose one with a good strainer.
- stainless steel jigger
- martini glasses – I love these glasses, and they’re far less likely to break!
- coupe glasses – As I mentioned above, I sometimes request “straight up,” and no ice. This is a well-priced and fairly sturdy coupe glass.
- chocolate bitters – There are other brands, and sometimes I use my homemade bitters.
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.
Tootsie Roll Manhattan
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- 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!
NOTE: Macronutrients are an approximation only using unbranded ingredients and MyFitnessPal.com. Please do your own research with the products you’re using if you have a serious health issue or are following a specific diet.