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 rarely use white sugar to make simple syrup, preferring to use less refined sugar like this turbinado sugar syrup. We froze 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.
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.
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.
🧂 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
- 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.