Southside Cocktail

Said to be Al Capone’s favorite cocktail, this mixture of gin, lemon and mint just might be untouchable.

Southside Cocktail

It was cold night in New York City, and I didn’t want to go out. But my friend convinced me. We hailed a cab and took that yellow box all the way downtown, to a little hot dog joint that didn’t have a name. Inside was an old, broken phone booth that we squeezed into. My friend picked up the phone, muttered something I couldn’t hear… and seconds later a secret door in that old phone booth opened, revealing a 1920s style speakeasy hidden just beyond.

The drink I had that night was called the Southside Cocktail, a tangy and refreshing mixture of gin, mint, lemon juice and simple syrup. The barkeep that night was playing up the history for us, telling me that I was drinking Al Capone’s favorite drink. I was intrigued. What’s the story behind this cocktail that’s around a hundred years old? Did it involve gangland murders, shootouts with Eliot Ness or escapes from Alcatraz?

Turns out, the gangs on the Northside of Chicago had a nice, smooth gin that they were able to sneak in under the law’s nose. They drank their spirit with ginger ale, but Capone’s crew on the Southside could only get their hands on a rougher gin that was a little tougher to drink. In order to enjoy that ill-gotten booze, they had to mix lemons, mint and sugar with it. The Southside Cocktail was born.

Years later, whenever I muddle up some mint and shake myself a Southside, I’m glad the gin we use in it doesn’t get made in a bathtub anymore.

Muddling your mint?

Something to consider when prepping the mint for your Southside Cocktail: Breaking the sprigs up too much will make your mint taste bitter, giving your drink a slightly sour taste, and not the good kind. Start off softly, gently breaking apart the leaves to release the oils. The first time I muddled, I overdid it. The second time, though, was just right.

What is the best gin to use for a Southside Cocktail?

Because of Prohibition, folks that went to enjoy a few drinks at their local speakeasy were often served bathtub gin, which didn’t have the best taste. Since we don’t have to settle for bootleg spirits anymore, a good London Dry will not only taste great but also pack the right punch for this historical drink.

Southside Cocktail
Servings 1
5 minutes


  • 2 ounces gin
  • 1 ounce simple syrup equal parts sugar and water dissolved together
  • 1 ounce freshly squeezed lemon juice
  • 5 fresh mint leaves plus an extra sprig for garnish
  • Ice cubes


  • Place the mint leaves in the bottom of a cocktail shaker, pour in the lemon juice and muddle gently using a muddler or the back of a spoon. Be careful not to over-muddle, as this can make the mint bitter.
    Southside Cocktail
  • Add the gin and simple syrup to the shaker with the muddled mint and lemon juice. Fill the shaker with ice, secure the lid, and shake vigorously for about 15 seconds.
    Southside Cocktail
  • Double-strain into a chilled cocktail glass, using a fine-mesh to catch any small mint pieces or ice shards.
    Southside Cocktail
  • Garnish with a mint sprig (you can clap it between your hands to awaken the aroma).


Calories: 217kcal | Carbohydrates: 23g | Protein: 0.3g | Fat: 0.1g | Saturated Fat: 0.02g | Polyunsaturated Fat: 0.04g | Sodium: 19mg | Potassium: 77mg | Fiber: 0.5g | Sugar: 21g | Vitamin A: 214IU | Vitamin C: 13mg | Calcium: 18mg | Iron: 1mg
Southside Cocktail

FAQs & Tips

Southside Cocktail

Southside Cocktail Variations

The Southside Cocktail has few different versions that’ll keep your tastebuds busy, as well as a few distant relative drinks you can check out, some of them right here at Twist and Toast.

  • For a Southside Fizz, simply top off your Southside Cocktail with soda water. If you’re feeling a little fancier, you can make a Southside Royale with champagne or your favorite sparkling wine.
  • Another drink you might enjoy is the Classic Daiquiri, which I write about here, and use rum as its base instead of gin.
  • We mentioned the Gimlet earlier, but have you ever tried a French Gimlet? St. Germain makes that drink a special one, which I talk about here.

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