Pre-Prohibition Cool

I’m not sure if this one qualifies as a “famous” pre-prohibition cocktail, but it’s definitely from the prohibition era, if not sooner. As with most cocktails this old, the story of its origin is hazy at best. Wikipedia claims that there are two distinct theories:

  1. It was named by the Southside Sportsmen’s Club on Long Island
  2. It’s an homage to the South Side of Chicago.

Proponents of the latter story sometimes also claim it was Al Capone’s favorite drink – because his gang imported lower quality gin and they needed more sweetness to cover the rough edges. (As compared to the North Side gangs’ gin, which was apparently consumed with ginger ale.)

I’m not going to claim to know any better than Wikipedia, but I will say one thing: it’s a fairly straight forward “sour” style recipe, so it’s very likely that multiple bartenders in multiple places independently “came up” with a recipe similar to this one. It tastes good, so we all win!

By the way, if you’re looking for a lighter, fizzier variant, go ahead and strain into a collins glass and top with club soda. You just made a Southside Fizz!

Tools we Used:

You bet we used our own bar tools here! If you like, check them out on Amazon too:

Stainless Steel Boston Shaker

Price: $19.95

This is the best cocktail shaker you can buy – because we made it! Watertight and still easy to open, this is definitely our top choice.

Stainless Steel Hawthorne Strainer

Price: $16.99

South Side

South Side

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  • 2 oz Gin Traditionally Plymouth Gin, but we used another London Dry style.
  • 1 oz Lemon Juice
  • 5 leaves Mint
  • 1 oz Simple Syrup


  • Gently muddle the mint and lemon juice in a cocktail shaker.
  • Add remaining ingredients and ice.
  • Shake well.
  • Double-strain into a chilled coupe or martini glass
  • Garnish with lemon zest and / or mint