The Southside: A Complete History & Classic Recipe

Summer in Chicago, 1920s. Jazz seeps from a hidden doorway behind a grocery storefront. A man in a crisp suit leans across a marble bar and whispers his order — gin, lime, sugar, and mint. The bartender shakes quickly, strain, and slides over a frosted glass glowing pale green under dim light. The air smells like citrus and crushed mint.

The drink is fresh, smooth, and quietly subversive. This is the Southside, a cocktail that carried the cool confidence of Prohibition’s speakeasies and the sharp elegance of gin culture’s golden age.

Part mojito, part gimlet, part Chicago myth — the Southside is the forgotten bridge between the roaring speakeasy and the modern craft cocktail. Its story is one of gangsters, golf clubs, and America’s complicated romance with gin.

I. Origins

Few cocktails wear their mythology as proudly as the Southside. Its origin stories split between two worlds — Chicago’s rough-and-tumble South Side of Prohibition-era lore, and the genteel lawns of New York’s private clubs.

The Chicago Story

The most popular tale claims the Southside was born in Chicago’s South Side district during Prohibition (1920–1933). Bootleg gin, often harsh and poorly distilled, needed softening. Bartenders (and occasionally mobsters) mixed it with mint, lime, and sugar to mask its rough edges. The result was smooth, refreshing, and surprisingly sophisticated.

Some accounts tie it to Al Capone himself, whose gang operated out of the South Side. Capone’s gin — reportedly inferior to his rival’s North Side distillate — inspired bartenders to disguise its bite with mint and citrus. Hence, a “South Side” cocktail.

The New York Connection

Another lineage places the Southside at the South Side Sportsmen’s Club of Long Island — an exclusive 19th-century retreat for New York’s elite. Their version likely used high-quality gin and fresh mint, closer to a refined julep than a bootleg fix.

Both theories hold truth: the Southside likely existed in some form before Prohibition, but Chicago’s underworld gave it attitude — and its name.

II. Historical Evolution

The Southside’s DNA is pure cocktail lineage. Structurally, it’s a gin sour with mint — a cousin of the Mojito and a sibling of the Gimlet. Its earliest printed appearances date to the 1910s and ’20s, but its true cultural resonance came post-Prohibition, when gin reasserted itself as America’s preferred spirit.

The Club Era (1930s–1950s)

By mid-century, the Southside had become a staple of East Coast country clubs and urban lounges. Served “up” in a coupe or “long” with soda water, it was the elegant antidote to whiskey-heavy bar menus.

The Southside Fizz, a tall version topped with soda, became especially popular in the Hamptons, where it remains a summer essential.

The Modern Rediscovery (2000s–Today)

As the craft cocktail revival took hold in the early 2000s, bartenders rediscovered the Southside’s effortless balance and classic structure. Fresh mint and gin — once maligned as old-fashioned — suddenly felt timeless again.

Today, the Southside sits comfortably alongside the Martini and Negroni as one of the definitive gin classics, bridging Prohibition history and modern craft simplicity.

III. Ingredients & Technique

The Southside may seem simple, but balance is everything — it’s the interplay of mint, citrus, sugar, and botanicals that defines it.

Core Components:

• Gin: London Dry or New Western; the gin’s character dictates the drink’s style.

• Citrus: Fresh lime juice (or lemon, depending on the tradition).

• Sweetener: Simple syrup — just enough to soften the edges.

• Herb: Fresh mint — the Southside’s unmistakable signature.

The secret: Don’t muddle the mint aggressively — a gentle press releases oils without bitterness. And shake hard — you want a silky texture and bright aromatics.

IV. Cultural Significance

The Southside is more than a refreshing gin cocktail; it’s a cultural snapshot of America’s shifting tastes.

In the 1920s, it reflected rebellion — gin made palatable during the nation’s great experiment with abstinence. In the postwar years, it symbolized sophistication — the cocktail hour polished and preppy.

By the 2010s, it came to represent a new minimalism in mixology: few ingredients, perfectly balanced, served with respect for craft and heritage.

Its dual identity — gangster and gentleman — makes it uniquely American. It’s both Chicago street and Long Island estate, jazz bar and golf club veranda. Few drinks embody class and contradiction so gracefully.

V. How to Make the Classic Version Today

Recipe — The Classic Southside

Ingredients

• 2 oz (60 ml) London Dry gin

• ¾ oz (22 ml) Fresh lime juice (or lemon juice for a brighter style)

• ¾ oz (22 ml) Simple syrup (1:1)

• 6–8 Fresh mint leaves

Method

1. In a shaker, gently press the mint leaves with simple syrup (do not muddle harshly).

2. Add gin, lime juice, and ice.

3. Shake vigorously for 10–12 seconds.

4. Double-strain into a chilled coupe or cocktail glass.

5. Garnish with a fresh mint leaf.

Specs

• Glass: Coupe or cocktail

• Ice: None (served up)

• Garnish: Single mint leaf or small sprig

• Style: Gin sour with mint

Technique Notes

• Use fresh, aromatic mint — spearmint works best.

• Avoid over-muddling; bitterness ruins the drink’s balance.

• For a taller version, strain into a highball with ice and top with soda water (the Southside Fizz).

Variations & Lineage

• Southside Fizz: Topped with soda water — refreshing and lighter.

• Northside (modern): Swap gin for vodka, popular in contemporary clubs.

• Clover Club’s “Green Gimlet”: A lemon-based version using mint syrup instead of fresh leaves.

Service & Pairing Tip

• Perfect aperitif or warm-weather cocktail.

• Pairs beautifully with seafood, garden herbs, or Mediterranean appetizers.

VI. Modern Variations & Legacy

The modern Southside has become a litmus test of bartender skill: can you balance mint and gin without either dominating?

Craft bartenders often tailor the gin to the drink’s intent — London Dry for structure, New Western for floral nuance, or navy strength for boldness. Some infuse the simple syrup with mint instead of shaking it fresh, achieving consistent flavor without chlorophyll bitterness.

The Southside Fizz has become a brunch and patio staple, while upscale cocktail bars serve the classic coupe version as a refined, minimalist expression of gin’s elegance.

Ultimately, the Southside endures because it’s timeless and flexible. Whether whispered over jazz or sipped poolside, it retains its effortless charm — refreshing, fragrant, and faintly rebellious.

“The Southside is what happens when bootleggers meet botanicals — and somehow, both win.”