The Sling: The Simple Drink That Sparked Cocktail History
BIO
Leandro DiMonriva’s bartending journey began in the fast-paced world of Hollywood nightclubs, slinging AMFs and Incredible Hulks to a neon-lit crowd. But it wasn’t long before he found himself drawn to something deeper—the craft of classic cocktails. That turning point came at Cole’s French Dip in Downtown Los Angeles, where he trained under the legendary Brent Falco. It was there that Leandro’s passion for the art of bartending truly ignited.
Over the next decade, he honed his skills, studying alongside some of the most respected names in the industry and refining his knowledge of cocktail history, technique, and tradition. In 2017, he teamed up with producing partner Marius Haugan to launch The Educated Barfly on YouTube. They saw a gap in the market: while cocktail content was plentiful, few channels were led by working bartenders. Their solution? A show rooted in professional technique, rich history, and thoughtful storytelling—with the recipes to match.
Since then, The Educated Barfly has built a loyal following of over 600,000 across social media and collaborated with major brands like Sony, HBO, Luxardo, and Jack Daniel’s, just to name a few. Leandro continues to create engaging content across YouTube, Instagram, TikTok, and the official Educated Barfly website.
When we talk about the history of cocktails, people love a good origin story—something neat and tidy that gives us a sense of where our favorite drinks came from. It’s comforting to believe that each cocktail has a clear beginning, a specific person or place to credit. But the truth? It’s murkier than that. For much of their existence, cocktails weren’t seen as important enough to document. What we’re left with is a hazy blend of myths, half-truths, and speculation.
Most bartenders and drink historians like to kick things off with the Old Fashioned. And fair enough—it’s a big deal. It’s iconic, it’s delicious, and it still turns up on just about every cocktail menu. Plus, it’s one of the few drinks that actually aligns with the original definition of the word cocktail: spirits, sugar, water, and bitters.
But here’s the thing—and it’s a big one—
The Old Fashioned wasn’t the beginning. Not even close.
If you really want to trace the roots of the cocktail, you have to go back further. First, to Punch, the large-format social sipper. But since this book is focused on single-serving drinks, we’re skipping Punch and heading straight to the often-overlooked Sling—a drink that’s become little more than a historical footnote.
Let’s be honest: most modern drinkers don’t give the Sling a second thought. It’s not trendy, it’s rarely seen on cocktail menus, and its role in cocktail evolution is usually brushed aside. Some even argue it doesn’t qualify as a cocktail at all. It’s more of a rough-and-ready mix that came along before cocktails had even been defined. But here’s why that matters: without the Sling, cocktails as we know them today might never have existed.
Part of the reason the Sling is so underappreciated is that there’s not a lot written about it. A quick Google search won’t turn up much. Some sources claim it appeared in the late 1800s as a precursor to the Highball, but that doesn’t hold water. We have actual evidence that a “bittered sling” was around at least as early as 1806. That year, an Upstate New York newspaper, The Balance and Columbian Repository, published this definition of a cocktail:
“A stimulating liquor composed of spirits of any kind, sugar, water, and bitters. It is vulgarly called a bittered sling and is supposed to be an excellent electioneering potion because it renders the heart stout and bold, at the same time that it fuddles the head.”
Now that’s a quote.
That one line tells us two things. First, people have always used alcohol to get courage and lose inhibition. Second, if a “bittered sling” was already a known variation, then the unbittered Sling must have come first.
It likely began in the early days of American distillation—maybe even earlier—as a way to make rough, often barely drinkable spirits more palatable. Back then, distilling was a crude science. Spirits were harsh, hot, and heavy with impurities. So what did people do? They added water to cut the burn and sugar to soften the taste. Boom—you’ve got yourself a Sling. A simple, effective little concoction that made bad booze go down a whole lot easier.
And if you’re like me, someone who loves to understand where things really begin, this is gold. The Old Fashioned didn’t spring into existence out of nowhere—it evolved. And though the most popular origin stories for it have been debunked (shoutout to David Wondrich for doing the detective work), the bigger truth remains: early drinks like the Sling paved the way.
In fact, when you look at the drinks that came after it, you can see the Sling’s fingerprints all over them. It was the prototype, the patient zero of cocktails. Without it, the entire family tree of mixed drinks would look very different.
The Sling is also wonderfully flexible. You can make it with just about any spirit. Its structure wasn’t rigid or precious. It was practical. Today’s cocktail culture can sometimes be a bit obsessed with precision—recipes measured to the milliliter, techniques dialed in to the decimal. But the early days? They were looser, more about function than form. That flexibility gave birth to a whole world of drinks. It was messy, sure—but it was also how progress happened.
So what exactly was a Sling?
Historically, it was served in a tall glass, diluted with a good amount of water. The bittered sling—the one referenced in that 1806 quote—was a clear stepping stone toward what would become the Whiskey Cocktail and eventually, the Old Fashioned. Wondrich notes that back in the 1800s, the only real difference between a Sling and a Toddy was that the Sling was garnished with grated nutmeg. That’s it. Both drinks could be served hot or cold, and both leaned heavily on water to tame the fire of rough spirits.
For this recipe, I’ve adapted the Sling to resemble something closer to the Old Fashioned. We don’t really need to “proof down” harsh spirits anymore, so the water element is minimized. But the heart of the drink remains.
Understanding where the Sling fits in cocktail history isn’t just about trivia—it’s about seeing how one humble, scrappy little drink helped shape an entire craft. It reminds us that cocktails weren’t born in a flash of inspiration—they grew, changed, and evolved. Just like any good story.
And it all started with the Sling.
Bittered Sling
Ingredients
2-3 Dashes Angostura Bitters
1 tsp Caster Sugar
1oz (30ml) Water
2oz (60ml) Old Tom Gin
Orange Twist (optional)
Directions
Add bitters, sugar, and water into A Double old-fashioned glass. Muddle lightly to crush sugar and combine the ingredients. Next, add in Old Tom Gin with a Big Rock of Ice. Stir lightly to chill. Serve with an Optional Orange Twist.
