Robert Simonson didn't know cocktails would be his passion until he'd arrived at Tales of the Cocktail, the annual convention dedicated to all things shaken and stirred. Held every July in New Orleans, the day-drinking capital of the world, Tales is a half professional symposium, half adult summer camp for the globe's top bartenders and savvy spirits brand reps.

As a first step into the cocktail world, a trip to Tales is essentially like showing up at the Olympics with a bathing suit. To hear Simonson tell it, he went out of a combination of politeness and curiosity, invited by the event's organizer, Ann Tuennerman (then Ann Rogers), after a chance meeting in NYC. At the time a veteran theater journalist, he had recently started to feel burned out on the subject and had begun writing about wine as a way to break the monotony. “I always liked wine, and I always wanted to know more about wine, and I’d reached a breaking point of going into wine stores and looking at bottles and knowing nothing,” he says.

But wine turned out to be just a brief diversion, and it was the cocktails at Tales that changed the course of his career. Or rather, one cocktail: a Sazerac, the quintessential New Orleans classic that is not for the faint of palate. At the time, Simonson's cocktail knowledge was minimal—his first drink ever was a Sea Breeze (a.k.a., a vodka-cranberry with some grapefruit juice thrown in)—and the Sazerac's punchy, unapologetic mix of rye, absinthe-like Herbsaint, and Peychaud's bitters was a wake-up call. “There were flavors in there I had no experience with,” he says. “I loved it.”

“The odds are against bartenders at this point. So many drinks have been invented at this point that you brace yourself for disappointment. But you hope they’ll hit it out of the park.”

The drink came at just the right time. 2006 was riding the crest of the craft-cocktail revival—Tales was in its fourth year, and a wave of soon-to-be-iconic bars, including Pegu Club and Death and Co., had just opened around the country. A new class of bartenders were about to permanently change the way we drank, and Simonson was there to witness it all. His latest book, A Proper Drink, is an extensive history of that period, stretching from the mid-'90s to 2010. He maps out the key players and ideas that inspired this boozy revolution, drawing on more than 200 interviews with those who were there. 

It's a very different approach from his first book, published in 2014, which was a deep dive into the legacy of just one cocktail: the Old-Fashioned. Simonson is known to be focused in his passions both in writing and in person, and he remains loyal to the gin drinks and classic cocktails that he first fell in love with. Though he will always taste a bar's original concoctions—“When I’m out I sort of feel duty bound to try the original menu. The odds are against bartenders at this point. So many drinks have been invented at this point that you brace yourself for disappointment. But you hope they’ll hit it out of the park.”—he'll generally fall back on something tried-and-true. 

And you still can't pry him away from an Old-Fashioned. “It’s a winner every time.”

From a new-school Old-Fashioned, to a forgotten pre-Prohibition classic, these are the 10 drinks that made Robert Simonson's career.