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.

I grew up in Wisconsin, a state of proudly provincial culinary peculiarities. For instance, a brandy Old-Fashioned, not a typical whiskey Old-Fashioned, begins the meal at every supper club. And at Christmastime, mugs of Tom and Jerry are handed around. This is the Badger State version of yuletide cheer. I grew up thinking everyone in the country spent Christmas downing cups of the hot, creamy, liquor-laced beverage. Later I discovered that the upper Midwest was one of the few areas in the country to hang on to the once-popular 19th-century drink. Did the tradition inspire in me a latent interest in drinking history? It’s not impossible.

In my young adulthood, my drinking habits were pretty plebian. I was content with my Cape Codders. The woman I was dating at the time was having none of that. At the SoHo Wine Bar on West Broadway, a hot spot in 1991, she cut me off mid-order and informed the bartender that I would be having a gin Gibson. I’d never had one before then and it was a revelation. I felt wonderfully elegant sipping on it, and was surprised by the subtle, but distinctive difference the addition of a cocktail onion made. I learned something about the dignity of cocktails that evening. I’ve been drinking Gibsons ever since. 

“She’s got a peaty finish!” So said the garrulous rummy at Pete’s Waterfront Ale House, a Brooklyn tavern with an above-average whiskey selection for the time. Imagine that line delivered with a roguish Scottish burr. He was talking about Lagavulin, the single malt Scotch made on the island of Islay. I didn’t know what Lagavulin was, let alone how to pronounce it. But I was intrigued. I moved on from Lagavulin to Oban to Talisker and other single-malt Scotches. An education in whiskey had begun. 

During the late 1990s, a college friend of mine got a job in England. She and her husband, Jon, lived in Wimbledon for a couple of years. In 1999, while on a business trip, I took the long Tube ride to their home and spent a leisurely afternoon with Jon drinking in their spacious backyard. He went on and on about having been converted to a cherished local liqueur. I thought he’d gone balmy and humored him, drinking a glass or two of the red stuff and dutifully complimenting the drink. That was my first exposure to the deeply English gin liqueur Pimm’s No. 1. Jon, it turned out, was right; I was the balmy one. As the cocktail revival got in gear during the '00s, I watched Pimm’s become embraced by U.S. drinkers.

In 1999, I took my first trip to Amsterdam. There, I stayed with a friend, an expatriated American who had married a Dutch man. To say he enjoyed drinking was putting it mildly. The port decanter was always full and he had a way with making a Mojito. On my last day, he led me down a dark passage off Dam Square to a tiny, wooden drinking den. The place was dark as night and as old at time. There we drank something called genever from small tulip-shaped glasses. The vessels were filled to the brim and tradition commanded you bend over the glass, hands behind your back, to take the first sip. The drink was delicious; the ritual charming; the bar fascinating. Wynand Fockink was more than 300 years old and made many of its own elixirs. Here was a world unto itself, well worth inhabiting. 

The Sazerac is the drink that changed my career, and my life. Prior to 2006, I was primarily an (unhappy) theater journalist, trying to transform myself into a wine writer. Then I was invited, on a whim, to attend Tales of the Cocktail, a new cocktail convention in New Orleans. My first drink in that city was a Sazerac at the rotating Carousel Bar inside the Monteleone Hotel. I had heard of the Sazerac, but never had one. The name sounded weirdly exotic, as did the ingredients. I had never tasted any drink made with rye whiskey, Herbsaint or Peychaud’s bitters—let alone all three of them together. I took one sip and the world stopped (though the bar didn’t). I’d never sampled a mixture so complex and bewitching. Upon return to New York, I shifted my writing focus to cocktails and spirits and never looked back.

One of the first seminars I attended at my inaugural Tales of the Cocktail was held by a scientist named Ted Breaux. It was about the history of absinthe, a liqueur I mainly knew from paintings by Impressionists like Edgar Degas. I assumed the talk would be purely academic, as I understood the green, high-proof spirit to have been long ago banned in the U.S. I was astounded then when he began pouring out samples of absinthe he had distilled in France. "That’s springtime in a bottle!" he exclaimed. The whole affair seemed illicit and dangerous and wonderful; I half expected the cops to raid the room any moment. This cocktail/spirits thing has a history and mystery to it I hadn’t anticipated. Thereafter, I grew used to tantalizing discoveries in the pursuit of my new beat. 

In the early years of the cocktail renaissance, every mixologist, enthusiast, and drinks journalist took up a pet pre-Prohibition cocktail or two—an obscure mixture they chose to celebrate, extol, and keep an eye out for. For whatever reasons, the Monkey Glad was that for me. That is was a gin drink made it legit. That it required a touch of absinthe made it cool. That it was from Barflies and Cocktails, a recipe book published in Paris in the 1920s, rendered it romantic. When I saw it, I ordered it, and felt very knowing. The cocktail world was all about secret knowledge back then. I miss that time.

I went to Cure in New Orleans in 2009 because it was the hot new joint in that cocktail-loving city, as well a piece of free-standing mixology modernity in a sea of century-old restaurant and hotel bars. I left thinking differently about how cocktails could taste. The Art of Choke used a full ounce of Cynar as part of its split base. Up until then, I’d only ever encountered the bitter amaro in trace amounts within cocktails. There were a lot of upside-down drinks like that on the Cure menu, full of Campari and Peychaud’s bitters and such. As I walked out, I noticed a slim recipe book for sale, called Rogue Cocktails. It contained recipes for all these radical libations. To my everlasting regret, I didn’t pick up a copy. (Only 277 were printed. They are now collector’s items.) Bartenders the world over now embrace amari and bitters as a matter of course. Back then, though, their use was a radical innovation.

When Prime Meats opened in Carroll Gardens, Brooklyn, in 2009, an Old-Fashioned made with homemade pear bitters (from a pear tree in the back year) topped the cocktail list. The drink, served over a single, crystalline cube, looked beautiful and tasted even better. I asked the barman, Damon Boelte, if they sold many of them. Tons, he said. It was their most popular drink, particularly among twenty-somethings. A light switched on. In the weeks thereafter, I noticed old-school, non-fruited Old-Fashioneds popping up on menu after menu. At each place, the drink was selling like hotcakes. The Old-Fashioned, long misunderstood and associated with older drinkers, was back in, yes, fashion. I pitched the story to the New York Times. It became my first of many cocktail articles for the newspaper. Soon after, I sold the idea of a book-length look at the Old-Fashioned to Ten Speed Press. The volume—my first cocktail book—came out in 2014.