Jackson Cannon in action (Photo: Susanna Bolle)

“I was into drinking from a really young age,” says Jackson Cannon, who runs the bars at both the venerable Eastern Standard and its new sister restaurant, the Island Creek Oyster Bar. But don’t get the wrong impression. He’s not confessing to a youth spent in a haze of alcoholic excess. Cannon was into drinking before he had drunk much liquor himself. It was the rituals around cocktails, rather than the drinks themselves, that first captivated him: the storytelling of the toastmaster, more than the esoteric techniques and tools of the bartender or the occasionally arcane and mysterious ingredients.

“In my house, even before we drank alcohol, we were all in on the toast,” he explains. “And when my father took his gimlets in the summer, I would get a glass of sweetened lime juice, so I always liked the idea of drinks and drink-making and how that fit into a social context.”

Even Cannon’s introduction to what remains his favorite classic cocktail, the Jack Rose, came not in a glass, but in a book. When he was young, his father was reading to him from Hemingway’s The Sun Also Rises (Cannon is a great admirer of Hemingway) and, at one point, the narrator sits at a bar and orders a Jack Rose. The name itself was enough to pique his interest (Jackson. Jack. Enough said.) and his father, much to Jackson’s surprise, was with a little jog of his memory able to rattle off the basic ingredients: Applejack, lemon juice, grenadine. But it would be quite some time before the drink itself would live up to his expectations of it. Bottled grenadine, for one thing, was not going to cut it. You can learn more about Cannon’s quest for a proper Jack Rose from this 2006 article on the Jack Rose Society in Boston magazine.

Jackson Cannon (Photo: Susanna Bolle)

Oddly enough, in spite of his early interest in spirits, Cannon didn’t start tending bar professionally until relatively late. Bartending is his second career. Music was his first. He came to Boston to attend Berklee and then worked as a professional musician. When he did step behind the bar, he was fortunate to get in at the very beginning of Boston’s cocktail revival. He’d been the booking agent at the Lizard Lounge in Cambridge, when Brother Cleve, a legendary figure in both the local music and cocktail scenes, was running a lounge night there called Saturnalia, and Misty Kalkofen (now at Drink) was behind the bar. Soon the three began to explore  a wide variety of classic drinks. It was at that time that his curiosity about cocktails developed into something more serious.

“In the mid late 90s, I would wake up every day and wanted to learn more about food and about how bars and restaurants work,” he recalls. “I knew I wanted to pack up my bass and pick up the shakers and do it full time. People sometimes ask if I miss it and I say, ‘No! I write cocktail menus. I read cocktail books. I teach classes and get to teach young people to do what I love to do — I’m obsessed.'”

One of the finest expressions of Jackson’s cocktail obsession is the bar at Eastern Standard in Kenmore Square, which opened in 2005 and features a craft cocktail program on an epic scale. The bartenders there deal with an astounding volume of customers, particularly during Red Sox home games, but are somehow able to mix an extraordinary array of cocktails under intense pressure.

“It seemed a little zany at the time,” Cannon admits. “Even now when people visit five years later and it’s cruising, they remark on how we do the impossible, especially if they run a little 10-seat craft cocktail bar. And we put together a credible, top-tier craft cocktail for them, they just can’t connect the two. It’s not easy, it’s hard. And the young kids who come into the program really have to dedicate themselves to it, but the hard part was getting going. The hard part isn’t doing more volume. Sometimes volume is the answer, because you just get to practice. Not everybody wants a five-step egg drink, only some people do.”

When it opened five years ago, Eastern Standard’s cocktail list was comprised of just six drinks. In subsequent years, the number expanded to over sixty cocktails. This was in part due to the profusion of new liquors and the rediscovery of old ones (Rye, Genever, Old Tom’s Gin and the like), which makes the bartender’s work considerably more interesting. There’s also been a proliferation of small producers, which is something that Cannon admits he’s particularly passionate about.

Jackson Cannon (Photo:Susanna Bolle)

Making use of these boutique spirits is one of the focal points of the drink menu he’s put together at the new Island Creek Oyster Bar, which he sees as providing a rough analogue to that restaurant’s farm-to-table ethos. “Spirit production in general is about capturing the genie in the bottle. It’s taking something that’s big and concentrating it in another form, so it should still speak to how it was made and where it was made. In small production you get that — you get the equivalent of terroir.”

But, ultimately, it’s been the development of a new culture surrounding drinks and drink-making, rather than the greater availability of spirits, bitters and the like, that Cannon sees as the most exciting change since he started tending bar. “There’s this consciousness now that there’s this whole world of cocktails out there and the bartender is the expert,” he says. “For anyone who wants to tend bar for a living, it’s important to remember it’s all about service. You won’t survive long if that’s not in your head and in your heart, but these days, not only do you have all this stuff behind you at the bar, but you have people in front of you, who are willing to have you, the bartender, put it together for them. And that’s a change from ten years ago. That’s a big change. It’s a great time to be mixing drinks.”

When I asked him for a favorite cocktail recipe, Cannon offered two: a classic and a recent creation. It should come as no surprise that his classic cocktail of choice is the Jack Rose, made with fresh lemon juice, homemade grenadine, and a little Peychaud’s bitters. “That for me is the perfect drink,” he says. “It’s traditional with Applejack. It’s marvelous with Calvados. I’m not conservative. I’m pretty flexible with that sort of thing.”

Jack Rose

2 oz Applejack
3/4 oz homemade grenadine*
1/2 oz lemon juice
2-3 dashes of Peychaud’s
Shake well, garnish with lemon oil

* combine 2 parts pomegranate juice to one part sugar, cook slowly until syrup, and add a little orange blossom water (to keep it from being cloyingly sweet)

As he considers a more recent favorite, Cannon hesitates a moment before choosing. “This is kind of one of those things — don’t make me choose! But I’ll choose the drink I just made today. Tomorrow I may be past it, but today it is my obsession. And today’s drink is the Avignon.” Personally, I hope he doesn’t get past this obsession too quickly, since it’s a gorgeous drink. It’s an aperitif, currently available at Island Creek, that’s made with Small’s gin from Oregon (a gin with an unusually pronounced cardamom flavor), a bit of quince puree for a little pucker, and topped with champagne. “Now that’s the way to start your night,” he says.

The Avignon (Photo: Susanna Bolle)

The Avignon

3/4 oz Small’s gin
3/4 oz quince puree **
1/2 oz lemon juice

Light shake (with ice)
Strain into a cocktail glass and top with champagne.

** Slow poach quince with black peppercorns, bay leaf, a little bit of green cardamom, small amount of cloves, sugar, salt, and water. Let sit overnight, remove some of the fruit, puree and add more water as needed to get a syrupy consistency.