It's 8 p.m. on a Friday - the magic hour in weekend parlance - and Eastern Standard bar manager Jackson Cannon is multitasking like an octopod.
Working the back end of the restaurant's lengthy bar, the bespectacled Cannon moves unflappably between tasks: ringing up tabs, directing his staff, and checking IDs with flattering casualness. During a spare moment, he comes out from behind the bar to hail regulars with a backslap and a hearty greeting. A couple inquires about his new baby, Abbey, and Cannon obliges with a flip through a pocket photo album.
And then, he goes back to mixing drinks. Apportioning ingredients with double-ended cocktail measures, Cannon transfers his concoctions to a shaker and mixes them with the rhythmic precision of a maracas player. As he works, he chats with customers about the benefits of bitters or the almost criminal devaluation of vermouth. Many are content to let Cannon be their shepherd.
"I put my faith in you, Jackson," a patron says, letting Cannon pick his drink for him.
That trust reflects Cannon's status as perhaps the city's most in-demand bartender. A traditionalist with a flare for invention, Cannon's made it his mission to revitalize people's faith in old-time elixirs, making devotees of the business types, scenesters, and Red Sox fans who frequent the Kenmore Square establishment, recently anointed one of the best bars in America by Esquire magazine. He's equally dedicated to customer service: In Cannon's world, happy hour is a holistic experience.
"He is a serious mixologist, but he's also a seriously service-oriented professional," says Lauren Clark, the founder of DrinkBoston.com. "Anyone who's serious about cocktails in Boston is going to go to that bar and learn something."
Always had a knack
"I have had a great love of alcohol since I was 8 years old." Drinking coffee during a rare moment of calm one afternoon, Cannon makes this proclamation with the utmost sincerity. After a few mischievous beats, he clarifies.
"I remember early on, my father would take a gimlet of Tanqueray gin and Rose's Lime, and I would take a gimlet of Rose's Lime, and we would have a cocktail and play chess," Cannon says. (His father is longtime White House correspondent and famed Ronald Reagan biographer Lou Cannon.)
But Cannon's path to the bar was circuitous. The Washington, D.C., native bypassed the family profession - his brother Carl is also a journalist - and came to Boston in 1986 to study music at Berklee. Cannon then spent the next two decades playing bass with various bands, traveling the world and working as a booker at local clubs like Toad and the Lizard Lounge.
He was living a good life - just not the right one for him.
"A time came when I just didn't feel that every morning, when I got up, I wanted to play," he says. Instead, the food industry beckoned. "I found that I was reading about food and reading about drinks and obsessing about drink-making."
Nearing 40, Cannon immersed himself in the restaurant world. He bartended, catered, even put in some time as a prep cook at Tremont 647.
"I was trying to give myself a roundsman's education in the business," he says.
It was Tremont 647 owner Andy Husbands who told him about a new venture in Kenmore Square. Before long, Cannon found himself in front of Eastern Standard owner Garrett Harker interviewing for the bar manager position - an interview that Cannon walked out of sure he'd bombed.
Harker recalls the exchange differently.
"I interview a lot of young kids, but Jackson had a sort of reserve about him," he says. "He's also got zealotry. He loves to read, and he's so culturally aware. It was an easy decision."
From the get-go, Cannon's vision for the Eastern Standard bar was ambitious: Elevate the art of drinking in a town once ridiculed for its provincial imbibing habits.
"You need to be fresh, you need to have quality, you need to have the historic component, and you need to push the envelope," Cannon says. He spent two months perfecting drink recipes, stocking up on top-shelf spirits, and immersing his staff in the history and art of mixology. When Eastern Standard opened in 2005, Cannon debuted a six-cocktail drink menu alongside the wine and beer lists, featuring such potables as the Whiskey Smash (bourbon, lemon, mint) and the Au Provence (a vodka-based gimlet).
Reaction, at first, was tepid. Opening two days before the Red Sox home opener, with its attendant crush of beer drinkers, didn't help matters. But Cannon and his staff pushed on, gently nudging customers out of their comfort zones - or as he puts it, "Striving to say yes, but sometimes saying yes in another way."
"That equation was my life for the first three or four months we were open," Cannon says. "Someone orders a second cosmo, you ask them if they've ever had a Jack Rose. Part of our subtext was to force a dialogue between the customer and the server."
There was another "must" to his approach: Place a premium on customer service.
"This is a business, and it's a competitive business. But what is a business? It's empathy," Cannon says. "As intimidating as the menu can be, the way we serve people has an incredibly approachable component."
DrinkBoston.com's Clark recalls the time a few years ago when, after spending time at the Eastern Standard bar, she decided to head over to another watering hole. Cannon offered to call ahead for her. "I really thought he was joking, but he was dead serious," she says. "I think it's his mission to bring back this old style of service that went away for a long time."
Now, just three years into his tenure, Cannon has achieved his goal of a hands-on drinking destination. His success can be measured not only in crowds - on Patriot's Day this year, the bar was five people deep at 8 a.m. - but also in the days' tallies: On a recent weekend night, the restaurant rang up orders for 274 different drinks. The cocktail menu now boasts 64 concoctions, from chest-hair-growing classics to raw-egg oddities to ambrosial, alcohol-free "mocktails." Cannon has fostered an audience for all of it.
"The thing that amazes me about Jackson is that he's just so professional," says Tony Espy, a loyal Eastern Standard patron who cheerfully blames Cannon for his Belgian beer-drinking habits. "He takes it really seriously. It's a career, and it shows."
Cannon's schedule is brutal: 18-hour days, 100-hour weeks, and little weekend rest for the weary (Luckily, his wife, Elizabeth, also works at Eastern Standard). When he's not on floor duty, he's often traveling for work, such as a recent jaunt to Kentucky to source exclusive bourbon from a small local distillery. Espresso helps, as does the Zen he achieves while working behind the bar. He's not complaining.
"Who gets into bartending and then bemoans working hard?" he asks. "I love it. My waking life is a dream come true."