Jackson Cannon | Bar Director, Eastern Standard, Island Creek Oyster Bar, The Hawthorne

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After graduating from Boston’s Berklee College of Music and beginning his career as a musician, Jackson Cannon realized his heart was in an entirely different place—he was more interested in the bars and restaurants he was performing at rather than playing bass. “It was almost like I played music to be a part of tavern culture,” says Cannon.

And with that, he dove full force into hospitality. In 2005, he opened Eastern Standard, one of Boston’s premier brasseries, and nearly 15 years later, he serves as Bar Director there and at Island Creek Oyster Bar, and is a partner at The Hawthorne. While all three entities are related, each has its own personality: Eastern Standard serves a wide range of drinks to accompany everything on their breakfast, lunch and dinner menus; Island Creek Oyster Bar “applies some filters,” says Cannon, focusing on aperitifs, vermouth, and Champagne, while The Hawthorne represents America’s Golden Age of cocktails during the late 19th century and pays tribute to New Orleans cocktail culture.

One of The Hawthorne’s most popular outputs is a drink known as the Phil Collins, “a really light, refreshing vodka drink that you could slip to a gin drinker, because it’s really subversive,” says Cannon. Of it’s creation, Cannon recalls, “It was a cute joke that ended up with us having a huge party every year for Phil Collins’ birthday.”

When he’s not creating new cocktails for his various programs, Cannon is constantly on the move, noting there’s typically only one month out of this year that he isn’t traveling. The rest of the time he’s heading directly to spirits suppliers, learning their stories to relay to his own customers, mentoring staff, and attending nationwide cocktail conferences.

So what does Cannon do when he’s not running off to New Orleans to attend Tales of the Cocktail for the fifteenth time? Here, he tackles our Lookbook Questionnaire to share his weirdest cocktail experiment involving bread, a trivia question he’s stumped on and the best thing he’s ever drank.—Tatiana Bautista

Current occupation:
Partner in The Hawthorne and Bar Director for our sister restaurants Eastern Standard and Island Creek Oyster Bar.

What do you want to be when you grow up?
An ad man.

Best thing you ever drank:
A warm pechuga coming off the still at Santa Catarinas Minas in Oaxaca. It just explodes with flavor. I had to sit down on the ground—tasting that haunting spirit at the source overwhelmed me in every way.

Worst thing you ever drank:
I’m not really that kind of guy. I don’t list things in my memory by bad experiences. Whatever it was, I’m over it.

First time you ever got drunk:
When I was almost 12 at my older brother’s wedding. There was a red wine and a white wine, and I kept mixing glasses of them together until they were pink—so ahead of my time. I still remember that first hangover, and the headache when the light hit my eyes the next morning.

If you had to listen to one album on loop, for the rest of your life, what would it be?
Pinkerton by Weezer.

What’s the weirdest hobby you currently have or have had?
I’m a Washington Redskins season ticket holder, and I live in Boston. It’s kind of silly, but it’s a family thing.

Weirdest cocktail experiment you’ve ever attempted:
I worked out this “Irish Breakfast” cocktail that had whiskey, egg, OJ, a little tea, honey and a slice of bread. When we made the drink at Eastern Standard, we’d muddle a slice of bread into two ounces of whiskey, and then strain that out to add the rest of the ingredients. Two ounces of whiskey went in, but only 1 1/2 came out…. So wasteful! But it wasn’t half bad. The team thought I was nuts, and for a couple of weeks the mise en place had sliced bread in it.

What’s your favorite thing to do when you’re not eating, drinking or drink-making?
Spending time with my kids—they are nine and 11. I recently made a list of the greatest PG-13 movies of all time and we’re working our way through it, one movie night at a time.

Weirdest drink request you’ve ever gotten:
It also might be the best—I was playing a playlist of mine and making drinks in service on a pretty quiet night and a guy walked up to me and asked me if I liked Leonard Cohen. When I replied that I did, he said, “would you mind creating a drink for me called the ‘Tower of Song’?” I made this long tall rye/ginger/honey drink (a riff off a Penicillin, really) but with layers like a swizzle.

Your favorite bar, and why:
Glass in Paris. Though it pains me, I haven’t been in a few years. Perfect mix of industry, neighborhood and just let your hair down good times. My photos from nights there are always real blurry…. Sometimes when my boy Josh is spinning, it gets so hot in there they have to run a shirt check for the men. God I love Paris.

Best meal you’ve ever had:
French Laundry. The best ingredients, creative execution, and every bite seems designed for your pleasure, not some kind of intellectual regard. Service and atmosphere just take you into the bubble. Happy place.

What’s your go-to drink in a cocktail bar?
DTO [Daiquiri Time Out], if I need some juice. Cognac Sazerac, if I need an Old-Fashioned.

Wine bar?
Chenin blanc.

In a dive bar?
Rum and Tonic. And shots, lots of shots…

Your preferred hangover recovery regime:
Avoid, with lots of water the night before. But day of, it’s all about respiration. If I can’t handle a run, a long walk in the woods with lots of electrolyte beverages.

The one thing you wish would disappear from drink lists forever:
“Fat Washed.”

The last text message you sent:
“Hey bro, really struggling with this trivia question and need your help! Name 4 schools that graduated a president and a Super Bowl winning QB. I got Stanford, Michigan, Navy but am stumped on the fourth!”