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When it comes to high end cocktail bars, the dealer’s choice—an off-menu concoction fashioned by the bartender on the spot to suit a customer’s personal tastes—is far from novel. It’s been the lifeblood of countless swanky mixology dens the world over for decades, some going so far as to banish menus altogether in favor of these spontaneous creations, each order an attempt to foster a more intimate relationship across the pine. The concept is so common and pervasive that it’s almost become mundane. So why, then, has famously inventive Chicago chef-restaurateur Grant Achatz’s The Office, a handsome two-year-old speakeasy inside Columbus Circle’s posh Mandarin Oriental Hotel, an American Express Fine Hotels & Resorts property, managed to amass nothing short of a cult following with this seemingly simple boozy exchange? In short, they do things a little differently.

“The dealer's choice exists in the ether, exists for us all to enjoy together in a conversation,” bartender Jonah Dill-D’Ascoli told me on a recent visit, his voice tinged with the mystical whimsy of a whiskey-wielding oracle. “It’s us having a chat about what you're excited about, what you like about life, stories from your life, whatever you want to talk about.”

In most dealer’s choice scenarios, the barkeep will plainly ask the patron what spirits they prefer, if they normally like their drinks up or on the rocks, and possibly what flavor profiles appeal to them. Moments later, the patron is presented with a cocktail and a brief description of said cocktail. Usually, they are either variations on a familiar theme—a rum Old Fashioned with walnut bitters, perhaps, or a Rickey spiked with mezcal and sherry—or too obscure a recipe for a standard, everyday menu like the Johan Goes to Mexico (mezcal, lemon juice, simple syrup, and an entire half-ounce of Angostura bitters). But The Office, in true offbeat Achatz style, boldly breaks from this mold.

During our animated back and forth, I confessed to Dill-D’Ascoli that I was feeling a bit tired from battling the cold wind and spending the better part of the afternoon attempting to teach my newly-retired mother how to use DropBox. I also let it slip that I loved amaro and knew The Office had an unparalleled selection. He returned a few minutes later clutching an elegant stemless tulip glass stacked with thick ice cubes and brimming with a mahogany-hued liquid. It smelled like Christmas on a Hawaiian coffee plantation.

“This is coffee, banana, passion fruit, blueberry, and because you're excited about amaro, Amaro Dell'Erborista, which is a really cool Piedmontese amaro, plus some special bitters to give it a piny element, amongst various other things, and the base is rye,” he explained. “You seemed like you could use an uplifting coffee drink. Sun-grown coffee takes on a lot of tropical fruit notes, like bananas and passion fruit, while shade-grown coffee takes on dark fruit notes, so blueberries, that kind of thing. I was playing with those two tones because the coffee liqueur I used, Mr. Black, is very dry and baseline.”

The drink hit the spot, the rich depths of its roastiness quelling the fruit’s juicy brightness. It was warming and layered without being heavy or sleep-inducing, an ideal pre-dinner drink after a long winter’s day. And while my mood ring of a cocktail struck me as unconventional enough, I soon learned that The Office’s dealer’s choice could get a whole lot weirder.

“They do it all different ways,” said Erica Roney, a Senior Account Executive at the PR firm Bullfrog + Baum and one of my drinking companions that night. “It could start out more direct, like, ‘What do you like? What are you feeling?’ But then people say some ridiculous things. You can literally create a character, like, 'I'm feeling like I ride a unicorn to work everyday but I also have a dark side that I don't tell anyone about.' You’re messing with them, but they feed off it. And when they come back they're like, 'OK, I made you x-y-and-z and here's why.' There's an explanation that comes with it.”

Dill-D’Ascoli overheard our conversation and made his way back over to our corner of the bar to corroborate Roney’s story. “Somebody asked me one time, 'Can you make me a drink based on that wall right there?' It was fun,” he said with an easy smile.

Dill-D'Ascoli cheery demeanor, not to mention his willingness to entertain a wall-inspired drink order, stands in stark contrast to the stereotype of the snobbish, suspendered craft cocktail purveyor, quick to look down his nose at any vodka-sipping dilettante who dares saddle up to his hand-rubbed zinc bartop. This was a welcome surprise, especially considering The Office, on paper, practically screams exclusivity: The entrance is hidden inside the New York outpost of Achatz’s legendary Aviary, a tony molecular gastronomy-inflected restaurant complete with sweeping Central Park views, the backbar is chock full of rare and vintage spirits, many dating to pre-Prohibition, and curated cocktail flights like “The Macallan Experience” run several hundred dollars a person. Despite it all, The Office comes across as markedly unstuffy, a place where curious drinkers can dip their toes into liquor’s vast and varied waters without fear of sounding unhip, where the soundtrack jumps from Chance the Rapper to Billie Holiday while folks of all ages lounge about plump leather armchairs pairing century-old Chartreuse with crunchy chicharrones. Treating the dealer’s choice like an improv comedy exercise is a clever way of sustaining this quirky ambiance, proof that cocktailing can be at once artfully serious and utterly silly.

For round two, I knew I had to go all in. “I want a drink you would make for Oscar the Grouch on a rainy day,” I stated confidently.

“Poor guy, that's rough. I mean, he already lives in a garbage can and an ant is his best friend, and now it’s raining,” said Dill-D’Ascoli, pondering his assignment. “Let's be perfectly honest, he's got some things he's dealing with. But then again, maybe he's not necessarily in a bad mood. He's cozy, he probably feels better in the rain than most. It's in his nature.”

Dill-D’Ascoli turned his back to the bar and scanned the shelves. The Office’s cocktail program is heavily influenced by their unfettered access to dozens of interesting tinctures, syrups, and other housemade potions. Chef Achatz runs both of his Aviary locations (the original opened in Chicago in 2011) more like kitchens than bars. His wildly adventurous yet painstakingly precise cocktails are assembled by highly trained liquid line cooks and delivered to seated patrons by professional servers. Achatz’s culinary-esque approach demands a plethora of specialty ingredients more often found in fine dining restaurants than drinking dens. Subsequently, many of those ingredients end up infused into neutral grain spirits and funneled into the old fashioned medicine bottles lining The Office’s ample backbar.

“The thing about Oscar, I feel like he's a truffle guy,” said Dill-D’Ascoli, placing a sturdy rocks glass full of peculiarly-scented burnt orange liquid in front of me. “He's going to have that earthy, garbage-y funk about him but I also feel like he has expensive tastes, you know, despite the fact that he lives in a garbage can. It's like Warren Buffett—he lives frugally but he's secretly the billionaire of Sesame Street.”

“So it’s black truffle tincture, a touch of bitter artichoke liqueur, honey, Oloroso sherry, and three different types of rums: Dos Maderas, this a really cool Guyanese rum that they age for five years in PX Sherry casks, then Scarlet Ibis, which is kind of a funky blended rum, and then a touch of our well rum just to give it some dryness,” he continued. “It's cool right?”

Cool indeed. The honey provided a pleasantly sludgy mouthfeel, viscous yet velvety like fresh coconut water, while the sherry, truffle, artichoke, and rum formed a crashing wave of plump dried fruit, must, tobacco, and the sweet dank smell of a European wine cellar. It was gorgeous.

As Dill-D’Ascoli started in on the next customer’s prompt (“a drink that's about Harry Potter meeting Tinker Bell for the first time in an alternate universe”), I sat back and admired his handy work. It was undoubtedly one of the better cocktails I’d been served in recent memory, and as someone who drinks for a living, that’s saying something. Would I have asked for a garbage can-flavored cocktail under any other circumstances? Not a chance. Luckily, that was the hand The Office dealt me, and it was a winner.


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