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Darryl Chan: A Portrait of a Bartender

In the heart of New York City, where life often moves at a dizzying pace, there’s a place where time seems to slow down: The Portrait Bar at The Fifth Avenue Hotel. Recently named one of Esquire’s Best Bars in America for 2024, the bar has quickly become a standout, much in part due to the vision and virtuosity of Darryl Chan, The Fifth Avenue Hotel’s Bar Director. 

An industry veteran, Darryl infuses his cocktails with a deep nostalgia for old-school bartending and an undeniable flair for the inventive. Echoing the bar’s name, each drink he crafts is like a finely painted portrait, capturing a unique story through a balanced blend of flavors and aromas that evoke a sense of place.

The Evolution of a Bartender 

Darryl grew up on Long Island, New York surrounded by good friends whose families ran bars – giving him an early taste of the industry he now leads. “Watching them run a whole operation—from holding court to stocking bottles, breaking up fights, and cleaning up after a long night’s service—was incredibly humbling, yet powerful,” Darryl reminisces. 

These formative years unknowingly laid the groundwork for his fascination with hospitality and bartending. As he moved beyond the neighborhood bars of his youth, Darryl’s passion for mixology took off during the early days of the craft cocktail movement in 2009. Frequenting iconic bars like PDT, Clover Club, and Death & Co, he was mesmerized by the artistry and sophistication of the cocktail scene.

Although Darryl initially planned to attend culinary school, his path shifted when he jumped directly into New York City’s high-end restaurant scene, initially working with Michelin-starred Chef Daniel Boulud’s team at Boulud Sud. But it was at the renowned restaurant Daniel, under the mentorship of Xavier Herit, that Darryl further honed his skills within a regimented yet creative craft bartending environment.

“It’s when I was a bartender that I felt most accomplished. Compared to other jobs in hospitality, I was able to put more tools in my belt in terms of my craft, and that’s how I fell in love with it,” Darryl explains. 

Crafting The Portrait Bar Experience

Darryl first crossed paths with Chef Andrew Carmellini when Darryl was working at Café Boulud—the same place where Carmellini had previously been the Chef de Cuisine and collected two James Beard Awards. “AC [Andrew Carmellini] and I hit it off immediately,” Darryl recalls. Life has a way of leading you back to people, and this connection eventually resulted in consulting work with NoHo Hospitality. Then, in June of 2023, Darryl joined Carmellini’s opening team at The Fifth Avenue Hotel.
For Darryl, being a part of The Portrait Bar has been a deeply rewarding experience. Reflecting on the journey, he shares, “It’s seeing the product come to fruition, especially how beautiful this place is. When I first saw the mock-ups and renderings, I thought, ‘That’s crazy, there’s no way.’ But once you step into the space, it all comes together, and you realize it’s even more gorgeous than the pictures.” This sense of wonder and accomplishment is felt throughout the bar.

Reminiscent of London’s finest hotel bars and inspired by Italian villas, The Portrait Bar takes its name from the more than 50 portraits of diverse individuals from different eras and styles, echoing the eclectic mix that defines New York City. The bar’s design and its flâneur philosophy—embracing the art of leisurely exploration and observation—inspired the menu. “Over the course of the menu development process, we considered countless places all over the world for inspiration. It’s what New York is—people coming from everywhere, and we wanted that to feed into the guest experience here,” Darryl explains.

Darryl often starts the creative process of building an impactful cocktail experience around a specific ingredient or an impactful moment. What follows is a well-thought-out mix of traditional techniques coupled with innovative practices like sous-vide and clarifications. The Mapo District, a drink inspired by the flavors of Seoul, Korea, encapsulates this vision. 

“We do a little sesame oil fat wash on the Laphroaig Scotch and mix it with Tokki Soju Black, which is made locally in Brooklyn in the traditional way. Then, we add pineapple and cucumber. On paper, the process sounds unconventional, but with this, it becomes rich, umami, but still refreshing.”

Another one of Darryl’s signature cocktails is the Barrio Getsemani, a crisp martini inspired by Cartagena, Colombia. This drink blends tropical freshness with the sophistication of a martini, adding a surprising twist by using aguardiente, an anise-flavored spirit local to Colombia known as ‘firewater.’ “When you’re in Cartagena, you usually get a drink with fresh juice and ice. It will be delicious, and you’ll want five of them. I wanted something a little more understated in appearance but packed with those flavors,” Darryl says.

Beyond technique, Darryl strives to create a unique experience that people can connect with, whether they’re seeking the hottest new spot or are locals looking for a place to feel at home. He and his team are not just alchemists behind the bar but also gracious hosts. “It’s like you’re in our living room, and we just want to take care of you,” he adds.

Looking to the Future

Being named one of Esquire’s Best Bars in America 2024 is a significant accolade for The Portrait Bar and proof of the hard work and vision of Darryl and his team. “It’s truly humbling,” he says. “After a short amount of time, people are really appreciating what we’re trying to do.”

Looking ahead, Darryl is excited about the future of The Portrait Bar. “We’re still trying to see where this can go,” he says. With Darryl at the helm, The Portrait Bar is set to evolve and enchant, making sure every guest feels a part of its ongoing story.

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