The Evolution of Portland's Teardrop Lounge, One of America's Most Important Cocktail Bars

With a new menu that celebrates the classics, cutting-edge Teardrop Lounge keeps things fresh by looking back.

Teardrop Lounge
Photo: Courtesy of Teardrop Lounge

Ever since Daniel Shoemaker and Ted Charak opened Portland, Oregon’s Teardrop Lounge in 2007, it’s been known for stellar cocktails constructed with house-made or hard-to-find ingredients. The piña coladas are made with house-roasted coconut and freshly-squeezed pineapple juice, while original cocktails come with everything from Amer Picon, a French bitter made from orange peels that isn’t commercially available in the U.S., to costus root bitters, which combines a medicinal herb native to South Asia with rye whiskey and ginger.

Every three months, the list of about 30 cocktails—broken into roughly equal sections of House Cocktails, Classics, and Friends (favorites from other bartenders)—changes. But later this year, they’ll be deviating from the norm to launch a completely revamped menu that will include “a broad swathe of our canon from over the years,” says Shoemaker. “With the new approach, we’ll have the ability to rotate a hyper-seasonal selection of drinks, while offering a more static repertoire of inspirations from our curated Rolodex.” In other words, you’ll soon have the chance to flip from Teardrop’s greatest hits to their latest work, and back again.

For such a forward-looking bar to take pause and celebrate its past proves what any cocktail aficionado knows: Teardrop Lounge is one of America’s seminal bars. It’s a living classic.


When they left San Francisco for Portland in 2006, Shoemaker and Charak had no craft cocktail bartending chops—they’d spent their careers serving beer and shots. At first they had planned to open a neighborhood bar with a large selection of sake. But construction delays left Shoemaker with time to reconsider and pivot after having an a-ha moment while researching craft cocktail recipes. “I can make all of this,” he told himself. “I’d been cooking for a really long time and realized you could apply the same principles from the kitchen to the bar.” When Shoemaker opened the bar, he started making everything from scratch and things just “spun out of control from there,” he says. “We were always up on two wheels because we didn’t have a guiding principle.”

It might be common practice today, but it was a unique approach at the time, and word quickly spread. “In addition to fresh ingredients, they were getting experimental, making their own syrups, tinctures, bitters, etc. and also introducing people to forgotten classics,” says Karen Foley, founder and publisher of Portland-based Imbibe Magazine. It soon became a destination for curious bartenders from out of town. “Everyone who came up from San Francisco was like, ‘Whoa,’” says Shoemaker. “Their [SF] model was two spirit, one citrus, three-quarter sweetener, and have a little fun with that. We were on some other level.”

Teardrop Lounge Bar Area
Courtesy of Teardrop Lounge

Charak left the bar after two years, and Shoemaker's been running the show ever since. Eleven years after opening, Teardrop Lounge is still wowing imbibers, and it’s in no small part to the team that Shoemaker has assembled over the years. The opening bartender was a brash, young local named David Shenaut (now a partner at Portland’s Raven & Rose). “We were slammed every night and then sitting down brainstorming,” says Shenaut. “Daniel had these coasters where he was writing things down, sticking them in his pocket, and the next day, the change would be made. That was the environment that was created.”

Tommy Klus traded in bartending in a traditional fine-dining setting for the chance to join the team. “I remember a feeling of wanting to break the code,” he said. “Teach me everything you know.” Klus has gone on to consult on many highly regarded Portland bar programs, including the Multnomah Whiskey Library, and is now a partner at La Moule.

Mary Bartlett started at Teardrop in 2009 and quickly graduated from cocktail server to bartender. She persevered through both her own inexperience and Portland’s “boys’ club” bar scene because “it was just such an honor to be back there.” Bartlett eventually moved to Los Angeles, where she now runs the bar program at the Ace Hotel.

But the bar attracted plenty of experienced craft cocktail bartenders too, including Ricky Gomez from Cure in New Orleans (now owner of Palomar in Portland), and Sean Hoard from PDT in New York. Both had polished skills behind the bar but wanted to learn the dirty work that turned good bartenders into great ones. “My mentor and now great friend, Jim Meehan [owner of PDT and now a Portland resident], told me there were two people I should try to work for when I moved to Portland: Daniel Shoemaker and Jeffrey Morgenthaler [of Clyde Common]— and I got to do both,” says Hoard. “The cocktail program at Teardrop has always beenfearless and unfettered. That approach can be intimidating at times, but for those who embrace it, the program generates a seamlessly endless fount of new, engaging, and original drinks.”

Current head bartender Alejandro de la Parra had been a barista before coming to work for the bar. “Daniel hired me as the first doorman for Teardrop,” he says. “I worked a summer, and apparently weaseled my way into his heart. Enough that he would pluck me from the mud, and form me into a functional bartender.”

De la Parra carries on the tradition of pushing the envelope with creative and complicated drinks. Take his “Empire of the Sun” cocktail, which will debut as part of the revamped menu later this year. “It is a funky twist of culturally distinct flavors that harmonize to make an Eastern-styled Bloody Mary,” he says. He combines Ransom Old Tom gin, lemon juice, agave, and muddled cucumber with a take on harissa, where “umeboshi and santaka peppers form the base flavors for the drink.”

Teardrop Lounge
Courtesy of Teardrop Lounge

Beyond all the prolific bartenders that the bar has turned out, Teardrop has also given rise to an unparalleled resource for Portland’s bartenders. In 2014, having cemented a reputation as an innovator of house-made ingredients, Shoemaker partnered with Hoard to open The Commissary, which supplies unpasteurized juices, along with bitters, cordials, and syrups, to dozens of Portland bars and restaurants. It’s been so successful that it recently expanded to Oakland, California.

“In the midst of my tenure as manager, Daniel and I discussed opening a bar together,” says Hoard. “In doing so, we realized that we’d need a shared commissary kitchen between the new bar and Teardrop (I’d been spoiled by the wealth of house-made ingredients he put at our disposal daily). This realization sparked an idea: that others would obviously also benefit from such a service.”

“It’s the part nobody wants to do but is now what every cocktail program needs to do to operate,” says Shoemaker. “We have 50+ ingredients in our portfolio. We want to foster the bartender’s creativity by making something exactly as they would make it, invisibly. Then they could just build [their drinks] on top of that.”

It's this dedication to the craft that has kept Teardrop on the cutting edge for more than a decade.


Today, however, the experience at Teardrop isn’t just about the cocktails. “I think our service has stayed great, but has now adapted to a culture where cocktails don’t have to fight for relevancy,” says de la Parra.

As Shoemaker puts it, “The force driving business today is the unique, tailored experience our guests receive by a staff that’s genuinely excited to guide them toward the right cocktail for them in any given moment, to help them explore the full spectrum of drinks and identify the surprising pliability of their own flavor profile preferences."

Indeed, in taking a breath to recognize the ingenuity that’s been second to none, the bar has been able to progress and focus on perhaps the most important homegrown ingredient of them all.

“There is no need to brandish our cocktail wizardry like a weapon anymore; instead we can focus on caring for our guests' hearts.”

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