Teardrop Lounge’s Daniel Shoemaker Reflects on a Decade of Cocktails

When Daniel Shoemaker opened the now famous Teardrop Lounge in the summer of 2007, the idea of a dedicated cocktail bar was alien. The cocktail renaissance, a return to pre-prohibition styles and ingredients as compared to the 90s style of sugary mixers and vodka, had already landed in the city, brought by pioneers like Lucy Brennan of Mint/820, Ryan Magarian of Oven and Shaker, and Marco Dionysos of Saucebox, but those menus lived mostly in restaurants. Teardrop was something new, and would come to shape the cocktail scene of Portland in dramatic ways.

It didn’t start off a smash success.

“People were very resistant to what we were trying to do at the time,” says Shoemaker. “Our Yelp page was rife with complaints. People were pissed off that our tonic was brown, that we had egg whites in our cocktails.”

And at times it was deserved. “We had a Reuben cocktail with a devoted audience of five people. We didn’t have any guidance, anyone telling us we couldn’t do this or that. It was great for fostering creative development, but I’m glad we stopped that years ago.”

The bar earned a steady following, honing its focus and developing more balanced cocktails while remaining creative. Numerous talented bartenders came through Teardrop, and moved on to shape the Portland bar scene, including Dave Shenaut, Tommy Klus, and more.

“Evan Zimmerman showed up to his interview with his own homemade bitters.” Shoemaker says.

As Teardrop evolved and perfected its hundreds of cocktail recipes, the city changed with it. Bar after bar opened; cocktail programs launched at restaurants; and an obsession seized the city. Some bars were clearly influenced by the menu at Teardrop Lounge, with esoteric ingredients like gomme syrup showing up for no apparent reason. Three-column drink menus also appeared, mimicking Teardrop’s model of classic, house, and guest drinks.

For a while the Portland cocktail scene was more ambitious than well executed.

“There was obfuscation for obfuscation’s sake. I would see these seven-ingredient cocktails that were a mess. We were guilty of it at times, but that was in spite of ourselves. We always wanted to have three to four ingredients unless the cocktail absolutely demanded more.”

Dina Avila/EPDX

Nowadays though, things have changed. “What we’re seeing is less adventurous and more accomplished, a stabilizing of the industry. It’s common for people to expect a caliber and a level of expertise. That’s the most revolutionary thing: That you can walk into most any bar, order a negroni or an old-fashioned, and get something good.”

As for how Teardrop remains as relevant as it does in a city inundated with great bars, Shoemaker says, “That’s a corollary of passion breeding passion. Everyone who comes on at Teardrop partakes in that. And we’re still on the forefront because we’re always changing. We change the menu every few months.”

He also describes Teardrop as one of the only cocktail bars in the city, based on the reality that ninety percent of its sales come from cocktails, whereas other bars with great cocktail programs have a much larger focus on food, or beer and wine. The description seems accurate, as only a handful of other Portland bars likely operate with a similar business model.

“We would have been irrelevant years ago in a major city,” Shoemaker adds, with signature self-effacement.

Others would likely disagree.

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