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Winterlark on “When I Saw You Stranded There” and the Delights and Fears of Songwriting

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Folk-jazz band Winterlark sets the scene: two strangers, a hot idling day, stranded in traffic. The speakers spot each other between the cars, a half-glance between sirens. And suddenly, everything changes.

The song, titled “When I Saw You Stranded There” tells a meet-cute love story with vivid energy. Kristin Olson plays the upright bass and croons in harmony with Sweeney E. Schragg. Schragg plays the guitar, breaking into a dance-worthy solo midway through. These San Francisco Bay Area singer-songwriters know how to tell a story. The song is punctuated with details that bring the lyrics to life: “Your radio was all I heard/I started reading bumper stickers/I read a second time, a third.” 

As the speakers notice one another, the other drivers stuck in traffic make the most of being stranded. A stranger “broke out his saxophone” and “two strangers tried to sing along” as the trapped drivers goofed off across the cars. Winterlark tells the story with affection, draping the soundscape in a warm, nostalgic feel. Schragg and Olson’s vocals blend together with cozy chemistry, creating a sense of familiarity which suits the story. 

While the strangers break into song, the speakers continue looking at one another. One of them shrugs their shoulders and starts to dance. “I had to show you how it’s done,” they sing gleefully. “After the gridlock lesson, I’ll never dance with another.”

“When I Saw You Stranded There” seems, ultimately, to be a song about strange and wonderful connections. It is nostalgic, silly, and casually joyful. We had a chance to speak with the folk-jazz band—here’s what they had to say.

When and why did you start making music together?

Kristin Olson: We first met on August 26th, 2018, at a jam in a backyard aikido dojo owned by a fiddler friend. I had no agenda. I showed up merely to distract myself from life. In contrast, Sweeney had been on a search for a female upright bass player that could sing. Turned out, I fit the bill, and life took a surprising musical turn that was exactly what I wasn’t looking for.

How do you go about storytelling in your songs?

Sweeney K. Schragg: I like to have a few words that give me a direction to write in. Often these are a good title. Then I have to have sensory detail for the story to live in and, of course, characters that intrigue me. Then I follow the characters around, see where they go.

KO: I am new to this craft, but I usually figure out what the heck is happening to the characters in the song, then imagine myself in the shoes of these characters and invent small details that might be in their lives. Once the visual is present, it is easier for me to fill in the action.

What delights you and what terrifies you about the songwriting process?

SKS: There are many little delights, the marrying of a line of words with a phrase of music, the discovery of a new chord progression, but the big delight comes when the song takes shape and I am able to hear it for the first time as an integrated whole. The terror is the empty page and a deadline.

KO: Songs that come from within – about my own life experience – can be delightful because there is often an easy upwelling of ideas, but they are also terrifying because, as a private person, I feel so exposed.

Where do you draw creative inspiration?

SKS: I am hyper-focused on language, always ready to steal an interesting turn of phrase uttered by a friend or a complete stranger. Kristin inspires me, because we toss phrases back and forth all day long, it seems. And I noodle on my guitar a lot, waiting for musical surprises.

KO: Oftentimes through observation of the world around me while biking or walking. I watch the way people walk. I look in the gutter.

What does Winterlark have coming next?

SKS: An EP with “When I Saw You Stranded There” as title track will be out in October, and we’ve begun recording a second EP, which we will release in spring 2022. Meanwhile, we’re performing where we can in these challenging times.

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