Caitlin Sherman Faces Challenges Big and Small with “Up The Street, Diving Down” Video Premiere

For Seattle songwriter Caitlin Sherman, 2020 was supposed to be a transformative year for her music career. She’d just recovered from two break-ups—of her band, Evening Bell, and of her relationship that anchored that band—and recorded her transcendent debut solo release, Death to the Damsel, which she dropped like a Valentine to herself on February 14th, 2020.

Then, just as she was getting on the road to tour with her original psych-country album, the pandemic ended her release tour and forced her to turn back for Seattle.

“It was heartbreaking to be on the road and have to turn around after so much planning had gone into my album release year. And it quickly became very clear that playing music and performing was my coping mechanism for a long history of depression and past trauma,” she tells Audiofemme. After coming to that realization, Sherman decided to make 2020 transformative in a different way than she’d planned—she started addressing her mental health and really assessing the reasons she makes music.

“I was able to take a step back and reflect,” she remembers. “At the start there was this deep sense of dread. Why is music even important while the world is falling apart? Will people even miss live shows? Is art important?”

Setting out to answer those questions and determined to make the best of her botched release year, Sherman found ways to be there for others (and show up for herself) with her art. In that spirit, she’s releasing the never-before-seen video for “Up The Street, Diving Down,” a single from Death to the Damsel, with Audiofemme today.

“Up The Street, Diving Down,” which Sherman wrote after the end of her long-term relationship, is a story of doing the sensible thing and staying in—despite the urge to go out and do shots with your old flame.

“I really hadn’t been single my entire adult life. So at 34, I was learning how to navigate that and also process the two back to back romantic/creative partnerships I had,” she explains. “The joke is that when old ladies say they are going ‘sailing’ they mean they are going to garage sales. So when I say ‘diving’ it means going and drinking at dive bars [when] the subject of temptation is in your neighborhood at the bar.”

Characterized by Sherman’s cheeky vocals and moaning Telecaster, the song captures her tongue-in-cheek desperation: the lyrics cleverly describe pouring salt in the doorway and even locking herself “into her nightgown.”

The concept for the video is similar, showing Sherman “left to her own devices,” distracting herself from temptation. Videographer Ryan Jorgensen shows Sherman in several charming and relatable scenes—playing chess with herself at the dining room table, bouncing on her bed with a hairbrush microphone, embracing a plastic mannequin on a velvet couch.

Written before quarantine was in full swing, the song now holds even more resonance for Sherman and listeners—as we’ve all become masters of finding unique ways to stay entertained in our homes in the COVID-era. For the video, which Sherman filmed while housesitting for her friend Brent Amaker (of Brent Amaker & The Rodeo) in 2021, Sherman says they wanted to play with that shift in the idea of staying in.

“To lift my spirits at the year anniversary of my debut album, I asked permission to use his house as the setting for the video. And boy, did we use it as much as possible. [We did a] twelve-hour shoot [in] multiple rooms, and [with] costume changes,” she says. “Kate Blackstock painted the mannequins; they are meant to be my ‘companions’ while isolating. We shot some far more creepy scenes with them but that didn’t make the cut. Had to ask ourselves wait… is this weird? Our collective gauge on sanity may have been a bit off in early winter of 2021.”

Nearly two years since she first released Death to the Damsel, Sherman shares this video in celebration of the song, which never really got its fair shake—and of being recently named one of Seattle nonprofit Black Fret’s 2021 grant recipients. With the $5000 grant, Sherman is looking forward to the future and planning to use the funds to record her next album—which promises to be a doozy.

“I have songs that I’ve been collecting for the past few years for my next album. A different phase of life provided for plenty of inspiration,” she teases; she’ll perform old and new favorites when she opens for Chuck Prophet at Tractor Tavern on February 25th. “In the darkest moments of isolation and the craziness of the past couple of years, I managed to keep playing and writing. Not every day, and not without dry spells, but I pushed through as best I could.”

Follow Caitlin Sherman on Instagram for ongoing updates.

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