While You Were Sleeping: Chessa Rich’s Dreamy Sound

The Durham-based singer-songwriter’s first album, Deeper Sleeper, draws atmospheric pop from her dreams.
by David Menconi | photography by David Tesh

It’s common enough for artists to take a while to realize the underlying inspirations behind their own records, often years after the fact. Still, Durham musician Chessa Rich’s odyssey with her first album makes for an unusual story.

Thanks to the input of supportive musical friends from Mipso, Hiss Golden Messenger, and other local acts, making her full-length debut was “super exciting, almost like summer camp,” Rich says.

The album is a very fine nine-song collection of atmospheric pop songs, keyed around Rich’s piano and agreeably smoky voice. But it wasn’t until later, when Rich took a class at Durham’s Night School Bar, that she figured out her album’s throughline.

“The class was about dreams, art and interpretation, and it made me realize that all my songs had come from this place of dreams,” Rich says. “I’m kind of still processing that. I’ve always been a very vivid dreamer, which I don’t think will ever end. I feel very tied to sleep and resting and dreaming. Even when I write about something else, that still informs how I go about my day and my life, with energy and drive and motive and inspiration.”

But Rich has never been the best sleeper. After this realization about her album, she was diagnosed with sleep apnea, a disorder in which a sleeper’s breathing can stop. So she decided to call the album Deeper Sleeper, and it has a far- away ambience like the morning haze of half-remembered dreams that leave you with more feeling than narrative.

“If you die in your dreams,” Rich declares in the song “Wanderer,” “you don’t die in real life.”

“I’ve known Chessa for a while and I feel like her record manifests all her strengths,” says Gabe Anderson, a co-founder/co-owner of Sleepy Cat Records, which released the album, and who also plays in Rich’s live band. “One song, it feels like a pop record. Another, it’s really tugging the heartstrings. I think she’s deserving of the biggest stages on the planet. She can deliver the biggest pop ear-candy experience, and also the smallest personal experience.”

Now 35 years old, Rich was born and raised in Burlington. One of her earliest musical memories was her father show- ing her how to pick out the intro to Led Zeppelin’s “Stairway to Heaven” on the piano when she was a kindergartener.

Rich played flute and piccolo in the high school marching band, rising to the rank of drum major by her senior year (a role her father had at the same high school decades earlier). Piano eventually became Rich’s primary instrument, but she still plays in a flute quartet called SCRS (pronounced “Scars”) with her fellow local flutists Skylar Gudasz, Rachel Kiel and Steph Stewart.

After college at the University of North Carolina at Chapel Hill and two years teaching English in Spain, Rich moved back to the Triangle about a decade ago. Working as musical director in local churches introduced her to other players on the scene, and she became a familiar sight onstage in support roles for local peers like Kate Rhudy. She still plays the church circuit while teaching piano to kids as her primary job.

“A lot of cartoon themes and Taylor Swift songs,” she says with a laugh.

Rich hopes to release a few more songs this year, followed by another full-length album whenever time and finances allow. She hasn’t yet been able to tour widely, but her local reputation is growing with sold out shows and a Hopscotch Music Festival main-stage booking last year.

“My album-release show at Cat’s Cradle Back Room sold out, and packing my favorite local venue was a dream come true,” she says. “The music industry’s in a weird place right now, because it’s very expensive to do anything like tour with a band. Someday, I hope. But I am super thrilled with the local response.”

In reviews of Deeper Sleeper, Fiona Apple’s name frequently comes up as a point of comparison. The album’s overall feel is also reminiscent of Joni Mitchell — although Rich feels that influence is more about attitude and motivation than musical sounds.

“Joni Mitchell is awesome, but I would not consider myself a Joni follower in the same way as a lot of my friends and collaborators,” Rich says. “I am mostly interested in her as an artist, being so fully honest in her writing. I saw a recent interview where she said she doesn’t understand people who claim to have nothing to say: ‘They’re just afraid.’ She was adamant that every single person has something to say and if they don’t, they’re just shying away from it.”

Meanwhile, looking ahead to where the next batch of songs might take her, Rich reports that her relationship with sleep is much improved nowadays.

“Better than ever, I am happy to re- port,” she says with a laugh. “The CPAP machine helps, although not as dramatically as I hoped. I’ve just realized I really need 10 hours of sleep a night, which can be frustrating. My day has two or three hours less than most people. But we do what we can.”

This article originally appeared in the March 2024 issue of WALTER magazine.