Chessa Rich with Skylar Gudasz | Saturday, Apr. 29th, 8 pm | Cat’s Cradle Back Room | $15

Chessa Rich has been dreaming of this moment for years.

First came the metaphorical dreams: Rich began writing the songs on Deeper Sleeper, in fits and starts in 2017, eventually recording the debut album in March 2021. But it took two more years until the project emerged from its cocoon, dropping this Friday, April 7, on Sleepy Cat Records.

That long stretch aligns with a period of difficult yet vivid dreaming, during which Rich suffered from undiagnosed sleep apnea—a condition that causes a person’s breathing to stop and start throughout the night, preventing the body from getting enough oxygen. In some cases, it induces intense, often terrifying dreams; in others, it causes persistent fatigue. Rich was unlucky enough to suffer a sucker punch of both symptoms.

“Not sleeping and being tired all the time affects your mood and changes your relationship to people, work, and creativity,” Rich tells INDY Week over a freewheeling lunch interview in March at Wilson’s Eatery in Raleigh. “Everything feels more stressful.”

Finally undergoing a sleep test after a lifetime of unsettled rest, Rich received relief: a medical diagnosis that delivered a modicum of self-acceptance, along with a prescription for a CPAP machine to sleep better. “It was super helpful to realize that I’m not just lazy,” she laughs.

But struggling for so long to interpret the surreal symbolism of her dreams while cultivating a career as a working musician who needs 11 hours of sleep a night gave the 34-year-old Burlington native and decade-long Durham resident a singular perspective on “making it.”

“I got so used to waking up and feeling the same amount of tired as I did when I went to bed,” Rich says. “Our culture is all about that ‘rise and grind, entrepreneur!’ mind-set: working, exercising, socializing, partying. But it doesn’t have to be that way. Learning that I had sleep apnea allowed me to be more gracious with myself.”

Deeper Sleeper’s nine tracks are awash in such benevolence. Recorded outside Woodstock, New York, at Milan Hill Studios with producer Shane Leonard, the album is primarily built around catchy piano riffs, the instrument that Rich grew up playing. A tight-knit circle of North Carolina friends—Saman Khoujinian, Joseph Terrell, Alex Bingham, and Jay Hammond—helped her flesh out those compositions with elegant instrumentation.

Propulsive synths and jagged guitars undergird Rich’s unusual vocal stylings on “Paper Heart,” where she stretches simple lines like “I crossed a border / Turning your corner” into syrupy tongue twisters. Lead single “Sleeping Is Easier” is a straightforward banger, with drum crashes and a driving chorus soundtracking Rich’s lamentation that “ringing alarms don’t wake me up” as “I close my eyes and I turn it off / And bite the hand of a ticking clock.”

Offbeat songs like “River” and “Dirty Wine Glass” feature complex bass grooves and skittering beats that match Rich’s intricate lyrics. Call it progressive R&B, symphonic pop, or jazzy alt-rock—Rich says it’s all indebted to shape-shifting influences like Radiohead, Wilco, Loma, and Big Thief.

“I’m an indie kid,” she says, admitting to past struggles fitting in with the Triangle’s dominant Americana and old-time paradigm. “But I don’t want to feel like my music doesn’t have any roots. My friends reinterpret folk songs that are part of this long tradition or canon, and I’m like, ‘Hey, I want that too!’”

Another clear touchstone is the music of Fiona Apple, especially evident on “Red Sky,” which foregrounds Rich’s booming piano and unadulterated voice. The stark composition tumbles through shifting keys and time signatures before Rich reaches an intense denouement: “I was made for a different time / I’m slower than most / But I think I’m good / I know I’m good.”

Deeper Sleeper is bookended by bops that could easily soar to the top of algorithmic streaming services. On “Wanderer,” Rich narrates a period of living in Spain, in which she longed for connection but also honed her knack for capturing life’s incremental Proustian memories (“The curtains were pleated just like cardboard”; “I sure know how to have a good time / Like a dog following a patch of sunlight”).

“Vacation,” meanwhile, is one of Rich’s oldest yet breeziest songs. Conceptualized in a hotel conference room on a borrowed guitar while she was selling merch on tour with Watchhouse (then performing as Mandolin Orange), she finished it during a weeklong residency at Wildacres, a retreat center in the Blue Ridge Mountains. Getting accepted, she says, “was divine intervention—truly a life-changing week.”

Six years later, Rich’s life stands to shift again. Her upcoming album release show on April 29 at Cat’s Cradle Back Room is sponsored by WUNC, and she’s elated to get back on stage after a multi-month break. Yet she is candid regarding her anxiety about careerist considerations: marketing, promotion, video budgets, licensing, interviews, and the dreaded social media content-making.

“Creative energy to me is a physical thing,” she says. “I like moving my body on stage with other people. So this promo mode has been messing with my brain. When I’m not playing shows and only living on the internet, I feel terrible.”

Asked about other musical pursuits that bring her joy, she goes deep: jamming with her church band on Sundays, watching her dad play trombone in the Elon University Wind Ensemble, and teaching music lessons—her main source of income over the last few years while also a clear inspiration.

“I want my students to understand how music can help them live in the world,” she says. “I like to work around their idiosyncrasies and what they want to say. That reminds me how to make my own music and helps me stay in the right mind-set.”

Another mental trick? Rich’s morning pages, a practice inspired by Julia Cameron, author of The Artist’s Way, and captured in loving detail in the video for “Julia.” The placid rumination on creativity blooms into deserved self-actualization: “Why have I been trying so hard?” Rich croons. “Befriend the things that follow me around / And redesign the present for the making / The painter’s the creation, not the painting.”

Those lines provide a direct connection to Deeper Sleeper’s final track, “Mary,” which honors Rich’s grandmother. She had nine children, Rich marvels, but still painted strictly for enjoyment for decades. In 2018, after celebrating the 2019 release of Rich’s first EP, All the Love Anyone Ever Gave Me, Rich’s mother gifted her one of those paintings to remind Chessa of her own artistic power.

“It made me so emotional to be connected to my grandmother like that,” she says. “I’m a continuation of her art—but I never got to talk to her about it.” Tearing up, she continues: “I want to ask her all these questions: Why did you paint? How did you paint? What made you want to paint?”

Toward the end of “Mary,” Rich threads her own existential questions with those her grandmother may have asked herself. When she sings, “I’ve been recalling more things / My lifetime is in the palm of my hand,” the strength of this generational thread—and the fascinating way she wraps her voice around the word
“palm”—cuts deep.

The song continues for two more minutes, clocking in past six minutes in an extended wash of piano, synth, drums, guitar, and bass highlighting again the instrumental mastery of Deeper Sleeper. Will listeners make it far enough, to that moment when familial nostalgia, artistic authenticity, and innovation collide? With the album yet to drop, it’s still unclear. But perhaps those who do will feel compelled to drop the kind of comment peppering Chessa Rich’s YouTube page: “Here before this blows up.”

In her affable, disarming manner, Rich shrugs off such deliberations. “When I started this process,” she says, “I had a weird relationship with songwriting, where I felt like I didn’t deserve to do this. I wasn’t ready two or three years ago to step up and step out like this. Even after recording Deeper Sleeper [in 2021], I sat on it for eight months. I wasn’t ready to release it then!”

Still, she isn’t afraid to admit that this moment—this dream state she stands on the edge of—is scary. “Sometimes I wish I had done this 10 years ago,” she laughs. “But I’m ready now. I’m just trying to remind myself that this is the first album. In 50 years, this will be one set of songs on one record—hopefully the first of like 11 that I put out. But I’m gonna make another one. And then another one. That’s literally the only goal.”

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