Album Review: Cassandra (Cherith) by Andra Day

A thorough traverse through her encompassing 16 tracks, Cassandra (Cherith) delineates the cathartic passage of Andra Day that strives to purge the residue of unhealthy relationships and more.

Courtesy of Warner Records.

Andra Day’s vocal acrobatics resonate with striking depth, a riveting symphony of influences echoing Jazmine Sullivan, Amy Winehouse, Erykah Badu, Esther Phillips, Dinah Washington, Ella Fitzgerald, Bessie Smith, and Billie Holiday herself. Day’s portrayal of Holiday in the 2021 film The United States vs. Billie Holiday won her a Golden Globe and formed a profound connection between the two artists as Day navigated Holiday’s unique blend of vulnerability and tenacity. 

Day’s debut album, Cheers to the Fall, released in 2015, showcased her stupendous vocal prowess and introduced dramatic, retro-style tracks. Among its gems, the song “Rise Up” emerged as a Black Lives Matter anthem in 2020. American music history is filled with examples of blues, jazz and soul singers skillfully employing the jazzy quaver to convey intricate emotional shades, and Day revitalizes this tradition in her second album, Cassandra (Cherith), offering an expansive range of emotions. 

In the wake of Cheers to the Fall, Day brought out a Christmas EP in 2016 featuring a duet with Stevie Wonder and released a range of singles and soundtrack songs. With Cassandra (Cherith), Day reveals a treasure trove of new material, having lent her skills as a writer and producer to all 16 tracks. The new album candidly explores themes of romantic and emotional entanglements, navigating the labyrinthine journey from tormented separation through the challenges of making a fresh start to the ultimate destination of self-acceptance. 

Distinctive from the retro ambiance of Day’s debut, Cassandra (Cherith) draws attention to intricate details through a close-up approach, throwing Day’s audacious voice into sharper relief. Throughout the album, she maintains a risky, explorative vocal style. Day’s mastery of melody permits her to freely adorn and adjust her tunes, her movements fluid and instinctive. She smoothly integrates various styles and epochs, from neo-soul underlined with hip-hop rhythms to jazz, Motown, bossa nova, piano rock and vintage orchestral pop. However, it’s her voice, precise yet unrestrained, carefree but intimate, that steals the show. 

Her album opens up with a slow-burning R&B groove, “Maybe Next Time,” that navigates the emotional turmoil of a troubled relationship, and sets a tone of frustration and disappointment, as she has repeatedly convinced herself and others that this relationship would be different, only to find herself proven wrong. The same goes for the Latin-infused mixed with neo-soul, “Narcos (H.C.D),” where Day reflects on the cyclical nature of their mistakes (with themes of insecurity of jealousy), indicating that despite time passing, there is no growth or change in behavior and repetition of destructive patterns leads to a sense of inevitability that divine intervention might be necessary to disrupt this cycle, as suggested by “Good God up above will bring heaven crashing down on us.”

With “More,” Andra Day explores the themes of vulnerability, desire, and the complexities of love. As the song progresses, there’s an expression of readiness to take action and pursue this love interest actively. She sees potential for growth and transformation through this relationship but also recognizes the inherent risks involved in becoming emotionally invested. The album’s first single and one of the clear standouts, “Where Do We Go,” captures the emotional tension between wanting to reconnect and understanding that some doors are closed, creating a narrative about the difficulty of moving on from intimate connections. The verses oscillate between desire and the recognition of an inevitable parting, highlighting an internal struggle with lines such as “I see love inside your brown eyes.”

The album holds a myriad of gems, from Day’s riveting performance on the captivating anthem “Probably” to the entrancing groove of “Nervous.” This album was titled after Day’s birth name and a biblical allusion to ‘cutting away,’ the album stands as her most personal work yet, highlighting her stunning versatility. Tracks such as “Heavy On My Mind” (featuring Wale) exemplify Day’s R&B proficiency. The soul-stirring ballad “Bottom of the Bottle” and “Still,” which highlight her strength as a vocalist, displaying her emotional depth. The album’s sonic spectrum is aptly represented by the third single, “Chasing,” a tender rumination on ambition and yearning. 

The album’s standout cut, "Champagne Flutes,” uses vivid imagery and metaphor to convey a message about authenticity and remembering one's roots amidst the allure of superficial glamor. The song reflects on lessons from the singer's upbringing, mentioning her mother's advice and a hero who drives a Cadillac—a figure who maintains skepticism about appearances. It’s a homage to staying true to oneself while navigating different social environments. It celebrates where one comes from while also acknowledging personal growth and change.

On the bossa nova-inspired “In the Meantime,” she explores the emotional limbo and introspection one experiences during a period of waiting or uncertainty. The song thus captures a snapshot of emotional complexity during times when we’re caught between phases in life or love. “About It” captures the intensity and depth of a romantic connection. Day uses spiritual language to describe her transformation through love. She speaks of seeing divinity in her partner’s actions, suggesting a redemptive quality to their love that has healed past wounds. This elevates the relationship beyond mere physical attraction or compatibility; it becomes a transformative experience.

The closer, “Thank You God (Mom Reading Psalms 62),” acts as a sequel to “Still,” reflects a theme of finding peace and stability through faith and self-affirmation. “Not lost in love but found in the relation” suggests that this love is not blinding or overwhelming; rather, it provides clarity and a sense of being grounded or anchored in relationship—whether that be with another person, oneself, or a higher power. There is an acknowledgment of divine support lifting one to higher emotional states, with joy and peace being linked to listening to a quiet inner voice—perhaps intuition or divine guidance. The closing lines from Andra Day’s mother reinforce these themes by drawing directly from Psalm 62, speaking to the steadfastness of God as a savior and protector.

Heralded as a compelling vocalist and masterful songwriter, Andra Day does not simply inhabit the realm of vintage R&B; she skillfully intertwines the depth of gospel, jazz, and blues in the past, manifesting them with remarkable agility and savvy, firmly anchored in the now. Within the scope of her latest musical offering, Cassandra (Cherith), Day employs her breadth of talent to traverse intricate emotional terrain, thanks to Caleb Morris, Jayla Darden, Dave Wood, Charles Jones, and plenty of others on production. She delves into the challenging dualities of personal yearnings met with public aspirations. Can she harmonize these seemingly conflicting spheres? Her commanding vocal expertise emphatically signals her capability. Presenting the most distinguished R&B album of the year, Day’s work stands in an echelon of its own.

Standout (★★★★½)

Favorite Track(s): “In the Meantime,” “Where Do We Go,” “Nervous,” “Champagne Flutes”