Nearly a decade has passed since multifaceted songstress Andra Day burst into the consciousness of music listeners through her breakout single “Rise.” Featured on Day’s 2015 debut album, Cheers to the Fall, the multi-platinum-selling song has been used for everything, including graduations, sports highlights, elections, and anything that celebrates incredible triumph. 

A lot has changed for Day and the music industry between now and then. When she wasn’t collaborating with artists ranging from Robert Glasper to Sheryl Crow, BJ The Chicago Kid, and Raekwon, the singer-songwriter has been making a huge push for Hollywood. This includes her 2021 breakout role as jazz vocal legend Billie Holiday in Lee Daniels-directed “The United States vs. Billie Holiday.” Not only did Day get a Best Actress nomination at the Oscars, but won a Golden Globe for Best Actress in addition to the soundtrack, winning a Grammy for Best Compilation Soundtrack for Visual Media. That doesn’t even count the Children’s and Family Emmy Award for her work on “We the People,” in which she served as both writer and performer of the song “All Rise.”

The first half of 2024 saw Day sing the “Black National Anthem” during the Super Bowl while also releasing several singles, including “Where Do We Go,” “Probably,” and “Chasing.” Those tracks would be featured on her sophomore follow-up to Cheers to the Fall through Cassandra (Cherith), released in early May. According to Day, she finally had time to concentrate on a full-length project. 

“Me and the team carved out a window of time but I never wanted to stop doing music,” explained Day to BET.com. “The movie things sort of just infiltrated and were like, this is what we’re going to do right now. When they were calming down, I could feel that feeling like I really wanted to finish the record and get it out. I think all of that had to happen in order to inform the album.” 

Day acknowledged that those experiences profoundly shaped Cassandra (Cherith), emphasizing that the transformative nature of these events compelled her to be present and introspective. The album is based on her actual legal name mixed with something spiritual. That creative process involved writing about the impacts of various life events such as movies, lost love, and both causing and enduring hurt. Additionally, Day’s spiritual growth and experiences of divine love significantly informed their project, culminating in a cohesive final work that made sense to them. Even the art direction of Cassandra (Cherith) features Day on a desert-themed backdrop draped in old Cheers to the Fall tour merch. Being a deeply devoted Christian, she was inspired by the Biblical story of Elijah cutting away at brook Cherith in isolation.

“The desert water things are kind of me on my journey to a place of wilderness which to me represents a place of lack,” Day said. “This idea that I go into spaces feeling like I’m not worthy. Even though I tell myself yes and just show up; we do a lot of showing up anyway.  That I really have everything I need, not just inside me, but my community. I have what I need; the people around me to do all the things that I need to do, and now I'm called to do it. So the album is told through the form of relationships, through love, through my own journey and spiritual growth.”

Initially, Day intended for Cassandra (Cherith), which saw her recording around 100 tracks(a blend of demos, some finished and half-finished), to be a cultural statement about people, aspiring to create anthems and make impactful statements. However, her actual process and inspiration differed significantly. Reflecting on her hit "Rise Up," Day noted that it emerged not from a deliberate intention to inspire but from a personal moment of intense emotion, questioning her career, and seeking divine guidance. This realization influenced her approach to her current project, where she aimed to discuss culture and life deeply but found herself redirected by her experiences and spontaneous creativity. Though Cassandra features that classic vintage and jazz sounds that have become a calling card for Day, she also experiments on the album with more R&B, neo-soul, funk, hip hop (rapper Wale is the sole feature on the project), and more this time around. 

“I love futuristic things and sounds of nature,” said Day. “I love sounds of space and I love the sounds of vintage Star Trek.  just let all of those things come forth and just what's going to come out is what's going to come out. I didn't go, I'm making an R&B record. I'm making a soul record. I'm making whatever, hip hop. It just was like; sound.”

That goes for the songwriting as well, which saw Day collaborate with co-writers Jacques Pierre, Kendra Foster, Jesus Delgadillo, and more. According to Day, she loves singing about things that are based on personal experience on both micro and macro levels. 

Though Day is in full album roll-out mode for Cassandra (Cherith), she’s still working up the Hollywood ranks. Alongside starring in the upcoming Titus Kaphar-directed “Exhibiting Forgiveness,” she’s relinking with Daniels again for the supernatural horror film “The Deliverance” alongside Mo’Nique, Omar Epps, Octavia Spencer, and Glenn Close. Day says that Daniels approached her with the film idea while working on “The United States vs. Billie Holiday.” 

“He’s my Scorsese,” said Day. “When people look at all these great directors, there’s nobody in my opinion that is able to pull performances out of actors the way Lee does. Whatever he wants to do, is something that I want to be a part of because he’s a genius.”

Day described her current phase in life as the beginning of a new book, acknowledging the cyclical nature of life and how her latest album represents one such cycle. She humorously noted the frustrations of encountering similar challenges as before. However, Day mentioned working on music, including collaborations with Terrace Martin, Robert Glasper, KING and even a possible collaborative EP with Wale. 

“I feel like I'm at chapter one of a brand new book, and we will be getting more music," said Day. “This season in my life, I'm just like, just go. Just go and just say yes, trust God. You're supposed to be there for a reason. Even if it's not for a song, maybe it's for the interaction.”