Nearly a decade separates Andra Day’s 2015 debut Cheers to the Fall and her second album of original material, CASSANDRA (cherith)—but such are the consequences when you become a multidisciplinary crossover star who crafted one of the most uplifting anthems of the Black Lives Matter era (“Rise Up”), got invited to perform at the Biden/Harris inauguration, and won a Golden Globe for portraying one of the greatest jazz singers of all time (in 2021’s The United States vs. Billie Holiday). With CASSANDRA (cherith), Day makes up for lost time in the most wonderful way, by crafting an epic song cycle that perfectly balances elegance and attitude. As Day tells Apple Music, her engagement with Billie Holiday’s legacy didn’t end once the cameras stopped rolling. “A lot of her spirit and a lot of that music and her feeling found its way onto this project,” she says. “Not necessarily sonically, but through attitudes and mentality and the things that I'm saying. I'm a little less apologetic here for sure.” Over the course of its 16 tracks, CASSANDRA (cherith) charts Day’s soul-cleansing journey to rid herself of dysfunctional relationships and toxic influences and carve out some inner peace in her whirlwind life. But from that thematic focal point, Day ventures out in myriad musical directions, complementing her theatrical retro-soul showstoppers (“Probably”) with tropical piano-jazz reveries (“In the Meantime”), smoky after-hours torch songs (“Where Do We Go”), and old-school hip-hop flavors (courtesy of guest rapper Wale on “Heavy on My Mind”). “My main thing with this record is that I really wanted to chase down everything that I loved,” she says—and with CASSANDRA (cherith), Day gives us nothing less than a 360-degree view of her life and art.